Middle Keys, FL Vacation Rentals

Compare 101 vacation rentals.
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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.

Top Middle Keys, FL property types

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House rentals

View 73 House rentals
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Condo rentals

View 14 Condo rentals
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Townhouses

View 7 Townhouses

Popular amenities for Middle Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Gold Starfish
2 Bedroom | 2.5 Bath | Sleeps 4

Gold Starfish - Marathon, FL

$370 avg / night
(excludes fees and taxes)
4.5 (6)
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$487 avg / night
(excludes fees and taxes)
4.26 (157)
Gray Pelican House
2 Bedroom | 2 Bath | Sleeps 6

Gray Pelican House - Key Colony Beach, FL

$260 avg / night
(excludes fees and taxes)
5.0 (1)
Jewel in the Sea Villa 5080
2 Bedroom | 1.5 Bath | Sleeps 6

Jewel in the Sea Villa 5080 - Duck Key, FL

$496 avg / night
(excludes fees and taxes)
2.75 (4)
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$395 avg / night
(excludes fees and taxes)
4.33 (40)

View 96 more homes

Browse more vacation rental amenities in Middle Keys, FL

Pool | Electric vehicle charger | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Fireplace | Washer/dryer

Recent Middle Keys, FL guest reviews

Very clean, great interior decor, everything worked! Couldn't ask for more...
Mark T. | Apr 2026
Thank you for providing such a wonderful environment for our recent vacation. We thoroughly enjoyed our stay at your Key West property and appreciated the variety of activities available throughout our trip. Despite the changes in weather, we were still able to enjoy snorkeling and utilize the canoe to visit the island. The property's proximity to the airport also made our travel logistics very convenient. We appreciate your hospitality and the excellent experience.
Erin A. | Apr 2026
We love everything about the home. We had 3 couples and space for everyone. All the activities available made it even better. We spent 90% of our time just at the house and it was great. The view is spectacular!
Roxanne H. | Apr 2026
Middle Keys, FL vacation rental FAQ

Yes, 36 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. 101 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Middle Keys, FL, log in to Trip Manager to explore the 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   |   Key Colony Beach   |   Conch Key   |   Long Key   |   Marathon   |   Islamorada   |   Layton   |   Duck Key   |   Florida
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