Florida Keys Vacation Rentals

Compare 319 vacation rentals. Enter your trip dates to get started.
USA > Florida > Florida Keys

Make Florida Keys your next getaway—choose from 319 great vacation rentals

Delightfully warm weather, 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 123 House rentals
housing_type_condo.jpg

Condo rentals

View 92 Condo rentals
housing_type_duplex.jpg

Duplexes

View 33 Duplexes

Florida Keys vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Papa's Hideaway #4 - Islands in the Stream 3D Tour
0 Bed | 1 Bath | Sleeps 4

Papa's Hideaway #4 - Islands in the Stream - Key West, FL

From $206
Azure Breeze 3D Tour
2 Bed | 2 Bath | Sleeps 6

Azure Breeze - Duck Key, FL

From $148
Restful Retreat 3D Tour
2 Bed | 1.5 Bath | Sleeps 6

Restful Retreat - Duck Key, FL

From $152
Island Paradise 3D Tour
3 Bed | 3.5 Bath | Sleeps 6

Island Paradise - Key West, FL

From $249
Duck Key Getaway
3 Bed | 2.5 Bath | Sleeps 8

Duck Key Getaway - Duck Key, FL

From $272

View 314 more homes

Recent Florida Keys vacation rental reviews

The location is perfect. In the middle of everything. Just off Duval, up the street from the Hemingway museum, everything less than a mile away. Great layout of two cottages. Four total bedrooms, 2 bathrooms. Nice separation if needed. Only drawback was heat index was 102 and Air Conditioning struggled to keep up. Plus the Hot Tubs need some help, missing a few pieces. Also, two wifi setup, one worked, on didn't. The service was great, anything needed was just a call away, very responsive!
Chip N. | Jul 2021
My family and our six grandchildren vacationed for the week in this vacation house. The house was spacious and the location couldn’t have been better. The entire house was just gorgeous. We would definitely stay in next year! Lots of family memories were made.
Carol B. | Jul 2021
Clean place and close to town. Not walking distance like described but quite. The only thing that we didn’t like was the very poor lighting around elevators down stairs.
Rodney A. | Jul 2021

Book confidently. Stay comfortably.

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


Where are our Florida Keys vacation rentals?

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.

There's more to see on the Overseas Highway than just Key West, though. Key Largo's snorkeling, Little Conch Key's laid-back attitude, and the sea turtle hospital in Marathon are just a taste of your Florida Keys options.

Getting out on the open water is the heart and soul of the Keys. Both experienced sailors striking out on their own and beginners going out under the supervision of a captain will love the bright blue Caribbean waves. Anglers will want to bring along their fishing gear and catch something for dinner. Anyone wanting some excitement can try other aquatic adventures, like scuba diving and parasailing.

There are plenty of land-based options as well, like visiting the preserved mango swamps of Marathon or learning about dolphins at the Dolphin Research Center. Or, go back to basics and spend time soaking up the sun on the beach.

Heading to our Florida Keys vacation rentals is an ideal choice for someone looking to get away from the daily grind. After a few days in your Florida Keys beach house rental, you'll wish you could stay forever.

Discover the Florida Keys

4 Florida Keys Races and Marathons for Every Skill Level
The Ultimate Escape: Key West Cottages with Private Pools
Plan your Florida Keys snorkeling vacation