Middle Keys, FL Vacation Rentals

Compare 144 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 79 House rentals
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Duplexes

View 30 Duplexes
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Condo rentals

View 21 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

$396 avg / night
3.95 (110)
C est la Vie Villa 5095
2 Bedroom | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$351 avg / night
4.84 (19)
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$439 avg / night
4.3 (139)
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$355 avg / night
4.3 (23)
A Little Piece of Paradise
1 Bedroom | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$227 avg / night
4.43 (21)

View 139 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

Just what we were looking for. Right by the water. We could watch the sun set from the balconies or living room or kitchen! We based ourselves here and went exploring to the other keys each day. Good central location for us.
Melissa H. | Dec 2024
Perfect location for tours in the middle keys. Near sombrero beach. Very quiet
Christine Z. | Dec 2024
Absolutely gorgeous home and setting. Duck Key is a beautiful island and is in a great location with easy access to amenities and adventures. We had a great stay here!
Julie W. | Dec 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. 143 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   |   Lower Keys, FL   |   Coco Plum Beach - Marathon   |   Fat Deer Key - Key Colony Beach   |   Skipjack Resort & Marina - Marathon, FL   |   Islamorada   |   Marathon   |   Duck Key   |   Conch Key   |   Long Key   |   Key Colony Beach   |   Florida
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