Florida Keys Vacation Rentals

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Make Florida Keys your next getaway—choose from 346 great vacation rentals

Delightfully warm weather, a tropical atmosphere, and plenty of beach access are just a few of the benefits of our Florida Keys vacation rentals. From fishing to fresh local cuisine to colorful history, the flavors of the Keys are sure to delight any visitor. This legendary string of islands draws travelers back year after year, and our beach house rentals set the scene for the Florida Keys magic they all know and love.

Explore Florida Keys house rentals, condo rentals, duplexes, and more


House rentals

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Condo rentals

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View 27 Duplexes

Florida Keys vacation rentals for every getaway

Dog-friendly Hot tub Internet
Tropical Sabbatical
1 Bedroom | 2 Bath | Sleeps 6

Tropical Sabbatical - Cudjoe Key, FL

$240 avg / night
Sunrise Suites - Paradise Escape 407
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Paradise Escape 407 - Key West, FL

$355 avg / night
Pelico Palms - Sunset Cottage
2 Bedroom | 2 Bath | Sleeps 5

Pelico Palms - Sunset Cottage - Sugarloaf Key, FL

$434 avg / night
Pelico Palms - Villa
4 Bedroom | 4 Bath | Sleeps 12 (7 Adults Max)

Pelico Palms - Villa - Sugarloaf Key, FL

$1,149 avg / night
Sunrise Suites - Big Kahuna Suite 202
2 Bedroom | 2 Bath | Sleeps 4

Sunrise Suites - Big Kahuna Suite 202 - Key West, FL

$328 avg / night

View 341 more homes

Recent Florida Keys vacation rental reviews

Clean, spacious, updated and beautiful property/location. I will be returning!
Jd F. | Aug 2022
We were blown away with the nautical finished inside this unit. The Florida Keys vibes surrounded us in every room, from the upscale kitchen to the mermaid bathroom! This is the perfect getaway located right in the middle of the Keys. The options are endless, we loved the fact there were great dining options within walking distance and our day trips from Islamorada to Key West were easy drives in both directions.
Capt. Ryan H. | Aug 2022
Conveniently located, comfy beds, plenty of room, and clean!
Brenda A. | Aug 2022
Florida Keys Frequently Asked Questions

Yes, 145 of our Florida Keys homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 345 of our Florida Keys vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Florida Keys vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Florida Keys team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Florida Keys, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where are the Florida Keys?

The Florida Keys are a chain of coral reef islands off the southern tip of Florida. Beginning 15 miles from Miami and extending in an arc toward Key West, the islands divide the Gulf of Mexico and the Atlantic Ocean. The islands are connected by a long stretch of road, the famous Overseas Highway.

The inviting climate can be described as a “tropical savannah,” making this area a beloved vacation destination for many. Our Florida Keys beachfront rentals, beach houses rentals, and cottages give vacationers the chance to experience the best of the area firsthand.

Things to do around our Florida Keys vacation rentals

With a storied history and lively nightlife, Key West is immensely popular for good reason. Retirees, young travelers, and water sports enthusiasts will all find something here to their taste. Brunch, sunny strolls, and afternoons out on the water are the foundations of a Key West getaway, and a vacation home with a private pool doesn't hurt, either.