Last Updated January 11, 2021 1/11/2021

12 Coolest Airbnbs in the Florida Keys

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Known for its tropical atmosphere, seafood restaurants and memorable outdoor adventures, the Florida Keys are perfect for when you want an island escape. But the palm tree-filled scenery comes at a hefty price tag, as most hotels often run higher than $200 a night. Fortunately for budget-conscious travelers, there’s an alternative option: Airbnb. To help you make the most of your vacation in the Sunshine State, we’ve highlighted the coolest Airbnbs in the Florida Keys, from a floating barrel cabin to a waterfront bungalow.


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Tavernier - Key Largo Tavernier

Tavernier - Key Largo

Get away from it all in this luxury suite, which sits on a one-acre private gated estate. Sitting directly on the Gulf of Mexico, your doors open up to water views and secluded beach area. Outdoor adventures are encouraged here, including snorkeling and day trips to the Everglades, while it’s easy to take it easy with the outdoor grill and hammock. When hunger strikes, you’re within walking distance to local eateries.

Four Bedroom Villa - Duck Key Four Bedroom Villa
Four Bedroom Villa

Four Bedroom Villa - Duck Key

Make a splash with your family or group of friends at this four-bedroom villa in Duck Key, which features a sparkling outdoor pool that’s perfect for cooling off in Florida’s heat. Up to 10 guests can split the bill at this luxurious getaway, where a spacious kitchen, living and dining room and outdoor area offer enough space to make this place your home. There’s even a private lanai off the master bedroom and a back patio with a grill.

Real World MTV House - Key West Real World MTV House
Real World MTV House

Real World MTV House - Key West

If you’re a Real World fan you’ll love staying at this house in Key West, which was used to film the 2006 season. Large groups and families can take advantage of the 500 feet of oceanfront property at the “mini resort”, which has 10 bedrooms and 14 plasma TVs, while there’s also access to kayaks, paddleboards bikes and a gym. If that’s not enough to keep you busy, there’s also a pool table, racket ball court and boat dock.

Mermaid Cove - Key West Mermaid Cove
Mermaid Cove

Mermaid Cove - Key West

Comprised of four cottages, Mermaid Cove can sleep up to 12 guests, each cottage featuring its own private entrance to the courtyard and outdoor patio. Set on Duval Street, it features a prime location for exploring the city within walking distance to major sights. Enjoy the tropical decor and outdoor patio with a BBQ grill, as well as the flat-screen TVs, kitchen/kitchenettes, air conditioning and French doors. Don’t forget to say hello to the resident iguana “Dino”.

Waterfront Bungalow - Marathon Waterfront Bungalow
Waterfront Bungalow

Waterfront Bungalow - Marathon

Soak up the Bohemian vibes of this two-bedroom waterfront bungalow in Marathon, where you’ll most likely spend the bulk of your time relaxing in the outside screened-in porch. There’s a private dock for parking your own boat, and the bungalow is equipped with everything you need, including fishing poles, chairs and games for the family to keep entertained. You’re also within walking distance from grocery stores and restaurants.

Bella Vita - Key West Bella Vita
Bella Vita

Bella Vita - Key West

Couples who love color will fall for this charming one-bedroom condo in Old Town, less than a block from Duval Street. It features a wrap-around porch with chairs, a spacious living room with a leather sofa and galley kitchen with bar seating as well as two flat-screen Smart TVs and Bluetooth stereo system. When you’re ready to explore, the Southernmost Point and Hemingway House are just a few blocks away.

Private King Room - Key West Private King Room
Private King Room

Private King Room - Key West

Located a few blocks from Duval Street, this private room features a king-size bed, flat-screen TV, complimentary Wi-Fi and a private bathroom. Embrace the Florida Keys tropical vibe at the two outdoor pools and Jacuzzi, then sip cocktails from the on-site bar or grab a pick-me-up Starbucks coffee. Continental breakfast comes with the room as a part of The Southernmost Inn, and adults-only property.

Caribbean Cottage - Marathon Caribbean Cottage
Caribbean Cottage

Caribbean Cottage - Marathon

You can’t get cuter than this Caribbean-style cottage in Marathon with its pastel-colored exterior. The one-bedroom cottage is perfect for couples, families or traveling friends, nestled within an enclave of 10 cottages, featuring a picnic area, tiki bar and hammocks. You’re only a half block from the Gulf of Mexico and includes two queen-size beds, a seating area and full kitchen.

Tiny House on the Water - Key Largo Tiny House on the Water
Tiny House on the Water

Tiny House on the Water - Key Largo

Only about an hour from Miami’s top attractions, you can embrace tiny home living in this tiny house in Key Largo, where you’ll be located within a private community with two beach areas, a boat ramp and a heated swimming pool. Enjoy beach volleyball, let the kids loose at the children’s play area and entertain at the gazebo with two large dining tables. Active travelers will appreciate the two kayaks and standup paddleboards for guests.

Island City House Hotel - Key West Island City House Hotel
Island City House Hotel

Island City House Hotel - Key West

Technically this is no longer listed on Airbnb, but the oldest operating guesthouse in Key West, the Island City House Hotel boasts a rich history, a part of the Key West Historic Market Tour. The three-story Victorian mansion was originally built as a private home for a wealthy Charleston merchant family in 1880, then converted into a hotel in 1912 in anticipation of the railroad’s arrival. The suite is furnished with Victorian antiques, lace curtains and hardwood floors, while a sparkling pool, infrared sauna and large sunning deck are adding perks.

Walking Distance to Beach - Key West Walking Distance to Beach
Walking Distance to Beach

Walking Distance to Beach - Key West

Discover a prime location at this Key West gem, just a short walk from Mallory Square, Duval Street and Zachary Taylor Park, popular for swimming, snorkeling and relaxing on hammocks. The one-bedroom unit is located in a gated community, which has a heated pool, while the covered deck is perfect for enjoying a glass of wine or a cup of coffee. If you want to cruise on two wheels, there’s rental bikes available.

Winter Tavernier - Key Largo Winter Tavernier
Winter Tavernier

Winter Tavernier - Key Largo

Up to four guests can fit in this vacation rental, which is designed as an open floor loft with French doors. You’ll have access to kayaks, paddleboards, snorkeling equipment and bicycle rentals at this beautiful estate, where you’ll be surrounded by gorgeous the natural beauty of the foliage and fauna. There’s even a living aquarium in the lagoon area, as it’s part of the Marine Sanctuary that helps save local sea life.

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