floriday keys airbnbs

The 10 Dreamiest Airbnbs in the Florida Keys

We've found them so you can spend more time in the sun than searching for the right spot.
By Kendall Cornish
April 18, 2021
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.

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

florida keys airbnb
Credit: Courtesy of Airbnb

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

key west houseboat
Credit: Courtesy of Airbnb

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

airbnb vacation rental yellow house treetop old town florida keys
Credit: Courtesy of Airbnb

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

florida keys airbnb vacation home rental
Credit: Courtesy of Airbnb

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

florida keys airbnb
Credit: Courtesy of Airbnb

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

florida keys airbnb vacation home rental
Credit: Courtesy of Airbnb

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

mango hideaway airbnb florida keys
Credit: Courtesy of Airbnb

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

searenity florida keys airbnb vacation home rental
Credit: Courtesy of Airbnb

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

florida keys airbnb vacation home rental
Credit: Courtesy if Airbnb

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

gallery rooftop airbnb vacation rental florida keys
Credit: Courtesy of Airbnb

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.

Love a great deal? Sign up for our T+L Recommends newsletter and we'll send you our favorite travel products each week.