Middle Keys, FL Vacation Rentals

Compare 139 vacation rentals.
An error was detected and reported for this component.
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

housing_type_house.jpg

House rentals

View 71 House rentals
housing_type_duplex.jpg

Duplexes

View 31 Duplexes
housing_type_condo.jpg

Condo rentals

View 21 Condo rentals

Explore more vacation rental amenities in Middle Keys, FL

Pool | Electric vehicle charger | Ocean view | Oceanfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Coastal Bliss Villa 7080
3 Bed | 3 Bath | Sleeps 8

Coastal Bliss Villa 7080 - Duck Key, FL

$749 avg / night
5.0 (1)
Restful Retreat - Villa 5067
2 Bed | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$421 avg / night
4.44 (48)
Sombrero Siesta
1 Bed | 1 Bath | Sleeps 4

Sombrero Siesta - Marathon, FL

$363 avg / night
4.28 (39)
Palm Villa - Villa 5115
2 Bed | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$577 avg / night
4.29 (146)
A Little Piece of Paradise
1 Bed | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$284 avg / night
4.39 (23)

View 134 more homes

Recent Middle Keys, FL vacation rental reviews

We had a fabulous stay at La Pirata. It is a clean, well stocked home in a great location. There was plenty of dock space for a 30ft boat with extra room for fishing. We would book again.
Carla C. | Mar 2025
Nice and cozy
Maribel G. | Mar 2025
Perfect 'home-base' for our Keys vacation!
Karen T. | Mar 2025
Middle Keys, FL Frequently Asked Questions

Yes, 46 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. 138 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

People also search for

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Everglades National Park   |   Lower Keys, FL   |   Coco Plum Beach - Marathon   |   Fat Deer Key - Key Colony Beach   |   Skipjack Resort & Marina - Marathon, FL   |   Islamorada   |   Key Colony Beach   |   Long Key   |   Conch Key   |   Marathon   |   Duck Key   |   Florida
Show more