Florida Keys Vacation Rentals

Compare 350 vacation rentals. Enter your trip dates to get started.
USA > Florida > Florida Keys

Make Florida Keys your next getaway—choose from 350 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

housing_type_house.jpg

House rentals

View 170 House rentals
housing_type_condo.jpg

Condo rentals

View 98 Condo rentals
housing_type_duplex.jpg

Duplexes

View 27 Duplexes

Florida Keys vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Overseas Oasis
3 Bedroom | 2.5 Bath | Sleeps 6

Overseas Oasis - Key Largo, FL

$554 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$354 avg / night
Palm Breeze - Villa 5030
2 Bedroom | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$307 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$291 avg / night
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$267 avg / night

View 345 more homes

Recent Florida Keys vacation rental reviews

This rental was walking distance from SO MUCH and still far enough from Duval Street that there was peace and quiet! The property was clean and just big enough to be comfortable without taking anything away.
Gretchen L. | Sep 2022
We had a wonderful visit. This home is clean, quiet and well equipped. It was very close to everything we wanted to do while in Key West. I suggest renting bikes and exploring and visiting the beach at Fort Zachary state park. We had a restful week on the island and look forward to returning.
Laura S. | Sep 2022
Our family enjoyed this home immensely! All of the beds were comfortable, the bathrooms worked for tall people, the kitchen had everything we needed and the big sofa housed us all. Outside, the pool area, under deck living area and kayaks were all that we needed. Thanks for a wonderful and relaxing stay.
Tim B. | Sep 2022
Florida Keys Frequently Asked Questions

Yes, 143 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. 349 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.