Florida Keys Vacation Home Rentals

Compare 378 vacation rentals.
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Make Florida Keys your next getaway

Escape to the Florida Keys and indulge in the delightfully warm weather, tropical atmosphere, and pristine beaches near our vacation rentals. Our beachfront and resort-style rentals in the Florida Keys set the scene for an unforgettable experience you'll cherish forever. Experience the magic of this legendary chain of islands that draws travelers back year after year by staying with Vacasa.

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

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House rentals

View 178 House rentals
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Condo rentals

View 102 Condo rentals
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Duplexes

View 37 Duplexes

Popular amenities for Florida Keys vacation rentals

Popular
Dog-friendly Hot tub Internet
Wahoo Way On Duval
1 Bedroom | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$287 avg / night
Osprey Suite
1 Bedroom | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

$348 avg / night
Pelican Suite
1 Bedroom | 1 Bath | Sleeps 4

Pelican Suite - Key West, FL

$383 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$280 avg / night
Sunrise Suites - Tierra Bomba Suite 403
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Tierra Bomba Suite 403 - Key West, FL

$416 avg / night

View 373 more homes

Recent Florida Keys guest reviews

Place was great. Perfect location
William M. | May 2024
The location was perfect. We rented bikes through Eaton and the location of the apartment was within a short walk or bike ride. Having a parking space was such an amenity in that area as well. The place itself was cute and clean. We loved the shower and the sitting room.
Erica M. | May 2024
Downhome Cabin was perfect for us. It was spotlessly clean and very comfortable. It had a bright and cheerful interior The kitchen was very well equipped with plenty of dishes and pots and pans. The yard was neat and clean and the docking spot was very well done. We have stayed at several places in the Keys and this was the best. Vacasa did a good job of simplifying check in.
D G. | May 2024
Florida Keys vacation rental FAQ

Yes, 151 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. 376 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 do I find Weekly Vacation Rentals in the Florida Keys?

Right here. We offer a well-curated selection of weekly vacation rentals throughout the Florida Keys. We recommend exploring your options for weekly rentals in the Florida Keys to find the accommodations and community that match your getaway, including destinations like:

Explore weekly rentals in the Florida Keys >

Does Vacasa offer snowbird or long-term rentals in the Florida Keys?

Live like Ernest Hemingway. Like our weekly rentals, we offer a variety of different snowbird rentals in the Florida Keys to choose from, including beachfront cottages surrounded by palm trees, places to stay near The Key West Butterfly and Nature Conservatory, homes with private pools, pet-friendly rentals in Florida, and so much more. Explore the list of snowbird rentals by community for added inspiration:

We offer a wealth of other snowbird rentals in the Florida Keys in communities beyond those, so we recommend exploring all of our offerings to find the ideal long-term lodging.

Explore all snowbird rentals in the Florida Keys >

What can I do at a Florida Keys vacation rental?

With a storied history and lively beach life, there's something for everyone in the Florida Keys. 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.

You can go your speed when staying at a beach house rental or a condo on the Florida Keys coast. Here are a few articles our travel writers provided to inspire our guests:

Explore or Florida Keys vacation rentals

Immerse yourself in the rich history, flavorful local cuisine, and bountiful fishing opportunities that make the Keys a destination like no other place. To simplify your search, explore the accommodations below to find the Florida Keys vacation home rental matching your needs.

You can also skip the filters and explore all of your vacation rental choices to find the ideal beach house for your next getaway as well.

Explore all Florida Keys vacation rentals >