Florida Keys Vacation Home Rentals

Compare 304 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 155 House rentals
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Condo rentals

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Duplexes

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Popular amenities for Florida Keys vacation rentals

Popular
Dog-friendly Hot tub Internet
Windward Isle
2 Bedroom | 1 Bath | Sleeps 6

Windward Isle - Key West, FL

$630 avg / night
4.32 (41)
Truman @ Duval - Unit F
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit F - Key West, FL

$342 avg / night
4.23 (31)
Sunrise Suites - Barbados Suite 204
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Barbados Suite 204 - Key West, FL

$511 avg / night
4.2 (132)
Sunrise Suites - Panama Suite 310
2 Bedroom | 2 Bath | Sleeps 6

Sunrise Suites - Panama Suite 310 - Key West, FL

$445 avg / night
4.53 (133)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$365 avg / night
4.4 (48)

View 299 more homes

Recent Florida Keys guest reviews

Just finished a quick stay, and enjoyed everything. Love the access to Duval Street. They’ve done a great job with the house and we plan to stay again but longer this time.
Kevin C. | Jan 2025
The house location is the best. The house and Pool! The views. The amenities. The pool heater! Sunrise and sunset. Privacy and semi seclusion. Nearby access to any and everything you could need or want to do in the keys! Cant say enough good things! This stay has started a life long journey with the florida keys!
J H. | Jan 2025
What a wonderful spot for a couple to spend their downtime to recharge while out and about in Key West. It was a perfect spot to take a nap, whip up a meal, or just relax in the A/C while reading a book. This property sits back with a private, gated entry which makes it feel more secluded and private. Wonderful spot for two to enjoy their time together.
James F. | Jan 2025
Florida Keys vacation rental FAQ

Yes, 114 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. 303 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
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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 >