Middle Keys, FL Vacation Rentals

Compare 164 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

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House rentals

View 85 House rentals
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Duplexes

View 31 Duplexes
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Condo rentals

View 28 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

$286 avg / night
C est la Vie Villa 5095
2 Bedroom | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$264 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$322 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$250 avg / night
A Little Piece of Paradise
1 Bedroom | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$175 avg / night

View 159 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

Sheltered from the East winds. Calm cove to paddle around in the kayaks. With a deck to sit and watch the sunset.
William M. | May 2024
We spent the days fishing out on our boat or lounging at the pool and evenings watching playoff hockey and having drinks. We enjoyed the outside bar and TV. The house needs some new pool floats and pool sticks but we made do with what was there.
Ellen S. | Apr 2024
Great water front cute little townhome, very clean and comfortable. Beds were great, all furniture in perfect condition, full kitchen. Beautiful view, mid way from the continent to Key west and still not too far that you are able to enjoy all the activities without being in the busy roads all the time, so you are able to also get some peace and quiet if you want. We'll sure go back.
Marissis G. | Apr 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. 162 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

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   |   Duck Key   |   Marathon   |   Key Colony Beach   |   Long Key   |   Conch Key   |   Florida
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