Key West is not only a tropical paradise that you don’t have to board a plane to reach, but it’s teeming with exciting attractions, from historical sites and trendy restaurants to a pleasant nightlife. Craving days of snorkeling, biking downtown, eating key lime pie and shrimp? Consider renting an Airbnb to totally immerse yourself in the Key West way of life. Many require a 28-night stay to comply with the Homeowners Association, but that’s a great excuse to stay and play for a while. From quaint little pools to airy pastel aesthetics, these are our favorite Key West Airbnbs.


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Enchanting Seaside Cottage Enchanting Seaside Cottage
Enchanting Seaside Cottage

Enchanting Seaside Cottage

Looking for a place to spend the summer? Just a mile from Mallory Square sits this precious bungalow with the perfect blend of tropical and homey essence. There couldn’t be a more ideal abode to settle into for a month of exploring the history, scenery and food of Key West. Take advantage of the private pool, off-street parking and prime location near all the beach action, where you can stroll the shoreline or try your hand at paddleboarding. A bonus for families, there’s even a washer and dryer as well as central air conditioning.

Dog-Friendly Home with Private Pool Exterior and pool
Exterior and pool

Dog-Friendly Home with Private Pool

Pups can stay with you at this two-level, full-sized home surrounded by palms and bright colors. Climb downstairs to find patio lounging space and views of the gorgeous property and heated pool below. Blue shutters and a paver lined backyard space couldn’t be more perfect for a day of grilling up Key West pink shrimp and swimming. This home too requires more long term stays, but since it sleeps up to eight people, you can bring the whole family. Bonus—two private parking spots are available to guests.

1 Bedroom Cottage Exterior front porch
Exterior front porch

1 Bedroom Cottage

Baby blue and snug as bug, this wee cottage sits right beside Duval Street. Inside you’ll find a kitchen, bath, living area and one bedroom, which create more than enough space for vacationers. While you won’t find a pool, the location amongst some of the more notable spots in Key Kest by far makes up for it. Opt for a snorkeling day cruise or sample the best Key Lime pie in Key West instead!

Dog-Friendly Home with Private Pool Dog-friendly home with private pool
Dog-friendly home with private pool

Dog-Friendly Home with Private Pool

Outdoor spaces at this dog-friendly, dual-level home are something out of a dream, with elevated porches and other cozy patio space with hammocks to lounge. Let’s not forget the perfectly “Key West” pint-sized pool out back, which is surrounded by tables, umbrellas and swaying palms. Inside is modern and fresh, with a variance of sleeping arrangements, from rooms with twin-sized mattresses to king and queen-sized beds. With all the amenities from home, including a washer and dryer, it would be a piece of cake to meet the 28-night requirement.

Breezy Florida Home Shared pool space
Shared pool space

Breezy Florida Home

Whitewashed wood walls and cheerful hues give this bungalow a ship-like design. The shower is adorned with a beautiful aqua tile, which is consistent with the overall coastal theme. A lovely, canvas shaded pool is shared with the neighbors but remains an overall quiet place to soak in this Florida Key. There’s a 28-night minimum, but it will be easy to make this your new home away from home with its easy access to Old Town dotted with restaurants and shops as well as Higgs Beach, just a few blocks south.

Walk to Beach, Duval, Mallory Living room and porch space
Living room and porch space

Walk to Beach, Duval, Mallory

Walk to one of the few swimmable beaches on the island from this bright condominium, which accommodates up to three guests quite comfortably. In addition to the vibrant interior space, you’ll find a breezy porch with cushy loungers, and an inviting pool available to the complex. Mallory Square is just around the corner, while Zachary Taylor Park is a short walk away, where you can swim, snorkel or hang out in the hammocks at the beach.

Bird of Paradise Large pool area
Large pool area

Bird of Paradise

Looking for something a bit out of the bustle of it all? This Airbnb is perfect for you. Bird of Paradise is nestled in a quiet neighborhood and features its own fenced-in backyard oasis. The pool is significantly larger than most you’ll find among Airbnb locations in Key West, and the floor-to-ceiling French doors connect the indoor living room to the beautiful outdoor area. Six guests can easily bunk up within the tropical-chic haven.

Stylish Home with Private Pool Tiled pool in back
Tiled pool in back

Stylish Home with Private Pool

The inside of this Airbnb says modern luxury, while the outdoor recreation area with black and white tile pool screams old Key West. Since you have to book 28 nights here, major amenities like a spacious kitchen, washer and dryer and free parking are welcomed perks. With three bedrooms and two and a half baths, the full home can house up to six people. Some of the best attractions in Key West, including Hemingway House and the Southernmost Point of the U.S., are a short walk away.

Waterfront Home with Private Pool Waterfront Home with Private Pool
Waterfront Home with Private Pool

Waterfront Home with Private Pool

This seven-bed, waterfront mansion with views is like a movie set. Warning, you may never leave the beautiful wood-planked porch. Bedrooms are elegant and the bathtubs are mammoth-sized as well, with the master featuring jacuzzi jets. The open floor plan includes central air conditioning, Wi-Fi and large flat-screen smart TVs. Outside, there is a private pool with covered lounging space, lots of seating and a grill. The home tops out at 2,725 square feet and the required stay is 28 nights.

Old Town Room Onsite private pool
Onsite private pool

Old Town Room

Offering a quiet and secluded room with a private entrance, you can experience an authentic Key West getaway at this Airbnb. The pool, which guests have private access to is surrounded by a mango tree and rich planked wood decking. A Keurig coffee maker and tea kettle with a selection of coffee and teas await alongside a convenient mini-fridge. Lounge in comfy chairs and enjoy this secluded oasis, then access the heart of Old Town on the other side of the foliage or head to the beach with your complimentary beach towels. Duval Street is just minutes away by foot, as are the best eateries in Key West.

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