Florida Keys Vacation Rentals

Compare 288 vacation rentals. Enter your trip dates to get started.
USA > Florida > Florida Keys

Make Florida Keys your next getaway—choose from 288 great Florida Keys 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, studios, and more

housing_type_house.jpg

House rentals

View 102 House rentals
housing_type_condo.jpg

Condo rentals

View 94 Condo rentals
housing_type_studio.jpg

Studios

View 33 Studios

Florida Keys vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Cool Breeze 3D Tour
2 Bed | 2.5 Bath | Sleeps 6

Cool Breeze - Key West, FL

From $313
Canalside Cabana 3D Tour
4 Bed | 3 Bath | Sleeps 10

Canalside Cabana - Marathon, FL

From $397
Sombrero Siesta Retreat
4 Bed | 3 Bath | Sleeps 10

Sombrero Siesta Retreat - Marathon, FL

From $417
Conch Cottage 3D Tour
1 Bed | 1 Bath | Sleeps 5

Conch Cottage - Key West, FL

From $221
Bright Key West Beauty 3D Tour
2 Bed | 2.5 Bath | Sleeps 5

Bright Key West Beauty - Key West, FL

From $257

View 283 more homes

Recent Florida Keys vacation rental reviews

we liked the location. It wasn't too far to walk to most attractions and dining.
Jeff P. | Jan 2021
Very nicely appointed Condo. Nice two bedroom, two bath. Nice balcony overlooking the pool. The couch has seen better days, but’s that minor. Would stay in this unit again.
Neil S. | Jan 2021
We loved our stay at the Egret suite on Simonton. it is, however, a main road and can get pretty loud with trucks coming in and out just outside your door. There is a liquor store across the street that looks fun, called the tipsy rooster, but also is loud throughout the day. The Casa checked on her several times during our stay and we had everything that we needed.
Anne K. | Jan 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