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 is some of the best in the world. But, 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 book.
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.
To book: airbnb.com, $385/night
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.
To book: airbnb.com, $281/night
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.
To rent: airbnb.com, $275/night
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.
To rent: airbnb.com, $295/night
Island Color Suite
Ideal for travelers who love to be central — both close to the water and to restaurants — this suite will give you a taste of what it’s truly like to live in the Florida Keys.
To rent: airbnb.com, $458/night
Marathon House on the Water
This gorgeous waterfront home is the epitome of luxury beachside living. It’s close to the Sea Turtle Center, has plenty of accommodations for modest groups, and plenty of indoor and outdoor seating for family meals.
To rent: airbnb.com, $197/night
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.
To rent: airbnb.com, $265/night
Searenity Waterfront Vacation Rental
This vacation rental’s got it all if you’re planning on spending most of your time hanging out in the sun, from a dock for remotely pulling up in your boat to a pool and a tiki hut for outdoor festivities.
To rent: airbnb.com, $380/night
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.
To rent: airbnb.com, $841/night
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 do your heart’s desire.
To rent: airbnb.com, $472/night
Kendall Cornish is an e-commerce editor at Travel + Leisure. She’s never lived anywhere longer than three years, but currently resides in Brooklyn with her cat and beloved Dyson vacuum. You can follow her on Instagram at @kendall.cornish.
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