The 13 best Airbnbs in Key West

An ideal Key West vacation strikes the perfect balance between subtropical serenity and a raucous good time—and where you stay makes all the difference. At Secret Villa II (the host also owns Secret Villa I, which can be booked together as a compound), you’re positioned on a quiet private lane just a block off Duval Street, the heart of Key West’s party district. And one block is really all you need to settle into Key West’s more languorous side, all the while knowing that the party awaits at your doorstep. A newly renovated two-story, three-bedroom home with a private courtyard swimming pool, this villa is incredibly spacious by Key West standards with plush furnishings, a modern kitchen and dining tables both indoors and out on the covered patio by the pool. With two master bedrooms upstairs, each with its own en suite bathroom, they share a spacious balcony, ideal for lounging with coffee in the morning with the roosters or a nightcap before bed beneath the star-studded sky.

Rooms? 3 bedrooms, 3 baths, sleeps 6.

The mood? Luxury residential living in true Key West style.

Location perks? Just a block off Duval Street on a private lane in the heart of Old Town.

Budget range? Top end.

Why would a local recommend it? This lux “secret villa” comes with all the creature comforts of residential living in an unbeatable location.

Round up a party of five of your best friends and make your way to this idyllic “conch” cottage on Southard Street in a quiet, residential section of Old Town and get ready spend a vacation in Key West living like the locals do. This two-story, three-bedroom cottage has all the trappings of classic Key West architecture: a covered front patio surrounded by lush foliage, cathedral ceilings, a private courtyard swimming pool and an outdoor shower. And while it oozes historic charm, you’ll also enjoy the modern luxuries of an updated kitchen with granite countertops, stainless steel appliances and a gas range. Bathrooms are also modern and fresh, featuring stone vessel sinks, glass-enclosed showers and tile and granite finishes. The epitome of indoor-outdoor living, there’s a dining room and a shaded table on the patio by the pool for entertaining. For added comfort, there’s also a washer-dryer and a private driveway with a parking space, a rarity in Old Town.

Rooms? 3 bedrooms, 2.5 baths, sleeps 6.

The mood? Wasting away again in Margaritaville… in style with a pool.

Location perks? A picturesque residential corner of Old Town, you’re still a quick bike ride to all the action on Duval Street.

Budget range? Reasonable when splitting amongst a group.

Why would a local recommend it? This conch cottage on Southard Street offers visitors the feeling of living like a local. With a courtyard swimming pool and cathedral ceilings, it’s classic Key West all the way.

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.

Want to stay – quite literally – on the water? This oceanfront houseboat will see you doing 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.

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. 

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. 

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 you 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 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 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 you 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.

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.

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.

With a tasteful nautical design, impressive communal pool and easy access to the beach, you can't go wrong with this Key West apartment. Everything is sleek and up-to-date, ideal for young families who wouldn't mind getting a few new Instagram pics out of the trip. The brand new mattresses will ensure a restful night's sleep for all, and we can bet that by the end of your stay you'll be more than tempted to return the following year. 

Rooms? Two bedrooms. Sleeps six guests. 
The mood? Elegantly renovated. 
Location perks? Close to the beach and pretty much in the middle of town.   
Budget range? Above average price for an above average stay. 

Wake up the the sound of waves as you embark on a blissful stay at this traditional property that sits right on Key West's only natural beach. The dark wood interiors bring the warmth and homely vibes, while the balcony provides the perfect setting for watching the sun rise or set. You can use the facilities at the neighboring resort, including the pool and benefit from being a short walk from many of Key West's best attractions and restaurants.  

Rooms? One bedroom. Sleeps two guests.  
The mood? Classic and cozy. 
Location perks?  On the quiet side of Key West, just a short walk to the more buzzing area of Duval Street.  
Budget range? Pricey, but worth it for a special trip.