Middle Keys, FL Vacation Rentals

Compare 153 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

housing_type_house.jpg

House rentals

View 82 House rentals
housing_type_duplex.jpg

Duplexes

View 30 Duplexes
housing_type_condo.jpg

Condo rentals

View 23 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

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

Palm Breeze - Villa 5030 - Duck Key, FL

$321 avg / night
C est la Vie Villa 5095
2 Bedroom | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$240 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$367 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$284 avg / night
A Little Piece of Paradise
1 Bedroom | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$150 avg / night

View 148 more homes

Browse more vacation rental amenities in Middle Keys, FL

Pool | Ocean view | Oceanfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator | Fireplace

Recent Middle Keys, FL guest reviews

Very nice place, close to food and shopping. Loved the pool and beach located across the road.
Chris M. | Jul 2024
We loved the condo! And the location cannot be beat. The beach access is private with plenty of lounge chairs. The pool was wonderful and always clean. The property is quiet and family oriented. One of our favorite meals was had at Burdines (order the fries with garlic aioli!). The key lime pie is amazing too! There’s a little Mexican restaurant right up the road from the condo- authentic and delicious!
Molly S. | Jul 2024
I as a Hostess of Airbnb myself am very critical when staying at others, but this home was over the top everything was on point from the cleanliness to the well appointed kitchen,abundance amounts of pool & bath towels as there were 8 of us. Deep Water access to Gulf & Atlantic very convenient, only recommendtions would be to improve bumper guards at the dock & boat cleats would make coming in easier.,luckily my son had bought his own fenders plus extra’s.PS we did have the upstairs AC stop working issue was resolved w in 2 hours bad thermostat . I give this Home Ten Stars Plus
Linda R. | Jul 2024
Middle Keys, FL vacation rental FAQ

Yes, 52 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. 150 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

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