The 10 best Airbnbs in Key West

Neighborhood: Old Town

A block or so from Duval Street, Secret Villa II gives you the best of both Key West worlds: all the bars, restaurants and live music you could want, plus a private tropical hideaway to retreat to when you’ve had enough of them. The three-bedroom, three-bathroom home has plenty of room for six, with two king bedrooms upstairs and a queen room downstairs, plus a big living room and fully equipped kitchen. Outside is where things really come together, though, with a heated private pool tucked behind a fence and surrounded by lush greenery, a grill for poolside BBQs and a terrace for evening drinks. In other words, go out and make questionable decisions on Duval, then come home and float them off.

Time Out tip: The quiet private lane means you can be close to the action without sleeping in it. Duval Street is about a block away, while restaurants, bars, galleries, museums and nightlife across Old Town are all within walking distance.

Sleeps: 6 guests.

Perks: Private heated pool, tropical garden, poolside grill, three bathrooms, fully equipped kitchen, dedicated workspace, fast Wi-Fi and parking for one mid-sized car or small SUV.

Price: From $9,670 for five nights. 

Neighborhood: Key West Harbor

Forget checking into a Key West hotel: The Grand Tiki puts you in your own private floating bungalow, anchored out in the harbor with water in every direction. The one-bedroom retreat has a king bed, panoramic French doors and a deck where you can hammock, paddleboard, snorkel or simply watch the sun disappear into the horizon. There are plenty of modern comforts on board, including air conditioning, a hot shower, mini fridge and microwave, but the best bit is being properly out on the water, with underwater lights that bring fish into view after dark. It’s private, peaceful and about as far from an ordinary Key West stay as you can get.

Time Out tip: The Grand Tiki is accessible by boat only, with arrival and departure coordinated via a local water shuttle. Bring your food and drinks with you, then settle in as once you’re aboard, the whole floating bungalow is yours.

Sleeps: 2 guests.

Perks: Private floating bungalow, king bed, ocean views, private deck, hammock, paddleboards, snorkeling gear, swim ladder, underwater lighting, air conditioning, hot shower, Wi-Fi, mini fridge and microwave.

Price: From $900 for a night.

Neighborhood: Old Town

Set on a quiet residential street in Old Town, Southard Comfort is the sort of Key West vacation rental that makes you feel like you’ve temporarily joined the neighbourhood. The three-bedroom, 2.5-bathroom home has vaulted ceilings, a welcoming front porch and plenty of indoor-outdoor space, with French doors opening from the living room onto a private courtyard and cocktail pool. There’s also a gas grill and outdoor dining area for lazy lunches, while inside you’ll find a well-equipped kitchen and enough room for six to spread out. Add in a private driveway (a particularly handy perk in Old Town) and you’ve got a very good excuse to settle into island life for a few days.

Time Out tip: You’re four blocks from the Historic Seaport and six blocks from Duval Street, so the bars, restaurants and general Key West commotion are close by without being right outside your front door.

Sleeps: 6 guests.

Perks: Private cocktail pool, outdoor shower, gas grill, outdoor dining area, 2.5 bathrooms, fully equipped kitchen, washer-dryer, air conditioning, Wi-Fi and private parking for one vehicle.

Price: From $3,050 for four nights. 

Neighborhood: Downtown Key West

Above the Wyland Gallery, this two-bedroom penthouse puts you slap bang in the middle of downtown Key West, with shops, restaurants and entertainment right outside the door. Inside, there’s plenty of room for six, with two king bedrooms, a huge living room with 15-foot ceilings and a fully equipped kitchen. But the real star is the private rooftop terrace, where you can sit above the buzz of Duval Street and watch the action below. There’s even a little off-street parking, which is handy when you’re staying this centrally.

Time Out tip: Despite being directly on Duval Street, guests say the penthouse is surprisingly quiet. And when you fancy escaping the crowds, Truman Waterfront Park is about a 10-minute walk away.

Sleeps: 6 guests.

Perks: Private rooftop terrace, two king bedrooms, sofa bed, fully equipped kitchen, 1.5 bathrooms, washer-dryer, air conditioning, Wi-Fi, TV and one free off-street parking space.

Price: From $990 for a night.

Neighborhood: Downtown Key West

Right in the middle of Duval Street, Island Color Suite puts you within easy reach of Key West’s restaurants, shops, bars and entertainment. The two-storey apartment sleeps six across two bedrooms, with an open-plan living room and a fully equipped kitchen with new stainless steel appliances and quartz countertops. But the best bit might be the private balcony, where you can sit with a morning coffee, watch people go by or pour yourself something tropical before heading out for the night. It’s a prime spot for anyone who likes their Key West vacation rental with a little street life.

Time Out tip: The location is hard to beat, but the trade-off is noise: being right on Duval means you’ll hear the buzz of the street, particularly at night and in the early morning. If you’re here to make the most of Key West’s nightlife, though, that’s hardly a dealbreaker.

Sleeps: 6 guests.

Perks: Private balcony, two bedrooms, fully equipped kitchen, 1.5 bathrooms, washer-dryer, air conditioning, Wi-Fi, smart TVs and free parking.

Price: From $600 for a night.

Neighborhood: New Town / Atlantic Boulevard

Anchor Drop gives you a little more breathing room than the average Key West stay, with a beautifully renovated two-bedroom condo at the 1800 Atlantic Condominiums. Inside, there’s an open-plan living space, two full bathrooms, a king bedroom and a second room with twin beds that can convert to a king, plus a queen sofa bed for extra sleeping space. The private balcony is a lovely spot for morning coffee, while downstairs you’ve got an oceanfront heated pool, huge hot tub, tennis courts, a sauna and fitness centre. Smathers Beach is around a 20-minute walk away, too, so you can easily swap pool time for sand-and-sea time.

Time Out tip: You’re not right in the middle of Old Town, so a car, bike or taxi will come in handy for nights out on Duval Street. The upside is that you get a quieter, more resort-like base, and one assigned garage parking space.

Sleeps: 6 guests.

Perks: Oceanfront shared pool and hot tub, private balcony, tennis courts, sauna, fitness centre, two bathrooms, fully equipped kitchen, Wi-Fi, air conditioning and one assigned garage parking space.

Price: From $1,675 for three nights. 

Neighborhood: Garrison Bight

With a private boat slip, marina views and a heated pool just downstairs, this spacious Garrison Bight condo is a pretty good setup for a Key West escape on the water. The two-bedroom apartment has more than 1,200 square feet to spread out in, with a king bedroom, a second room with two queen beds, two bathrooms and an open-plan living space leading onto a private balcony overlooking the marina. Bring your boat and head out from the dock, or spend the day by the pool before firing up the BBQ. When you fancy exploring, Bayview Park is right next door and Duval Street and the Historic Seaport are about a mile away.

Time Out tip: The boat slip is usually included, but it’s temporarily limited during the marina improvement project, so check availability with the host before bringing your boat. If you’re staying without one, there’s still plenty to do nearby, and the waterfront setting and easy access to downtown make a nice change from being right in the thick of Duval Street.

Sleeps: 8 guests.

Perks: Private boat slip when available, heated pool, waterfront balcony, marina views, two bathrooms, fully equipped kitchen, washer-dryer, Wi-Fi, free parking, elevator, BBQ grills and pet-friendly accommodation.

Price: From $380 for a night.

Neighborhood: Key West Harbor

Forget the hotel room: Happys Houseboat gives you your own little floating escape, anchored offshore with nothing but water and wide-open views around you. The one-bedroom boat has a queen bed, full kitchen, bathroom, air conditioning and a top deck made for sunset-watching and stargazing, while the supplied skiff means you can nip back to shore whenever you fancy. There are also two kayaks for getting out on the water, and the whole setup is wonderfully private. This is a proper houseboat experience for anyone who’d rather wake up on the bay than beside a hotel pool.

Time Out tip: You’ll need to be comfortable driving the skiff and with the basics of being on a boat. The dock is centrally located, with restaurants and grocery stores nearby, and downtown is around a five-minute bike ride away.

Sleeps: 3 guests.

Perks: Private houseboat, queen bed, skiff, two kayaks, top deck, harbour views, kitchen, full bathroom, air conditioning, Wi-Fi, free parking and private outdoor space.

Price: From $580 for a night.

Neighborhood: Old Town

Half a block from Duval Street, Poolside Paradise is the kind of Key West vacation rental where you can spend the morning sightseeing and the afternoon doing absolutely nothing. The three-bedroom, 2.5-bathroom home sleeps six, with a king bedroom, queen bedroom and upstairs twin room, plus a fully equipped kitchen, vaulted living room and plenty of space to spread out. Outside, the private heated and cooled pool and spa sit between the two cottages, with a covered dining area for six and an outdoor shower. And because almost everything you’ll want to see is walkable, there’s no need to spend your holiday worrying about the car.

Time Out tip: Make the most of that private pool and spa in the afternoon, when you’ve had your fill of sightseeing. The retractable awning over the dining area also means you can linger outside over lunch or drinks without roasting in the Key West sun.

Sleeps: 6 guests.

Perks: Private heated/cooled pool and spa, outdoor shower, covered outdoor dining area, fully equipped kitchen, 2.5 bathrooms, washer-dryer, Wi-Fi, smart TVs, air conditioning, EV charger, pet-friendly and private parking.

Price: From $6,750 for five nights. 

Neighborhood: Key West canalfront

Bring the boat, the dog and your appetite for pool days: this peaceful three-bedroom home sits right on a Key West canal, with 66 feet of waterfront and a private heated pool tucked into a lush backyard. Inside, there’s a king bedroom and two queens, a fully equipped kitchen, plenty of space to spread out and a dedicated workspace, while outside you’ve got a grill, fire pit and outdoor shower for making the most of the tropical weather. There’s even a community boat ramp just 100 feet away, and with Old Town and the beaches within easy biking distance, you can swap canal-side calm for Key West action whenever you fancy.

Time Out tip: If you’re bringing your own boat, you can tie up directly at the property, making this a particularly good base for getting out onto the water. And once you’re back, the pool and fire pit are ready for the post-adventure wind-down.

Sleeps: 6 guests.

Perks: Private heated pool, canal frontage, boat tie-up, fire pit, grill, outdoor shower, three bedrooms, 1.5 bathrooms, fully equipped kitchen, washer-dryer, Wi-Fi, dedicated workspace, pet-friendly and free parking.

Price: From $3,320 for seven nights.