Middle Keys, FL Vacation Rentals

Compare 163 vacation rentals.
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 85 House rentals


View 31 Duplexes

Condo rentals

View 27 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

Dog-friendly Hot tub Internet
Palm Breeze - Villa 5030
2 Bedroom | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$367 avg / night
C est la Vie Villa 5095
2 Bedroom | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$269 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$376 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$311 avg / night
A Little Piece of Paradise
1 Bedroom | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$191 avg / night

View 158 more homes

Recent Middle Keys, FL guest reviews

The cleanliness of the apartment and the entire environment was outstanding. A very quaint place for a beautiful vacation. It was just an awesome experience.
Richard K. | May 2024
Downhome Cabin was perfect for us. It was spotlessly clean and very comfortable. It had a bright and cheerful interior The kitchen was very well equipped with plenty of dishes and pots and pans. The yard was neat and clean and the docking spot was very well done. We have stayed at several places in the Keys and this was the best. Vacasa did a good job of simplifying check in.
D G. | May 2024
We had a wonderful time! It was fantastic to have a pool all to ourselves! The house was clean and having a washer and dryer was very convenient. The location was also great! We would stay here again!
Ashley S. | May 2024
Middle Keys, FL vacation rental FAQ

Yes, 51 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. 161 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