sailboat airbnb key west

7 Airbnbs in Key West to Book for a Seaside Getaway

These waterfront condos, historic bungalows—and yes, even a sailboat—have top-notch ratings on airbnb..

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In the backyard of this bungalow, you’ll find a hot tub, an outdoor shower, and a private sundeck.

Courtesy of Airbnb/Corey Breingan

Key West is about 130 miles from Miami, as the gull flies, and only 110 from Havana. In many ways, the compact island city feels more like a free-spirited Caribbean micronation than a part of the United States. For generations, the continental U.S.’s southernmost town has attracted the likes of Ernest Hemingway, Harry S. Truman, and Tennessee Williams, who were drawn here by its trademark brand of nautically tinged, edge-of-the-world quirkiness. These days, you can still while away lazy days in the island’s historic gardens and museums or string together a pub crawl of Duval Street’s many dive bars and saloons .

While there are plenty of hotels and resorts crowded onto the island’s roughly five square miles, there’s no better way to truly feel like a salty-dog local than to post up in a vacation rental, including a waterfront condo, a historic bungalow, or even a sailboat. As you sunbathe with a copy of The Old Man and the Sea and a Hemingway daiquiri, you just might wonder how to apply for Conch Republic citizenship.

To save you from scrolling through hundreds of listings on your own, here are seven of our favorite Airbnbs in Key West.

Inside the 43-foot masthead sloop yacht Sailing Vessel Maruquis , which is bookable on Airbnb.

Courtesy of Airbnb/Daniel Wallace

Beautiful three-bedroom sailing yacht

• Highlights: Fishing and snorkeling gear, Yeti cooler, outdoor shower
• Book now: From $289 per night, airbnb.com

Get in the seafaring spirit of the Keys on the 43-foot masthead sloop yacht Sailing Vessel Maruquis , which is owned by a high school science teacher turned sailing captain. The surprisingly spacious interiors include three staterooms, a full galley, a salon, and two heads—and if you have no clue what any of those rooms mean, be sure to learn some basic sailing lingo before getting on board! The boat also comes equipped with a swim ladder, life jackets, and snorkeling gear in case you want to get up close and personal with the dolphins, manatees, and sea turtles that frequent these waters. Keep in mind this vessel is anchored just offshore from Key West (not docked), so guests will need to arrange water taxi service via Ship2Shore shuttle services for an additional fee.

There’s no second-guessing where you woke up with beachy touches like coral-print bedding and sea-blue walls.

Courtesy of Airbnb/Cindy Verne

Private villa steps from Duval Street

• Highlights: Bluetooth sound system, shared pool, barbecue grill
• Book now: From $789 per night, airbnb.com

You have no choice but to slow down to island time as you approach Villa Serendipity: After entering through a bamboo-lined tropical garden and past a gurgling fountain, you’re greeted at the front door by a statue of a tropical-drink-swigging parrot in a Hawaiian shirt and a bucket hat. The interiors are brimming with similarly beachy touches, like coral-print bedding, mosaics of crashing waves, and a seafoam-green mini fridge in the main bedroom. The rental is particularly well-stocked for new parents, thanks to a crib and a pack and play. Also useful are the complimentary beach bag, towels, umbrellas, and snorkeling gear, which means you can leave several bulky items from home off your packing list .

This Airbnb’s backyard has a hot tub, but its front porch is also a prime spot for relaxing.

Hot tub home for six

• Highlights: Hot tub, washer and dryer, outdoor shower
• Book now: From $983 per night, airbnb.com

In her description of the property, host Corey Breingan describes her two-bedroom cottage as “crawling distance” from Duval Street—and with all those rum runners flowing at area bars, it’s a detail that might come in handy. At only 300 feet from the Key West Lighthouse and 500 from the Hemingway Home and Museum, the location is one of the strong suits at this blindingly white bungalow, which features a hot tub, an outdoor shower, a private sundeck, and a front porch for people watching. Inside, the vibe is understated tropical—we’re partial to the starfish-print chairs—with plenty of wicker and a cheerful sherbet palette. Note that if you’re traveling with a larger crew, you can rent the neighboring cottage as well, increasing the total capacity to 16.

If you book all three Airbnbs at Atlantis House, you have room for up to 10 guests to sleep.

Courtesy of Airbnb/Shari Ocampo

The Palm Suite at the Atlantis House

• Highlights: Cruiser bikes, backyard with grill, Bluetooth speaker
• Book now: From $464 per night, airbnb.com

Sleep under 17-foot vaulted ceilings in this detached bungalow that makes up one half of the Atlantis House’s guest suite, both sides of which are available for rent . (The main residence was also just listed on Airbnb.) The contemporary digs—with a crisp black-and-white design scheme—include useful touches like a mini Bluetooth speaker, cotton robes and bath salts, and a coffee pot stocked with Cuban beans. Bursting with tropical foliage, the shared backyard is a relaxing spot to unwind as you grill local pink shrimp, lounge on the chaises, or read in the shade of the gazebo, while complimentary cruiser bikes help you explore the surroundings, such as the White Street Pier one block away.

A cozy living room leads out to a private balcony at this condo near Duval Street.

Courtesy of Airbnb/Maja Williams

Downtown Duval Street condo

• Highlights: Private balcony, free beach gear, washer and dryer
• Book now: From $628 per night, airbnb.com

Homey and well-appointed, this cozy two-bedroom condo unit feels miles from the hive of activity on Duval Street, even though the nightlife corridor is just half a block away via an alley. The decor skews sophisticated with only the subtlest nods to the beachy surroundings, including a tabletop tic-tac-toe board that swaps out the Xs and Os for starfish and sand dollars. Digital nomads will dig the smart computer desk setup and the Keurig coffee machine; vacationers will appreciate the bookshelf stocked with board games and beach reads (think Danielle Steel and John Grisham). Bonus points for the ecofriendly Puracy toiletries.

The plunge pool at this penthouse Airbnb comes with a spa-like waterfall.

Courtesy of Airbnb/Barry Fitzgerald

Three-bedroom Duval Street penthouse

• Highlights: Heated pool, hammock, expansive kitchen
• Book now: From $788 per night, airbnb.com

Sprawling over 2,200 square feet of living space and an additional 2,000 square feet of porches and decks, this elegant two-floor property occupies prime real estate on Duval Street, with a balcony overlooking the ornate facade of the 1890 San Carlos Institute, a Cuban heritage center and museum across the way. Warm woods, rattans, and neutral-toned fabrics combine to create a breezy island atmosphere, with plenty of ceiling fans and nooks for quiet contemplation, from a hammock on the rooftop sundeck to a palm-lined plunge pool with a spa-like waterfall. Ideal for large groups, the space includes an outdoor dining table that seats eight, a crib, and a washer and dryer.

Anyone booking an extended trip to Key West will benefit from this Airbnb’s spacious kitchen.

Courtesy of Airbnb/Jenna Beldyga

Oceanfront beach club condo

• Highlights: Two pools, tennis court, fitness center
• Book now: From $828 per night, airbnb.com

Far from the scrum of historic Old Town, the Mid-Town neighborhood offers an oceanfront respite that’s more residential than rowdy. This two-bedroom unit in the Key West Beach Club will have you feeling like a local, thanks to condo complex amenities that include two pools, a tennis court, a fitness center, a sauna, and a shared outdoor cooking area. Inside, you’ll find yourself gravitating toward the spacious kitchen, with its large island that’s ideal for prepping fresh seafood or mixing a fruity cocktail, while the wide balcony looks out over swaying palms and a bathtub-calm stretch of the Atlantic Ocean.

At the time of publishing, these Airbnbs all have an overall rating of 4.90 or higher and all positive reviews from previous guests.

Vacation rentals in Key West

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Key West

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Bungalow in Key West

Atlantis House's Banyan Suite-voted top 25 in USA

About this space Atlantis House with just two exclusive rooms, the Master suite and the Garden suite, is the most private and romantic guesthouse in Key West. Rated a 2021 Travelers’ Choice Award by Trip Advisor. Perfect for Honeymoons and Anniversaries. A "little jewel" tucked away inside a lush tropical garden just steps away from the beaches. NOTE: Superhost Shari is a new owner of this property. Past reviews do not transfer but are 5-STAR! This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. Relax to island music on the Bose Mini Bluetooth speaker while you power up devices on provided chargers for countless photo op filled adventures that await! A corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee! Rejuvenate in the coveted in-room whirlpool bath with bubbles and soaking salts or cool off in the open shower with bench seating. The vanity is stocked with many toiletries and our white all-cotton bath robes allow for an extended spa experience. Please Note: The Banyan Suite is one of only two guest suites, separate from the Main Residence. The two suites have exclusive use of the lush backyard oasis with tropical trees, plenty of seating areas to enjoy the natural sounds of local wildlife or the pages of a good book. There is also a shared propane BBQ on the deck and an additional refrigerator with extra storage & ice located next to the complimentary cruiser bikes! The Banyan and Palm Suites each accommodate a maximum of 2 adults – Special accommodation for children may be included if the two guest suites are booked together. Guest access Guests have their own private entrance. Past reviews 5.0 out of 5 stars Cleanliness 5.0 Accuracy 5.0 Communication 5.0 Location 5.0 Check-in 5.0 Value 5.0

Nov 23 – 30

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Apartment in Key West

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Mar 16 – 23

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Key West vacation rentals

Stay near key west's top sights, houses in key west.

Home in Key Largo

Your Keys Getaway!

Jan 25 – Feb 1

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Oceanfront Tiny Villa in the Heart of the FL Keys

Sep 16 – 23

Beachfront Villa - Florida Keys

Home in Cudjoe Key

Paradise and Cudjoe Bay

Sunrise Beach Escape

Jun 25 – Jul 2

Cudjoe Key Home with a View

Marathon one-level home on the Marina - with slip!

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Jan 22 – 29

Waterfront Sunsets, Great Price, Relaxing Spot!!!

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Flakey's

Aug 17 – 24

The Gulf Cottage at Marathon Key

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

Condos in Key West

Condo in Key Colony Beach

Key Colony Beach Luxury Condo, New Modern Interior

Condo in Key West

Large waterfront 2/2 end unit with boat slip

Beachside Unit 28 - Private Beach, Pool & Paradise

Anchor Drop modern elegance upgrades throughout vi

Aug 11 – 18

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Condo in Marathon

Sombrero Beach Tropical Getaway

Condo in Tavernier

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Jul 30 – Aug 6

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Aug 22 – 29

Best View Ocean Pointe Pool Beach King Bed, Gated

It's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba

Condo in Key Largo

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

Feb 16 – 23

Tropical Getaway

Aug 23 – 30

Lake houses in Key West

Waterview from three sides, Cabana Club, 30' Docks

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

NEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART

Sep 13 – 20

Waterfront Escape -VACA-23-408

Apr 25 – May 2

Venture Out -Million Dollar Island Resort

Walk to Sombrero Beach, 50’Dock, SPA, Bikes,Kayaks

5 O'clock Somewhere - Key Largo

Apr 30 – May 7

Waterfront Key Largo Home - Tropical Paradise

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

5 O'Clock Somewhere Bay House, Drinks on Us!

Dec 16 – 23

Marathon Beach house w/45’ dock Ocean access

Tropical Waterfront, Boat Dock, Sunset View, Kayak

Jun 28 – Jul 5

Quick stats about vacation rentals in Key West

Your guide to key west, all about key west.

Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.

Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.

The best time to stay in a vacation rental in Key West

Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.

Top things to do in Key West

Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.

Ghost tours

Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.

Key lime pie

Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.

Frequently Asked Questions

How is the weather in key west.

Key West has a tropical climate with warm temperatures year-round. Summers, from June to August, can be hot and humid, often reaching 90°F (32°C). Winters, from December to February, are milder, with temperatures typically around 70°F (21°C), and less rainfall.

What are some of the best things to do in Key West?

Popular activities in Key West include exploring the vibrant coral reefs on a snorkeling trip, discovering local marine life at the Key West Aquarium, or visiting the historic Fort Zachary Taylor State Park. A stroll along Duval Street for shopping and local cuisine is also recommended.

What is the best time of year to visit Key West?

Key West is particularly lively between March and May, with milder temperatures and fewer crowds. During these months, you can enjoy events like the Conch Republic Independence Festival and the Key West Songwriters Festival.

What are the best places to stay in Key West?

Some highly-rated areas to stay in Key West include Old Town, a historic district with classic architecture, Truman Annex for its peaceful atmosphere, and New Town for its modern conveniences. Duval Street is also favored for its proximity to dining and shopping options.

What are the best places to visit in Key West?

Key West is known for diverse attractions such as the Ernest Hemingway Home and Museum, where the renowned author once lived, and the Key West Butterfly and Nature Conservatory. Don't miss the stunning sunsets at Mallory Square, and the view from the historic Key West Lighthouse. The Southernmost Point Buoy is also frequently visited.

What are some hiking trails in Key West?

While Key West is not known for its hiking, you can enjoy a leisurely walk at the Key West Tropical Forest and Botanical Garden. The Island City National Historic District also has interesting paths through the town's picturesque streets.

What are some family activities to do in Key West?

Families can enjoy a visit to the Key West Shipwreck Museum, engage with interactive exhibits at the Florida Keys Eco-Discovery Center, or have fun exploring the Key West Aquarium. A ride on the charming Conch Tour Train is also a delightful way to see the city.

What are some of the best day trip ideas in Key West?

For a memorable day trip, explore the natural beauty of Dry Tortugas National Park, which is accessible by ferry or seaplane. Also, consider a wildlife expedition at the Key West Wildlife Center, or learn more about the region's history with a visit to Fort East Martello Museum.

What types of vacation rentals are available in Key West?

Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Key West. From over 520 house rentals to over 410 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

Are there vacation rentals with a dedicated workspace in Key West?

Yes! Work meets play with ease at over 910 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.

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• › United States ›
• › Florida ›
• › Monroe County ›

Vacation rentals in Key West

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Bungalow in Key West

Atlantis House's Banyan Suite-voted top 25 in USA

About this space Atlantis House with just two exclusive rooms, the Master suite and the Garden suite, is the most private and romantic guesthouse in Key West. Rated a 2021 Travelers’ Choice Award by Trip Advisor. Perfect for Honeymoons and Anniversaries. A "little jewel" tucked away inside a lush tropical garden just steps away from the beaches. NOTE: Superhost Shari is a new owner of this property. Past reviews do not transfer but are 5-STAR! This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. Relax to island music on the Bose Mini Bluetooth speaker while you power up devices on provided chargers for countless photo op filled adventures that await! A corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee! Rejuvenate in the coveted in-room whirlpool bath with bubbles and soaking salts or cool off in the open shower with bench seating. The vanity is stocked with many toiletries and our white all-cotton bath robes allow for an extended spa experience. Please Note: The Banyan Suite is one of only two guest suites, separate from the Main Residence. The two suites have exclusive use of the lush backyard oasis with tropical trees, plenty of seating areas to enjoy the natural sounds of local wildlife or the pages of a good book. There is also a shared propane BBQ on the deck and an additional refrigerator with extra storage & ice located next to the complimentary cruiser bikes! The Banyan and Palm Suites each accommodate a maximum of 2 adults – Special accommodation for children may be included if the two guest suites are booked together. Guest access Guests have their own private entrance. Past reviews 5.0 out of 5 stars Cleanliness 5.0 Accuracy 5.0 Communication 5.0 Location 5.0 Check-in 5.0 Value 5.0

Nov. 23 – 30

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Aug. 4 – 11

Apartment in Key West

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Mar. 16 – 23

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Key West vacation rentals

Stay near key west's top sights, other great vacation rentals in key west.

Condo in Key West

Hidden Beach Duplex, Best Place in Key West

Houseboat in Key West

The Crystalmarine Suite – Rustic Luxury on the Sea

Guest suite in Key West

Conch Republic Studio - Key West Millionaires Row

Cottage in Key West

Mango Cottage 2 bedroom 2 bath with private pool

Jul. 9 – 16

Charming + Historic Eyebrow Home

Feb. 24 – Mar. 3

Home in Upper Sugarloaf Key

Bungalows at Sugarloaf Beach - The Lighthouse

Dec. 6 – 13

*Come to my Deck for a time you won't Forget!

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Gorgeous Romantic Private Villa, Steps from Duval!

Feb. 12 – 19

Southard Comfort ~ Feel The Key West Vibe

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Breezy pines 28 foot 5th wheel trailer .

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Oceanfront Condo in Key West

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Home in Marathon

The Gulf Cottage at Marathon Key

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Quick stats about vacation rentals in Key West

Destinations to explore.

• Varadero   Vacation rentals
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• Cottage rentals   Key West
• Rentals with a patio   Key West
• House rentals   Key West
• Rentals with an accessible height toilet   Key West
• Rentals with a hot tub   Key West
• Beachfront rentals   Key West
• Rentals with outdoor seating   Key West
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• › United States ›
• › Florida ›
• › Monroe County ›

Beachfront holiday rentals in Key West

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Key West

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

28 Dec – 4 Jan

Guest house in Key Largo

Guesthouse/Cabin peaceful romantic *sunsets beach.

Guesthouse/Cabin romantic *sunsets beach, docks and fishing pier, on a peaceful lush gardens with private parking to enjoy and relax, surrounded by nature wildlife at its best birds, iguanas, manatees, dolphin’s, eagles only a short walk to the beach and fishing pier, enjoy the immense boats cruising by, relax sipping cocktail. Note a "guesthouse" is part as on a state, small separate dwelling on the grounds of a larger one, used for accommodating guests. *the guesthouse is Not beachfront.

Cottage in Islamorada

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Holiday rentals for every style

Get the amount of space that is right for you

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Quick stats about beachfront rentals in Key West

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In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

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Home » North America » 15 STUNNING Airbnbs in Florida Keys [2024 Edition]

15 STUNNING Airbnbs in Florida Keys [2024 Edition]

The most southerly point of the United States, Florida Keys could be another country. One hundred islands made up of sandbars and mangroves welcome gently lapping turquoise waves onto their white sands. The flat, calm waters mean it’s the perfect place to go stand up paddle boarding or kayaking for lazy days hopping between the islands!

After a day of paddling or swimming, you’ll need somewhere to come back to. Why not take a look at vacation rentals in the Florida Keys? These can be anything from your own apartment in a condo to a yacht. They’re the perfect way to get a local feel for this stunning part of the world.

With that in mind, we’ve put together this list of the best Airbnbs in Florida Keys, curated by travel style, budget, and location. There are also some awesome Airbnb Experiences, so you can have a blast when you’re there. Let’s check it out!

Quick Answer: These are the Top 5 Airbnbs in Florida Keys

What to expect from airbnbs in florida keys, why stay in an airbnb, the top 15 airbnbs in florida keys, top 5 airbnb experiences in florida keys, final thoughts on florida keys airbnbs.

Bella Vita Condo steps from Duval

• > Two Guests
• > Wrap-around porch with chairs
• > Self-check-in

Unique Camping Shed near beach

• > Kayak campfire stargazing evenings

Romantic Retreat with private deck

• > Swimming pool and spa

Tropical family-friendly home

• > Eight Guests
• > Private patio
• > Heated pool

Multi-Million Beach Mansion with pool

• > $$$$$$$$$$$$$
• > Ten Guests
• > Private beach
• > Oceanfront heated pool

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From one of the best US National Parks , the Everglades to Key West, the most southwesterly point, it’s more than two hours by car (about 100 miles). So, location is important here.

With your own transport (maybe even get an RV rental?), the Keys are pretty easy to navigate, so it’s not the end of the world if you’re a little journey from your desired destination.

The next thing to take into consideration is cost. Florida Keys isn’t cheap; however, because Airbnbs offer great value for money, you can be assured that every dollar you spend goes towards a high-quality vacation rental, whether that’s a classy condo, a quirky tiny house, or a luxury yacht.

Many vacation rentals in Florida Keys are professionally managed through companies. However, you will find a few properties where you’ll be welcomed by a local host.

Florida Keys is a narrow strip of land surrounded by the sea. Since you’re never more than a few minutes from the water, why not stay on a boat? A boat could be anything from a small vintage sailboat to an ultra-luxurious mega yacht.

As with any type of property, what you get from your boat will depend on your budget. Smaller budgets get smaller boats, but if you’ve got a lot to spend, the sky is the limit. There are more than 100 boats listed on Airbnb in Florida Keys!

Boats that don’t have features like kitchens and dining areas will often be connected to a marina, where you can access hotel facilities such as restaurants, breakfasts, and gyms or swimming pools.

If you’re planning a group celebration, a villa is a great option. These large properties often have multiple bedrooms and living spaces indoor and out, so they’re ideal for families.

As well as a fully equipped kitchen, you can expect a swimming pool and a large garden – some may even have their own private beaches, though you will pay a premium for those. Many villas in Florida Keys are part of resorts, so you’ll have access to amenities in those too.

Though they may seem expensive at first glance, because these are large properties, it’s easy to split the cost between guests. A villa might actually be the most cost-effective way of travelling if your group is bigger than four. Imagine that!

Condos (or condominiums) are like apartments, but a little different. If you’re from the United States, they’ll need no further explaining. You may even live in one! However, for travellers from the rest of the world, they’re a large building where you own or rent the living area of your building but share common areas.

Condos are great for vacation rentals because common areas often include things like gyms, swimming pools, and roof terraces – perfect for soaking up the Floridian sun! Though you can get large condos, these are usually suited to smaller groups of less than four people. Couples will love them!

There’s no search function specifically for condos on Airbnb. However, if you search entire flat or private room, the listing title often will include condo.

If you’re still not sure you should choose a vacation rental over a hotel, let us give you five of the top reasons to stay in an awesome Florida Airbnb .

• Local Experience: With a local person or business acting as your host, you can get lots of recommendations on the best things to do that you won’t find in the guidebook.
• Privacy: Lots of Airbnbs have self-check-in. You can even filter for completely private accommodation if you want to!
• Affordability: In a pricey area like Florida Keys, value for money is important. Luckily, Airbnbs usually offer more for your money than hotels of an equivalent price. That doesn’t just go for the Florida Keys, but for all travel destinations in the USA .
• Safety: Staying in someone else’s home may seem like a risk, but that risk is heavily reduced with Airbnb’s vetting system. Customer Support is on hand 24/7 too!
• Airbnb Experiences: It’s not just about places to stay; Airbnb Experiences helps you to get acquainted with your destination. More on that later!

Now you know what to expect and why you should choose vacation rentals, let’s get to the part you’ve all been waiting for. Here are 15 of the coolest Airbnbs in Florida Keys. You’re going to love them!

Overall Best Value Airbnb in Florida Keys | Bella Vita Condo steps from Duval

• Wrap-around porch with chairs
• Self-check-in

Ideal for couples, this colourful property is a great value Airbnb in Key West. It’s less than half a block from Duval Street, and many other landmarks are within a stone’s throw. Back in the flat, you’ll be treated to bright decor, a king bed, flat-screen smart TVs, and a cosy living area. Enjoy your morning coffee on the porch and watch the world go by!

This spot has one of the best locations in Florida Keys – just half a block from Duval Street! The king bed makes it perfect for couples, who can spend the morning enjoying a coffee and people-watching from the porch.

Best Budget Airbnb in Florida Keys | Unique Camping Shed near beach

• Kayak campfire stargazing evenings

The Florida Keys are a lot of things, but cheap isn’t one of them . However, with some research, you can find affordable properties, such as this tiny house in Key Largo. Offering a glamping experience, there’s a king bed in the hut and a small outdoor space. Your host offers kayak campfire stargazing experiences too, so get in touch with them if you’d like to know more.

Perfect Airbnb for Solo Travellers | Key West Cozy Home

• Awesome location
• Kayaks and paddle boards for rent

Home stays are a great option for solo travellers. They not only allow you to save some cash, but also to have a completely local experience during your stay. At this family home on Stock Island (near Key West), there are kayaks and paddleboards for rent, and you’re welcome to use the communal areas of the house. Did we mention the home is right on the water?!

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Best Short Term Rental for Couples | Romantic Retreat with private deck

• Swimming pool and spa

This cute, free-standing cottage dates back to the 1800s and is the perfect romantic Airbnb for a couple. Not only does it have a king bed inside, but there’s a rocking love seat on the private deck as well as a table and chairs – and a private hot tub! There are also heated swimming pools on the property that you’re welcome to use.

Best Airbnb in Florida Keys for Families | Tropical family-friendly home

• Private patio
• Eight Guests
• Heated pool

Another property close to Duval Street in Key West, this Airbnb is perfect for families. There’s room for up to eight guests across three bedrooms, with singles and sofas in the smaller room perfect for children. With a fully equipped kitchen, you can save a few dollars over eating out, and there’s free parking on the driveway, too. You can even bring your furry friend as pets are welcome!

Over the Top Luxury Airbnb in Florida Keys | Multi-Million Beach Mansion with pool

• $$$$$$$$$$$$$
• Private beach
• Oceanfront heated pool

This place is just insane. You have your own private beach overlooking Summerland Key! Not only that, there’s a heated pool right by the ocean, a pool table, and a hammock. This place is perfectly set up for you to chill out and escape the real world. There’s space for up to ten guests, so it’s good for families and friends. We’re sure you’ll spend all your time outside, but it’s good to know there’s a 56-inch curved TV waiting for you in the living room.

Best Boat in Florida Keys | Floating Tiny House – 70’s sailboat

• Access to hotel facilities
• Retro design

This renovated 25-foot sailboat hails from 1978 and is packed with retro charm. It’s docked in Stock Island marina, so as well as your cute boat, you’ve got access to the Perry Hotel. Here, there’s a bar, gym, restaurants, pools, and even dog parks! The boat, named Poppy, is quite small. It’s ideally suited to a solo traveller, or it could be a romantic retreat for a couple.

Best Villa in Florida Keys | Four bedroom villa on Duck Key

• Swimming pool
• 35-foot dock

Duck Key is about halfway down Florida Keys, and there are some pretty awesome villas here – such as this one. Another property ideal for families, four bedrooms can sleep up to ten guests, there’s a fully equipped kitchen and a swimming pool. As well as free parking, you can take advantage of a 35-foot dock to moor a boat.

Best Condo in Florida Keys | Affordable Beachfront Luxury sleeps six

• Olympic swimming pool
• Covered picnic areas and grills

Back in Key West, you’ll find this cool condo close to Smather’s Beach. The large indoor space boasts a kitchen, sitting area, and three bedrooms, but it’s the shared spaces that make this place special. You’ve got access to an Olympic sized swimming pool and hot tub right by the beach! Prefer to stay dry? Make use of the grilling area and covered picnic areas and enjoy some lunch. Go on, treat yourself!

Perfect Airbnb for Digital Nomads | Mallory House Room

• Dedicated workspace
• Close to cafes and restaurants

Being a digital nomad is becoming more and more common. All you need is a laptop, somewhere to work, and fast Wi-Fi. If you supply the laptop, Mallory House will give you the other two ingredients. This boutique hotel is close to the cafes of Key West, so if you fancy a change of scenery for the day, it’s easy to get one. When you’re chilling at the guest house, be sure to take your hosts up on their offer of a complimentary coffee overlooking Duval Street.

Most Unique Airbnb in Florida Keys | Stars and Stripes Lifeguard Tower

• Waterfront location
• Breakfast included

Always dreamed of appearing in Baywatch? That may never happen, but you can pretend when you’re staying in this lifeguard tower! Located at the very north of the Keys in Key Largo, it offers easy access to the Everglades too. Breakfast is included in this no-frills accommodation, and it’s sure to make memories that last far beyond your flight (or drive) home.

Best Airbnb in Key West | Casa Loca

• Private heated pool
• Concierge service

A lot of the Airbnbs we’ve seen so far are in Key West, and that’s no surprise; it’s the most popular location in the Keys! It’s probably got the biggest selection of accommodation, but here’s one more we think you’ll love. Boasting a private heated pool and concierge service, this luxurious retreat is ideal for a family or group of friends. It’s usually booked, so move fast!

Best Airbnb in Islamorada | Two bedroom condo for four

• Self check in
• Ocean views

Islamorada and Tavernier are closer to the north end of the Keys, and they’re much quieter than Key West. For some, that might be a big attraction. This condo has room for four guests across two rooms, so it could suit a small group or a couple. You have access to a cafe, a large heated pool, and spectacular ocean views from here.

Best Airbnb in Key Largo | Charming Key Largo Cottage

• Paddle boards and kayaks

Another Key Largo Airbnb, this cute cottage is right on the water and comes with kayaks and paddleboards. The tiny house cleverly uses space to make room for up to four guests in a studio style room in an RV park. The cottage has a fully equipped kitchen stocked with a coffee maker and other useful appliances.

Best Airbnb in Marathon | Fully furnished efficiency studio

• Shared pool
• Fully equipped kitchen

Last but not least is this small cottage by the ocean in Marathon. It’s great for solo travellers or couples on a budget. The studio-style apartment comes with a fully equipped kitchen, queen bed, and an open plan living space. Outside, you can chill out at the picnic table and enjoy a meal under the stars in the evening!

Hopefully, you’ve found somewhere you want to stay. While you’re mulling it over, let’s take a look at Airbnb Experiences. These are tours and trips curated by native Floridians (mostly), and they’re a cool way to travel like a local in your destination.

Airbnb Experiences in Florida Keys can be anything from snorkelling with dolphins or sailing on historic yachts to super fun booze cruises. It all depends on your tastes.

With more than 20 Airbnb Experiences in Florida Keys to choose from, you certainly won’t be bored during your stay. Here are five of our favourites!

Biologist Guided, Dolphins and Snorkel

• $117/person
• Up to 8 Guests

The Florida Keys are packed with wildlife, and this is the ideal opportunity to get up close and personal with it. You’ll set sail on a catamaran to an area that is home to roughly 200 Bottlenose dolphins. You’ll remain a safe distance away as you admire these beautiful creatures. Then, it’s onto a snorkelling spot where you’ll uncover sponges and tropical fish. Fresh fruit and drinks are provided as part of the trip.

Mallory Glow Tour

• Up to 6 Guests

Here’s one if you’re staying in Key West. There are a whole host of watercraft that make exploring the waters of the Keys a treat – including stand up paddleboards and kayaks. However, on this Airbnb Experience, you’ll be pedalling a water bike! It’s a fun activity for all ages, and a sunset you’ll remember for a lifetime. Once it gets dark, you can walk to performances in Mallory Square or listen to Sunset Pier’s music from your ‘bike.’

Sunset Sail on Historic Schooner Yacht

• Up to 10 Guests

Want to explore the Keys and experience a slice of history? This classic schooner will provide that. You’ll leave Key West’s historic seaport for a two-hour sunset experience, and there’s complimentary wine and beer on board. Sit back, relax, and enjoy the views as the Schooner navigates the calm waters. Once you’re back on land, you’ll feel like a new person!

Historic Seaport Food and Walking Tour

In an area surrounded by so much water, that means one thing when it comes to the cuisine – seafood! On this tour, you’ll be trying fresh fish tacos, lobster mac ‘n’ cheese and pink shrimp. And of course, a slice of world-famous Key Lime Pie, which was invented just up the road in Key Largo! This three-hour tour is a must for foodies in Key West.

Ultimate Party Boat Cruise in Key West

Jump on your pedal-powered party boat and launch from Key West to enjoy the views and some drinks. It’s BYOB, but your hosts have taken care of everything else – including music, party lights, ice, and coolers. We’d suggest doing this at sunset, when you’ll enjoy 2.5 hours of the most stunning vistas with your drinks.

Don’t Forget Your Florida Keys Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

So, there you have it. Those are the 15 best Airbnbs in Florida Keys, with some really cool Airbnb Experiences thrown in too. Whether you want to stay in a tropical villa with a pool, a cool condo, or even a tiny house lifeguard tower, there’s an Airbnb in Florida Keys for you.

Still can’t make your mind up? Well, let us round off with reminding you of our overall best value Airbnb in Florida Keys. That’s the Bella Vita Condo steps from Duva l. Located just steps from the Key West Historic District, it has awesome reviews, and you’re sure to love it.

We hope that wherever you choose to stay in Florida Keys, you have a fantastic vacation. To keep yourself and your belongings safe, make sure you check out World Nomads for travel insurance!

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Colleen Kinsey

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Vacation rentals in Key West

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Top-rated vacation rentals in Key West

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Bungalow in Key West

Atlantis House's Banyan Suite-voted top 25 in USA

About this space Atlantis House with just two exclusive rooms, the Master suite and the Garden suite, is the most private and romantic guesthouse in Key West. Rated a 2021 Travelers’ Choice Award by Trip Advisor. Perfect for Honeymoons and Anniversaries. A "little jewel" tucked away inside a lush tropical garden just steps away from the beaches. NOTE: Superhost Shari is a new owner of this property. Past reviews do not transfer but are 5-STAR! This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. Relax to island music on the Bose Mini Bluetooth speaker while you power up devices on provided chargers for countless photo op filled adventures that await! A corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee! Rejuvenate in the coveted in-room whirlpool bath with bubbles and soaking salts or cool off in the open shower with bench seating. The vanity is stocked with many toiletries and our white all-cotton bath robes allow for an extended spa experience. Please Note: The Banyan Suite is one of only two guest suites, separate from the Main Residence. The two suites have exclusive use of the lush backyard oasis with tropical trees, plenty of seating areas to enjoy the natural sounds of local wildlife or the pages of a good book. There is also a shared propane BBQ on the deck and an additional refrigerator with extra storage & ice located next to the complimentary cruiser bikes! The Banyan and Palm Suites each accommodate a maximum of 2 adults – Special accommodation for children may be included if the two guest suites are booked together. Guest access Guests have their own private entrance. Past reviews 5.0 out of 5 stars Cleanliness 5.0 Accuracy 5.0 Communication 5.0 Location 5.0 Check-in 5.0 Value 5.0

Nov 23 – 30

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Apartment in Key West

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Mar 16 – 23

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Key West vacation rentals

Stay near key west's top sights, houses in key west.

Home in Key Largo

Your Keys Getaway!

Jan 25 – Feb 1

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Oceanfront Tiny Villa in the Heart of the FL Keys

Sep 16 – 23

Beachfront Villa - Florida Keys

Home in Cudjoe Key

Paradise and Cudjoe Bay

Sunrise Beach Escape

Jun 25 – Jul 2

Cudjoe Key Home with a View

Marathon one-level home on the Marina - with slip!

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Jan 22 – 29

Waterfront Sunsets, Great Price, Relaxing Spot!!!

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Flakey's

Aug 17 – 24

The Gulf Cottage at Marathon Key

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

Condos in Key West

Condo in Key Colony Beach

Key Colony Beach Luxury Condo, New Modern Interior

Condo in Key West

Large waterfront 2/2 end unit with boat slip

Beachside Unit 28 - Private Beach, Pool & Paradise

Anchor Drop modern elegance upgrades throughout vi

Aug 11 – 18

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Condo in Marathon

Sombrero Beach Tropical Getaway

Condo in Tavernier

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Jul 30 – Aug 6

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Aug 22 – 29

Best View Ocean Pointe Pool Beach King Bed, Gated

It's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba

Condo in Key Largo

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

Feb 16 – 23

Tropical Getaway

Aug 23 – 30

Lake houses in Key West

Waterview from three sides, Cabana Club, 30' Docks

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

NEW CASA PALMA VOTED BEST AIRBNB RENTAL! GOLF CART

Sep 13 – 20

Waterfront Escape -VACA-23-408

Apr 25 – May 2

Venture Out -Million Dollar Island Resort

Walk to Sombrero Beach, 50’Dock, SPA, Bikes,Kayaks

5 O'clock Somewhere - Key Largo

Apr 30 – May 7

Waterfront Key Largo Home - Tropical Paradise

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

5 O'Clock Somewhere Bay House, Drinks on Us!

Dec 16 – 23

Marathon Beach house w/45’ dock Ocean access

Tropical Waterfront, Boat Dock, Sunset View, Kayak

Jun 28 – Jul 5

Quick stats about vacation rentals in Key West

Your guide to key west, all about key west.

Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.

Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.

The best time to stay in a vacation rental in Key West

Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.

Top things to do in Key West

Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.

Ghost tours

Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.

Key lime pie

Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.

Frequently Asked Questions

How is the weather in key west.

Key West has a tropical climate with warm temperatures year-round. Summers, from June to August, can be hot and humid, often reaching 90°F (32°C). Winters, from December to February, are milder, with temperatures typically around 70°F (21°C), and less rainfall.

What are some of the best things to do in Key West?

Popular activities in Key West include exploring the vibrant coral reefs on a snorkeling trip, discovering local marine life at the Key West Aquarium, or visiting the historic Fort Zachary Taylor State Park. A stroll along Duval Street for shopping and local cuisine is also recommended.

What is the best time of year to visit Key West?

Key West is particularly lively between March and May, with milder temperatures and fewer crowds. During these months, you can enjoy events like the Conch Republic Independence Festival and the Key West Songwriters Festival.

What are the best places to stay in Key West?

Some highly-rated areas to stay in Key West include Old Town, a historic district with classic architecture, Truman Annex for its peaceful atmosphere, and New Town for its modern conveniences. Duval Street is also favored for its proximity to dining and shopping options.

What are the best places to visit in Key West?

Key West is known for diverse attractions such as the Ernest Hemingway Home and Museum, where the renowned author once lived, and the Key West Butterfly and Nature Conservatory. Don't miss the stunning sunsets at Mallory Square, and the view from the historic Key West Lighthouse. The Southernmost Point Buoy is also frequently visited.

What are some hiking trails in Key West?

While Key West is not known for its hiking, you can enjoy a leisurely walk at the Key West Tropical Forest and Botanical Garden. The Island City National Historic District also has interesting paths through the town's picturesque streets.

What are some family activities to do in Key West?

Families can enjoy a visit to the Key West Shipwreck Museum, engage with interactive exhibits at the Florida Keys Eco-Discovery Center, or have fun exploring the Key West Aquarium. A ride on the charming Conch Tour Train is also a delightful way to see the city.

What are some of the best day trip ideas in Key West?

For a memorable day trip, explore the natural beauty of Dry Tortugas National Park, which is accessible by ferry or seaplane. Also, consider a wildlife expedition at the Key West Wildlife Center, or learn more about the region's history with a visit to Fort East Martello Museum.

What types of vacation rentals are available in Key West?

Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Key West. From over 520 house rentals to over 410 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

Are there vacation rentals with a dedicated workspace in Key West?

Yes! Work meets play with ease at over 910 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.

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The Most Stunning Airbnbs In Key West

Key West, Florida , boasts beautiful turquoise waters, abundant marine life, and of course, the best key lime pie in the world! According to Key West's tourism website , you must take the famous Overseas Highway to access this idyllic island in the Atlantic. Whether you're looking to shop, swim, or simply eat and drink your way through this dynamic and fun vacation spot, Key West truly has it all.

If you're a lover of literature, you'll also be fascinated by Ernest Hemmingway's impact on the island, as well as his legendary six-toed cats that roam freely. However, no matter what you want to focus on during your time on the island, catching one of its superb sunsets is an absolute must. While there are some high-end resorts that you can stay at, Airbnb makes it easy to find some of the best local accommodations as well as the cutest bed and breakfasts. That being said, we've rounded up some of the most stunning Airbnbs in Key West!

1. Stay right on the ocean at this gorgeous studio

Between the private beach and the crystal clear ocean views, this quaint studio is perfect for two people seeking a beach-side getaway. According to the Airbnb listing , this rental is only a five-minute walk to Duval Street, home to some of the best bars, eateries, and nightlife in Key West. Despite being so close to the more exciting side of the island, this timeshare offers a quiet and peaceful retreat, making it easy to have the best of both worlds during your time in the Florida Keys.

In addition to the private beach that sits right outside your front door, there is also a pool and hot tub for guests to use. Soak under the stars while appreciating the sea breeze in the evenings, or start your day off with a refreshing dip in the pool to get you going. Though the interior is very beachy and bright, the best spot in the house is definitely on the balcony. Watch the waves roll in as you sip your morning coffee in bliss.

2. Check out this modern rental in Old Town Key West

Per Airbnb , this bright and airy one-bedroom unit is just one block away from the hustle and bustle of Duval Street. Between the warm wood finishes throughout the space and the bright and clean tile backsplash in the kitchen, this rental invites you to unwind and get cozy in the heart of Old Town. When it comes to design and decor, there is a real sense of professionalism that can be seen in each room. From the high-quality furniture to artistic highlights like the bird sculpture behind the master bed and the bamboo wall in the backyard, this rental has a cohesive style that does not go unnoticed.

No matter what room of the house you're in, there is a stylish sense of cohesion that invites you in and encourages you to slow down. There are also a couple of seating areas in the backyard where you can gather with friends or family over a glass of wine in the evenings or coffee in the morning. If you choose to stay in and cook a meal at home, eat outside on the patio to catch the sunset.

3. A pink two-bedroom in downtown

Located in downtown Key West, the Wyland Penthouse boasts spacious accommodations that are both sophisticated and stylish. According to the listing on Airbnb , this two-bedroom penthouse sits right above the Wyland Galleries on Duval Street, meaning that delicious food and fun bars are right outside your front door. The pink exterior of the Wyland Galleries makes it impossible to miss while strolling down the street. Between the high ceilings and the classic French doors, this rental truly transports you to a tropical yet elegant atmosphere.

When you're ready to do some people-watching, head out to the patio area and look out onto the busy Duval Street for a stimulating scene. While the house's interior has some great places to sit down for a drink or tasty meal, none are better than the dining table on the patio. Surround yourself with the pink walls of the building as you sit under a sea of string lights and watch the sky dance as it turns from day to night.

4. Enjoy a secluded stay at Casa Cristol

According to the Airbnb listing , Casa Cristol is situated in a gated community, giving you optimal privacy, seclusion, and safety. Whether you want to start your day with a cup of coffee in the living room as the morning light pours in through the French doors, or you prefer to walk to a cafe on Duval Street, the world is your oyster while staying at Casa Cristol. Upon arriving, guests are greeted with an idyllic, white picket fence and lush, green palm leaves surrounding the property.

Between the in-house washer and dryer and the full kitchen, guests seriously have everything they need to feel right at home during their stay. Some other amazing amenities at Casa Cristol include a shared swimming pool, a picturesque balcony, and a nice outdoor dining area immersed in a vibrant green garden. Since this home can host up to six guests at a time, it is the perfect spot for a small group or family looking to live it up in the Keys!

5. Spend the night in the middle of the ocean in a Tiki Suite

Perhaps the most unique rental on our list, the Grand Tiki Suite offers a romantic experience out on the open sea for two people. Per the Airbnb listing , the Grand Tiki Suite has everything from a king-sized bed to a TV to a mini-fridge. Literally wake up to the sunrise reflecting off of the surrounding ocean, or lounge in the hammock on the small patio of the floating hut. Though it is certainly an unconventional accommodation, the hardwood flooring and outdoor deck provide a sense of stability even when floating around the Atlantic.

While the Grand Tiki Suite is an optimal spot for relaxation and restoration, it also gives you easy access to all of your favorite water sports and activities. Guests of the suite will find that their rental comes with two inflatable paddleboards and two sets of snorkel gear, meaning you can hop in the water and get started at your leisure.

6. Stay on a luxury boat

According to Airbnb , this houseboat is anchored one mile away from the shore so that guests can experience what it is like to sleep under the stars ... in the middle of the ocean! This sizable boat can fit four guests at a time, making it a great option for a small group traveling to the Keys. Though you will have to take a boat taxi to and from your unique rental, it is only $15 per ride. That being said, you'll probably want to map out your time beforehand so that you don't have to take multiple boat taxis a day. You'll also want to plan around the captain's schedule.

If you are looking to unplug more than usual on your trip, you'll be pleased to learn that the boat is solar-powered, meaning that electricity is limited. Immerse yourself in a refreshing sense of seclusion as you take in the sunrise and sunset each morning, watching the sun reflect off of the turquoise waters. All in all, this boat is a great option for adventure-seekers and spontaneous travelers!

7. Kick back at this adorable cottage

Located within the Paradise Inn, this rental boasts an adorable and charming stay. Per the listing , this cottage can accommodate up to six people at a time across two very airy and bright bedrooms. For the most part, the cottage's interior has a lot of white and neutral colors, setting the scene for a relaxing and mellow island vacation. Best of all, staying at this Airbnb means that you get to experience a free happy hour and breakfast provided by Paradise Inn! Enjoy the complimentary happy hour in the bar every day from 5:00 pm to 7:00 pm, along with a complimentary continental breakfast from 8:00 am to 10:00 am.

In addition to the two bedrooms, two more people can sleep on the plush sofa bed in the living room. Once you are ready to do some exploring, simply walk down the street to everything you could need or want to see in Key West. There is also a shared pool in the back, meaning you can easily stretch out and catch some sun during a mellow day.

8. Walk to the beach from this cool condo

According to the Airbnb listing , this rental is within walking distance of everything from Mallory Square to Hemingway's Home. Are you looking to have a nature-packed trip? Head over to Zachary Taylor Park for some of the island's best snorkeling and swimming. You can also do yoga or swing in a hammock under the blazing Florida sun. This condo's colorful and unique interior really boosts your mood and gets you in the sunny spirit.

From lounging on the deck in one of the navy recliners to enjoying an energizing meal at the breakfast nook, this rental encourages guests to put their feet up and indulge in the island life. The curved staircase is also a real treat for architect-lovers. Enjoy a dip in the shared swimming pool or walk down to the beach for some sea-shell hunting. Whatever you do, just be sure to get outside and soak up the sun!

9. Stay at a colorful cottage

The Royal Poinciana Cottage can be recognized by the vibrant mint green exterior and classic white picket fence, per Airbnb . Since it only has one bedroom, this rental is best suited for couples or solo travelers seeking a peaceful getaway in the Keys. In addition to the queen bed, this cottage also has a full kitchen, bathroom, and outdoor dining area. Though the design and decor of the space aren't much to write home about, the outdoor deck and garden are the real highlights of this rental.

The modern pool deck is perfect for catching some rays and deepening your tan during the daytime. It is also a great length and size for swimming laps to get in some easy exercise. There are also a few outdoor dining tables for you to use. Whether you want to host a little dinner outside or simply sip on a tropical rum cocktail under the stars, the world is your oyster while exploring Key West!

10. Stay three blocks from the beach in this vibrant condo

Per Airbnb , La Dolce Vita is a unique condo that has a snazzy aesthetic and is situated in the heart of Old Town. Choose between taking a stroll to the coolest cafes, shops, and restaurants or walking three blocks to white, sandy beaches. While the yellow and red interior might be a bit overwhelming for some, it certainly creates a unique and swanky scene. The space is also elevated by lime green lights surrounding the bottoms of cabinets and corners in the kitchen, giving the rental a somewhat futuristic look.

If you find yourself in need of some fresh air but don't feel like getting your feet sandy at the beach, step onto the front deck and take a seat on the white lounge chairs. Catch the refreshing breeze while catching up on emails or enjoying a nightcap in the evenings. There is also a shared swimming pool for those who prefer the comfort of a more predictable body of water than the ocean.

11. Live the island life at this cozy cottage

According to the listing on Airbnb , this dog-friendly cottage is perfect for those who want to travel with their four-legged family members! Between the king-sized bed in the main bedroom and the spacious sofa bed in the living area, this rental can house up to four guests at a time. Since it is located in a very residential area, the evenings tend to be fairly quiet and peaceful. However, if you're looking for a more wild time, walk over to Duval Street and have a drink or do some dancing!

The simple yet cozy interior features plush couches, beachy accents, and a luxurious full bathroom. Take a stroll through the shared gardens with coffee or tea to indulge in a peaceful morning or cool off in the small shared swimming pool in the back. Though you can't swim laps in the pool, it is perfect for sheltering yourself from the blazing Floridian heat. Since the outdoor areas are shared, this is a great rental for people looking to mingle and make new friends along the way.

12. Enjoy a private room at the Curry Mansion Inn

The Curry Mansion Inn is a very classic and elegant accommodation in the heart of Key West. According to the Airbnb listing , this quaint room in the Curry Mansion Inn has a plush bed and private bathroom, giving you a sense of privacy while staying in a shared space. Each room also contains a TV with cable, a mini-fridge, and antique touches throughout. Since there are only 28 rooms within the Curry Mansion Inn, guests can expect top-notch service and comforting attention to detail.

When it comes to the shared amenities, guests will find some unique spaces like the lush garden and the charming library. There is even a business center if you need to take care of some work while there. Of course, in true Key West fashion, no tropical Inn would be complete without a crystal blue swimming pool and hot tub, ensuring that you spend as much time outdoors as possible.

13. Stay on the Miss Bandit yacht for a unique experience

According to the listing on Airbnb , the Miss Bandit yacht can host up to four guests at a time. This 53-foot houseboat allows you to live comfortably while out at sea, creating a one-of-a-kind lodging experience. With a cozy-cabin feel, Miss Bandit features wood-paneled walls with vintage Burt Reynolds photographs that transport you back in time to the '70s or '80s. Compared to most other boats, the kitchen, living area, and bedroom are all pretty spacious and open.

Guests will also find that the shower is actually huge for a boat, making it easy to feel comfortable and at ease while living in a more unconventional space. Since the boat is moored at the Stock Island Marina, guests can use the pool and fitness center there, ensuring you won't feel claustrophobic or cramped on the boat. There are also some great restaurants, bars, and shops at the marina that you'll definitely want to check out!

14 docked boats you can book on Airbnb including the original 'Caddyshack' yacht

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• You don't necessarily need sailing skills to spend a night on the water.
• Houseboats across the US may be rented on Airbnb and make for a truly unique stay.
• We found Airbnb boats across the country ranging from $114 to $436 per night.

There's nothing quite like an escape on the water — and we're not talking about a lakeside cabin .

Rather, sleeping on the water, in the form of an Airbnb houseboat rental, can be a rejuvenating retreat. They make for a socially distanced escape too, since they function as your own private, floating residence in the middle of a body of water. 

Spending a night on a yacht or sailboat is also more unique than booking a traditional hotel or vacation rental, and you can find all kinds of boats on Airbnb across the US. From the lakes of Wisconsin to California's bays, climb aboard parked vessels of all sorts, with no sailing skills required.

Browse all of the best boats on Airbnb below, or jump to a specific section:

• The best Airbnb boat rentals
• FAQs: Houseboat rentals
• More great unique Airbnbs

These are some of the best boat Airbnbs in the US, sorted by price from low to high.

Fully equipped 52' houseboat in kemah, texas.

Book this Texas boat on Airbnb

Stay on a 52-foot remodeled houseboat that's docked in a peaceful marina. It's located in a natural bird sanctuary so you can hear the calls of the birds from the boat's three main decks.

The interiors are relaxing and feature a marble shower, two flat screen TVs, and a spot for evening cocktails on a deck with a patio table, chairs, and shade awnings. 

There's a private man-made "island" shared between your rental and seven others owned by the same Superhost that acts as a barbecue and recreation spot. Staying here includes a gas barbecue and shrimp boiler, a pergola with a ceiling fan to hang out in, and canoes and kayaks you can take out for a paddle.

Charming sailboat in Racine, Wisconsin

Book this Wisconsin boat on Airbnb

Located on expansive Lake Michigan, this Airbnb boat rental has tight quarters (you'll be sleeping across from the kitchen sink), but the space still feels bright and airy. 

There's a cute blue Smeg fridge, a cozy dining nook, and a deck with plenty of seating and a handy charcuterie board set-up for sundowner cocktails.

Relax onboard playing cards or head onshore to the marina for the hot tubs, heated pool, or restaurant, which are all included as part of your reservation.

There aren't showers, but there is a toilet, and showers at the marina are easily accessible and clean. While the boat does sleep three, the stay is most ideal for couples.  

Desert houseboat with pool in Joshua Tree, California

Book this Joshua Tree boat on Airbnb

Moored in the Joshua Tree Land Yacht Club and located on dry land in the desert expanse of Joshua Tree, California, this boat is exceedingly unique.

You'll sleep on a colorful Queen bed in the bow of the boat with blackout blinds to fend off the bright light of the desert. There are two chairs on the deck for enjoying a morning cup of coffee, and right outside is a stargazing deck for spotting constellations and meteor showers. Best of all, there's a stock tank pool for cooling off.

Though the boat is all yours for the duration of your desert voyage, an outdoor "surfboard shower," nautical outhouse, a fire pit, a kitchenette, and a grill are shared amenities with artists who live on-site.

Modern and elegant houseboat in Stuart, Florida

Book this Florida boat on Airbnb

This houseboat could easily double for a cheerful, nautically-themed apartment given the spacious layout and maritime touches, such as a turquoise sofa and twin armchairs are adorned with fish-print pillows.

The subway-tiled kitchen offers much more room than you might expect and the sunny bathroom has a shower. The bedroom includes a Full-sized bed and sliding glass doors that lead to a deck with lounge chairs. 

You'll be docked within a pleasant marina that's a five-minute walk from downtown boutiques, restaurants, and coffee shops. The host also provides bikes if you want to explore excellent beaches just six miles away. 

Unique concrete houseboat in Sanford, Florida

Concrete, but make it float. It might sound surprising, but this perfectly seaworthy boat was made from concrete in Sweden in 1973 and did two full laps around the globe before becoming the cool floating getaway it is now.

Decorated in slate gray, charcoal, sand, and turquoise hues, the space offers a calming, modern take on small interiors. There are cozy seating nooks, a narrow but long kitchen, a separate bedroom with a Queen-sized bed, and a sleek tiled shower in the compact bathroom. 

The surrounding marina offers additional showers, restrooms, laundry, a diner, and a restaurant and bar with a pool. Downtown Sanford is also close by.

Motor yacht in New Bern, North Carolina

Book this North Carolina boat on Airbnb

This motor yacht offers all the comforts of an ordinary home with cushioned furniture, television, plush carpeted floors, and more. Even better, you'll wake up to beautiful views of the Neuse and Trent Rivers from the roomy cabin that includes nautical and bright blue decor.

Climb up to the sundeck with lounge chairs and a daybed for viewing spectacular sunsets. 

Although two guests are allowed, there is a capacity for four guests with the use of a sofa bed at an additional charge of $50 per person.

The yacht is parked in a convenient location adjacent to the historic downtown area filled with restaurants, shops, and bars.

Harbor yacht in Boston, Massachusetts

Book this Boston boat on Airbnb

Boston is known for its classic brownstones that date back to the founding of the city, and this posh yacht is docked near it all. The historic Bunker Hill monument, the USS Constitution Museum, and Boston's oldest neighborhood, the North End, are all within walking distance.  

Pretty water views and cool water breezes are found throughout the boat, and glossy teak finishes and white leather complement red and blue accents for a strong nautical theme.

There are two staterooms, each with its own baths, and a small kitchen and a living area. The compact kitchen doesn't permit the use of the cooktop, but there is a coffeemaker, toaster, microwave, and convection oven. 

From November to April 1st, the boat is wrapped in shrink wrap to block snow and keep the interior warm, and while it might not look as photogenic, you can still plan an offseason stay.

Marina resort boat in Key West, Florida

Book this Key West boat on Airbnb  

If you're heading to gorgeous Key West, this boat rental is a great way to experience the water and wildlife up close. Lucky guests may even spot manatees and dolphins from the deck.

The interior of the boat features teak furnishings, polished brass accents, and nautical blue hues. Two beds include a Queen-sized V-berth bed in the main stateroom and a half-berth bed off the main cabin.

Operated by an Airbnb Superhost, this hand-built sailboat is docked within the Perry Hotel's resort marina. As such, boat guests have access to the amenities of the high-end resort, too, including a pool, fitness center, and a free shuttle that takes guests from the marina to downtown Key West. 

While there's a toilet and sink on board, showers are at the marina. Similarly, there's an in-counter fridge and Keurig, but no microwave or stove.

Modern Houseboat on a pond in Bremen, Maine

Book this Maine boat on Airbnb

This gorgeous houseboat floating on a pond evokes the simple feel of a tiny home. The wooden panels and light-filled space provide an airy feel and there is both a double bed and a single bed in the main cabin. All cooking and essentials such as linens, soap, fresh drinking water, and life jackets are included as well.  

While the inside is inviting, save time to sunbathe on the outdoor and upper sun decks for great views and prime lounging. Although the boat is stationed on the water, a canoe is included for the guests to travel onshore. 

Private boat charters may also be arranged with the host. Keep in mind that guests are not allowed to drive or operate the boat themselves and the boat will remain parked for the duration of the stay.

Vintage boat in Gig Harbor, Washington

Book this Washington boat on Airbnb

If you're looking for a vintage stay, this restored historic Airbnb is less than an hour from Seattle and infused with character and charm.

The kitchen is adorned with brass lanterns, while a comfortable dining nook has a seafoam green bench and lace trim. There are also two bathrooms on board, a rarity for boats, including one with brass portholes and one tucked away under a folding ceiling panel.

Bedrooms are small but comfortable, with white linens and portholes to keep the vibe breezy and light. The host also includes two kayaks for guests to use as well as a barbecue on the dock.

Houseboat hotel in Douglas, Michigan

Book this Michigan boat on Airbnb

This 43-foot houseboat, or "floating hotel," as the host describes her, has everything guests need for a relaxing weekend escape.

A good size bedroom offers a Queen-size bed so you won't have to sleep in any tight spaces, and the interior is sleek and modern with updated black cabinetry, a fully stocked kitchen, and a pullout sofa.

Outside, guests have full access to marina and wharf facilities, which include grills, showers, a pool, additional bathrooms, a gazebo, and laundry.

The original 'Caddyshack' yacht in Stevensville, Maryland

Book this Caddyshack yacht on Airbnb

Cinephiles will appreciate the chance to stay on the actual yacht from the 1980 Bill Murray comedy "Caddyshack."

The well-maintained boat is outfitted to host a dedicated crew of fans, thanks to three bedrooms and three full bathrooms spread across the boat's 60-foot length.

Bench seating wraps around the deck and the kitchen is large enough for entertaining a crowd. Of course, there are also nods to its cinematic history. You'll be able to hear the iconic horn Rodney Dangerfield played in the movie, and there are autographed photos of Dangerfield and stills from the film.  

While the boat is rented with the understanding it'll stay put in its berth, guests may talk to the Superhost about chartering a cruise on the Chesapeake Bay. Fishing trips can be booked in the marina as well. 

Spacious 84' yacht in South Pasadena, Florida

Book this Florida yacht on Airbnb

If you're looking for a boat to hold a large family, this four-bedroom yacht makes for a spacious, elegant getaway offshore.

The interior is bright and airy, with a white-paneled ceiling, sprawling lounge spaces, and a massive kitchen with up-to-date finishes. 

The staterooms and living areas are mostly white with splashes of turquoise, gold, and orange, and objets d'art provide colorful pops. Bathrooms are also large and have plenty of countertop and storage space.

Outside, there's more room to spread out along the perimeter benches, at patio tables, or from the seating area at the back of the ship. 

While the boat stays moored, you can also book private charters with the host or use the complimentary kayaks, stand-up paddleboards, and fishing poles.

Restored vintage yacht in Charleston, South Carolina

Book this Charleston boat on Airbnb

This Charleston stay takes place on a Hatteras motor yacht restored with a big helping of Southern charm. The marina location is peaceful and also ideal for exploring downtown Charleston.

The boat features all-teak interiors and white sofas, as well as simple but inviting bedrooms that can easily sleep a family. The main bedroom has a Full bed and an ensuite bathroom, and the second bedroom has two single beds that are just right for kids.

What should I consider when staying on a boat?

While boats have a lot of charm, not all offer a lot of space, and sometimes bedrooms (whether staterooms or berths) can even be claustrophobic with very limited square footage. Be sure to ask the host questions about the size of the rooms if you have concerns.

Not all boats have super-small living quarters, though. Houseboats, for example, will tend to offer more room to move around than sailboats since they're meant for day-to-day living. Yachts for larger groups can also offer more space. 

Be aware that not all boats have full kitchens or showers so be sure to read up on the amenities and what's onboard versus nearby.

How do I find an Airbnb that's a boat? 

Type in your initial search criteria on the site's landing page, including the number of guests, destination, and dates (or as much of that as you know).

Then, click "more filters," and scroll down to "unique stays." You'll find a box to check that says "boats," and that will bring up the only boats to your results pages.

What is the Airbnb Enhanced Clean program?

The Airbnb Enhanced Clean is a program for hosts that involves learning and getting certified in strict cleaning protocols. These cover everything from wearing personal protective equipment and what cleaning supplies to use to how to clean between guests. All hosts are now required to follow a stringent cleaning plan outlined by Airbnb as part of the program. 

Is it safe to stay in an Airbnb?

The CDC has declared US travel safe for fully vaccinated individuals.

Vacation rentals are also considered safer than hotels by experts, especially completely contained stays like the boats we've outlined. However, it's wise to continue to monitor guidance from the CDC and WHO, and to check state and local guidelines.

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Axel Springer, Insider Inc.'s parent company, is an investor in Airbnb.

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