Middle Keys, FL Vacation Rentals

Compare 113 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.

Explore Middle Keys, FL house rentals, duplexes, condo rentals, and more

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House rentals

View 58 House rentals
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Duplexes

View 23 Duplexes
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Condo rentals

View 17 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
Palm Villa - Villa 5115
2 Bed | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$406 avg / night
(excludes fees and taxes)
4.28 (153)
Restful Retreat - Villa 5067
2 Bed | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$275 avg / night
(excludes fees and taxes)
4.48 (58)
The Tropical Cove 329
1 Bed | 1 Bath | Sleeps 4

The Tropical Cove 329 - Marathon, FL

$198 avg / night
(excludes fees and taxes)
4.75 (4)
Palm Breeze - Villa 5030
2 Bed | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$321 avg / night
(excludes fees and taxes)
3.99 (120)
Blue Water Cottage Villa 5110
2 Bed | 1.5 Bath | Sleeps 6

Blue Water Cottage Villa 5110 - Duck Key, FL

$231 avg / night
(excludes fees and taxes)
4.67 (9)

View 108 more homes

Recent Middle Keys, FL vacation rental reviews

Close to everything!
Andrea, D. | Dec 2025
Great
Corvecco P. | Dec 2025
The area and the townhouse
Melissa B. | Dec 2025
Middle Keys, FL Frequently Asked Questions

Yes, 38 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. 112 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

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