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Key West Airbnbs, Florida Airbnb, Time Out Key West
Courtesy: Airbnb

The best Airbnbs in Key West

From adorable bungalows to floating tiki huts, these are the finest Airbnbs in Florida’s southernmost city

Written by
Megan duBois
Ed Cunningham
Alex Floyd-Douglass
Camila Karalyte

Key West is one of those places that is so idyllic it can be hard to believe it’s actually real. Picture the scene: palm trees swaying gently in the breeze, surrounded by crystalline turquoise waters, basking in year-round sunshine - absolute bliss. If that ain’t the good life, we don’t know what is.

And there are few better ways to properly indulge in Key West than by renting an Airbnb. The city’s finest Airbnbs range from abodes that are mere steps away from the area’s biggest attractions to those that are perfect for lounging by the beach. We’ve sifted through all of Key West’s Airbnb rental options to find the ones that are totally unmissable: read on to find out more.

🏝Why not stay at one of the best hotels in Key West?

Who makes the cut? While we might not stay in every Airbnb featured, we've based our list on top reviews, hosts and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines.

Best Key West Airbnbs

The grand tiki on the Atlantic Ocean
Photograph: Airbnb

1. The grand tiki on the Atlantic Ocean

If we ever wanted to get away from it all and sail off into the sunset in style – we’d do it in a Grand Tiki. Perfect for sitting in bed and watching the sunset before being swayed to sleep by Key West’s gentle waters, this place also comes with a bunch of modern facilities like voice-activated lighting, a TV, and a fridge.

Rooms? One bedroom. Sleeps two guests. 
The mood? Floating paradise. 
Location perks? Enjoy beautiful sunsets along the shoreline, while chilling in the hammock, book in hand. 
Budget range? A luxury escape for two.

The cozy houseboat on Stock Island
Courtesy: Airbnb

2. The cozy houseboat on Stock Island

Want to stay – quite literally – on the water? This oceanfront houseboat is exactly that. As it bobs along the clear waters of Key West, you'll find yourself feeling at home instantly. From the dining deck to the well-equipped bedrooms, this Airbnb makes for one of the most unique stays you'll find in the whole of Florida. And that's saying something. Cook up a storm on board or take a leisurely stroll along the harbor to explore one of the many restaurants and bars it has to offer. And if you're looking for a nightlife vibe, catch an uber to Duval Street – it won't disappoint. 

Rooms? One bedroom. Sleeps six guests. 
The mood? Oceanfront oasis.
Location perks? The covered patio is a great spot for views of the bay. 
Budget range? Not cheap, but certainly knows how to hit the spot if you're looking for a peaceful retreat.

The oceanview studio in Upper Duval
Photograph: Airbnb

3. The oceanview studio in Upper Duval

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. 

Rooms? One-bed apartment. 
The mood? Vintage resort vibes. 
Location perks? A heated pool, hot tub, free parking and easy access to the beach – all that's left now, is a cocktail with one of those umbrellas on top.  
Budget range? An affordable couple's getaway. 

The pet-friendly casa in Old Town
Photograph: Airbnb and Daryl Reiber Photography

4. The pet-friendly casa in Old 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.

Rooms? Three bedrooms. Sleeps eight guests. 
The mood? Retro and beachy.
Location perks? The tropical landscaping that surrounds the courtyard will make you feel like you're on a private island. 
Budget range? Decently priced for large groups. 

The modern duplex on Duval Street
Photograph: Airbnb

5. The modern duplex on Duval Street

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. 

Rooms? Two bedrooms. Sleeps eight guests.
The mood? Livin' it up by the pool. 
Location perks? Enjoy the charming West Indian-inspired grounds, complimentary breakfast, and bike rental service.  
Budget range? Right on the noggin for an affordable group trip.

The Wyland penthouse in downtown Key West
Photograph: Airbnb

6. The Wyland penthouse in downtown Key West

The Wyland Penthouse is conveniently located in downtown Key West and can sleep up to six 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. 

Rooms? Two bedrooms. Sleeps six guests.
The mood? Elegant, but still beachy and relaxed. 
Location perks? Just 10 minutes away, you'll find Truman Waterfront Park where kids can have a whirl with the sprinklers. 
Budget range? A luxury price tag.

The island suite on Duval Street
Photograph: Airbnb

7. The island suite on Duval Street

The Island Color Suite is a spacious two-story apartment 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.

Rooms? Two bedrooms. Sleeps six guests. 
The mood? Cool-toned and cozy. 
Location perks? Spotlessly clean and centrally located – great for enjoying a short walk to the beach. 
Budget range? A bit pricier but worth it for such high style and a cracking (figuratively, that is) balcony.

The luxury vacation home near Bahama Village
Photograph: Airbnb and Daryl Reiber Photography

8. The luxury vacation home near Bahama Village

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 of 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.

Rooms? Three bedrooms. Sleeps eight guests. 
The mood? Beachy, ambient and cosy.
Location perks? From the BBQ grill to the whimsical string lights, every detail is taken care of.
Budget? A lavish vacation indeed.

The stunning hideaway near Duval Street
Photograph: Airbnb and Daryl Reiber Photography

9. The stunning hideaway near Duval Street

Half a block away from Duval Street, but located on a quieter street, is Mango Hideaway. The rental can accommodate up to three guests in a one-bedroom, one-bathroom bungalow. Just off the private deck is a hot tub – a beacon after a long day of walking around Key West. 

Rooms? One bedroom. Sleeps three guests. 
The mood? Tropic bliss. 
Location perks? If you fancy going for a swim, there's a shared pool just a block away.  
Budget range? Spenny.


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