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Outdoor pool at an Airbnb in Key West
Photograph: Airbnb and Daryl Reiber PhotographyCasa Margarita

The most stunning Airbnbs in Key West

The best Airbnbs in Key West range from adorable bungalows to floating yachts

Megan duBois
Written by
Megan duBois

Imagine Key West: Palm trees swaying in the breeze, a Jimmy Buffett song playing in a dive bar on Duval Street, and the glittering waters of the Gulf of Mexico. Now imagine yourself in one of these stunning Airbnbs in Key West. Yup, bliss. 

Now that we've convinced you to make the trip, all you have to do is choose the best Airbnb in Key West for your preferred type of vacation. Most of the rentable homes on this list are just steps away from the top things to do in the city, including exploring the bustling bar scene downtown, relaxing on the most pristine beaches, and dining in the best restaurants in paradise. So start packing your bags because we've done half the work for you – these are the best Airbnbs in Key West. 

RECOMMENDED: The best hotels in Key West 

Best Airbnb in Key West

Those looking to rent an entire home for their Key West vacation should look no further than Pilar’s Secret. The home is big enough for up to eight guests and is located just off Duval Street – a central spot for groups who want to be within walking distance to most of what Key West has to offer in terms of late night entertainment. When you’re done walking around the city, jump into the pool to cool off before getting ready for a night out on the town.

In the heart of Old Town Key West you’ll find Casa Margarita, a pet-friendly home rental that sleeps up to eight people in three bedrooms. Outside in the courtyard there’s a hot tub and pool for cool nights and warm sunny days. The home is also within walking distance of the most desirable restaurants, shops, museums and entertainment offerings in Key West.

Duval Street duplex
Photograph: Airbnb

3. Duval Street duplex

If staying in the middle of the action on Duval Street sounds like a good time, this two-story duplex with a balcony is the Airbnb for you. The adorable rental sleeps up to eight guests in two bedrooms, with four bathrooms and a decent-sized living room to hang out together. When night falls, step out onto your balcony to people watch as your sip rum runners and White Claws. 

If the idea of a houseboat has ever appealed to you, then consider this Airbnb – a 50-foot-long boat that’s anchored 1.7 miles away from land in the middle of the ocean. The boat sleeps up to six guests, has a small galley-style kitchen and a living area for enjoying dinner and playing board games at night. When you’re ready to head ashore there’s a shuttle that can pick you up in the morning and in the evening to take you to and from Key West.


This stunning Key West condo can accommodate up to two guests in a one-bedroom, one-bathroom space. The building is located right on a private beach, and from this first-floor space, access to the sand is particularly easy. There's also a heated pool and hot tub on premises. Plus, Duval Street is just a five-minute walk away. 

The Wyland Penthouse is conveniently located in downtown Key West and can sleep up to four guests. Located just above the Wyland Gallery on Duval Street, the Airbnb has a living room that leads out to a balcony with French doors and a view of Duval Street. The kitchen was recently redone with all new stainless steel appliances and granite countertops, so you’ll likely want to cook a few meals here instead of always trekking to the nearest restaurant. 


The Island Color Suite is a spacious two-story appartment located right on Duval Street. The rental can accommodate up to six guests in two bedrooms. The small kitchen has plenty of room to whip up breakfast before heading out for the day, and the cozy balcony is a great spot to drink your morning coffee. At night, step out there again for great people watching as your sip on a nightcap or pregame before heading out to the bars yourself.


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