Middle Keys, FL Vacation Rentals

Compare 133 vacation rentals with savings up to 30% off this summer.
USA > Florida > Middle Keys, FL

Make Middle Keys, FL your next getaway

Explore our vacation rentals on Middle Keys Florida. Our private accommodations include everything you need to have the perfect beach getaway, whether you're here for a family vacation, couples retreat, or making memories with friends.

Explore Middle Keys, FL house rentals, duplexes, condo rentals, and more


House rentals

View 82 House rentals


View 26 Duplexes

Condo rentals

View 12 Condo rentals

Middle Keys, FL vacation rentals for every getaway

Dog-friendly Hot tub Internet
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$295 avg / night
Restful Retreat - Villa 5067
2 Bedroom | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$251 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$233 avg / night
Palm Breeze - Villa 5030
2 Bedroom | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$265 avg / night
Key Lime Villa
2 Bedroom | 2 Bath | Sleeps 6

Key Lime Villa - Duck Key, FL

$296 avg / night

View 128 more homes

Recent Middle Keys, FL vacation rental reviews

We loved everything about this rental property, the cleanliness, view, furnishings, amenities, ease of booking etc. the owners really believe in taking care of their guests.
Cheryl R. | May 2023
This house is spectacular! I went with my wife and kids and the home is beautiful inside with all new furrniture and appliances!!! It also has an amazing view of the ocean and plenty of parking… They have great kayaks and I took the kids for a quick adventure on the canals from the house. Also, we had our boat and home is fully equipped for fishing with large ice machine, freezer, fish cleaning table and 50ft dock. Can’t say enough great things about this place, definitely coming back!
Rafael C. | May 2023
We loved our stay here. Everything we could think of was here, except for grilling utensils. Perfect place for all of us (6). Everyone was nice, we biked to the beach both private and public just a short distance. The last day we were there the residents that live in the neighborhood were at the private beach and they actually swim here and snorkel. If you want to snorkel the Sombrero Reef we would suggest Captain Pips, they are excellent.
SABRINA M. | May 2023
Middle Keys, FL vacation rental FAQ

Yes, 43 of our Middle Keys, FL 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. 132 of our Middle Keys, FL 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 Middle Keys, FL 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 Middle Keys, FL 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 Middle Keys, FL, 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