Florida Keys Vacation Rentals

Compare 356 vacation rentals. Enter your trip dates to get started.
USA > Florida > Florida Keys

Make Florida Keys your next getaway—choose from 356 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 175 House rentals
housing_type_condo.jpg

Condo rentals

View 98 Condo rentals
housing_type_duplex.jpg

Duplexes

View 28 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

$506 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$347 avg / night
Palm Breeze - Villa 5030
2 Bedroom | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$310 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$272 avg / night
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$238 avg / night

View 351 more homes

Recent Florida Keys vacation rental reviews

This home is very well appointed, and we thoroughly enjoyed our stay. We are property owners and managers ourselves in Surfside Beach, SC, and we've been in the business for over 15 years, so we have set expectations for cleanliness and comfort, which were all met - kitchen is well appointed with high end appliances, and I enjoyed having the extra room upstairs to use as my working office. The location is excellent, in the Meadows, a very nice residential area, and we were able to walk or bike to everything. The heated salt water pool was also great, and the nice, private yard was a treat to sit and enjoy morning coffee, etc.
Jennifer O. | Feb 2023
This place was amazing. I wish we had more than just two nights here! The place was a perfect location and very very clean. It was actually more spacious than I expected and the deck was perfect for people watching and coffee!
Chanda M. | Feb 2023
The full kitchen was well stocked for up to 6 people with essential pots, pans, utensils, glasses, plates, coffeemaker, oven and toaster. Good size refrigerator. The pool and hot tub are nice. You need to drive or get transportation to downtown Key West. It was nice and quiet .
Kathleen G. | Feb 2023
Florida Keys vacation rental FAQ

Yes, 146 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. 355 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.