Florida Keys Vacation Rentals

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Make Florida Keys your next getaway—choose from 296 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.

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House rentals

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Condo rentals

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Florida Keys vacation rentals for every getaway

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

Cool Breeze - Key West, FL

From $313
Sombrero Siesta Retreat
4 Bed | 3 Bath | Sleeps 10

Sombrero Siesta Retreat - Marathon, FL

From $363
Conch Cottage 3D Tour
1 Bed | 1 Bath | Sleeps 5

Conch Cottage - Key West, FL

From $232
Tropical Village - Hideaway 3D Tour
2 Bed | 1 Bath | Sleeps 6

Tropical Village - Hideaway - Key West, FL

From $263
Plein Air Point 3D Tour
3 Bed | 2 Bath | Sleeps 8

Plein Air Point - Marathon, FL

From $506

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Recent Florida Keys vacation rental reviews

Close to Sombrero Beach by car and kayak! Groceries close by allow for maximum relaxation time. We stayed with our 4 kids and there was room to gather and grill and room to spread out for down time. Very nice home and highly recommend!
Jennifer M. | Apr 2021
Our family loved our stay at this vacation home. The house itself had everything we needed for comfort, cooking and enjoyment. Being on the channel that connects to a lovely little bay with smaller keys was a hidden treasure. We flew our inflatable paddle boards down and spent many afternoons paddling around the small bay and snorkeling around the small little keys. Very fun snorkeling! We biked to Sombrero beach (about 4 miles). But really, with the pool and paddling had plenty to fill the sunny days. We'd highly recommend this cute vacation home.
Sara F. | Apr 2021
Centrally located to everything in Old Town. We rented a cart for several days so the parking spot did come in handy. Pool was clean and lounge chairs are comfortable. Full kitchen is nice. Rooms are small but all that you need. We will definitely be back.
Andy O. | Apr 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

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Plan your Florida Keys snorkeling vacation