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- Hotels + Resorts
- Vacation Rentals
We’ve found them so you can spend more time in the sun than searching for the right spot.
When it comes to East Coasters seeking sun during the cooler months (or year-round), the Florida Keys are literally a go-to. This trail of tropical islands has some of the softest sand and sunniest days east of Texas. If you’re an ocean or water sport enthusiast, the snorkeling, fishing, and scuba diving are some of the best in the world. Moreover, with attention paid to the times, it can also be one of the dreamiest locations for an extended stay if you’re able to work remotely.
Each of the following Airbnbs are hosted by “Superhosts” and feature all of the trappings you’d expect and desire from a tropical vacation, from sun-soaked living spaces to easy beach access. Bringing your pup? We’ve got some options for you. Bringing the whole family? There are some Airbnbs on this list that allow everyone to both have their space and come together.
Without further ado, these are the dreamiest Airbnbs in the Florida Keys. It’s a miracle some are still available to rent, so don’t wait to explore.
Turtle Beach Cottage Private Oceanfront Paradise
This beachfront home has it all — a hot tub, beach access, a beach view from the bedroom, a variety of outdoor seating, and palm trees galore. It’s a true stateside tropical paradise.
Key West Houseboat
The ultimate remote vacation isn’t even on land — it’s on an old-school style houseboat in the Florida Keys. This one comes with its own floating platform, so you can cruise in the sun or enjoy a glass of bubbly while watching the sunset.
Treetop Studio Old Town Key West
This little yellow house has a treetop studio with a hot tub calling all our names for a quick vacay or long-term remote work.
Beach Bungalow With 60′ Dock
This waterfront bungalow has modern appliances and a well-kept garden for a comfortable, seamless, and idyllic vacation in the sunshine state.
Island Color Suite
This suite is ideal for travelers who love to be central — both close to the water and to restaurants — allowing you to experience what it’s truly like to live in the Florida Keys.
Marathon House on the Water
This gorgeous waterfront home is the epitome of luxury beachside living. It’s close to the Sea Turtle Center and offers plenty of accommodations for modest groups, along with ample indoor and outdoor seating for family meals.
Mango Hideaway
This little yellow home has all you need for an intimate getaway — just a bed, outdoor seating, a hot tub, a grill, and more just steps away from Duval street.
Searenity Waterfront Vacation Rental
This vacation rental has it all if you’re planning on spending most of your time hanging out in the sun. It includes a dock for pulling up your boat, a pool, and a tiki hut for outdoor festivities.
Two-bedroom Sunset Bungalow
This two-bedroom Airbnb is sun-soaked and honors its name by being an ideal spot for watching the sun set in the evenings, glass of rosé in hand.
Wyland Penthouse
This penthouse atop a gallery in town is an urbanite’s ultimate escape, complete with plenty of privacy and space, but with the option to people-watch and enjoy the vibrant atmosphere.
