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
Jewel in the Sea Villa 5080
2 Bed | 1.5 Bath | Sleeps 6

Jewel in the Sea Villa 5080 - Duck Key, FL

$401 avg / night
(excludes fees and taxes)
1.0 (1)
Sea Grape Getaway
0 Bed | 1 Bath | Sleeps 2

Sea Grape Getaway - Marathon, FL

$170 avg / night
(excludes fees and taxes)
4.86 (7)
Seaside Manor
4 Bed | 2 Bath | Sleeps 10

Seaside Manor - Marathon, FL

$465 avg / night
(excludes fees and taxes)
4.5 (2)
Key Lime Villa
2 Bed | 2 Bath | Sleeps 6

Key Lime Villa - Duck Key, FL

$348 avg / night
(excludes fees and taxes)
4.74 (35)
Harbor Hideaway Villa 7066
4 Bed | 3 Bath | Sleeps 8

Harbor Hideaway Villa 7066 - Duck Key, FL

$560 avg / night
(excludes fees and taxes)
4.73 (22)

View 108 more homes

Recent Middle Keys, FL vacation rental reviews

The house is absolutely beautiful . We r joyed every minute of our time spent there. The pool was warm and amazing we used it everyday. The house layout was great and everything we needed was there. We will definitely stay there again !!!
Stephanie W. | Feb 2026
We loved it here! Everything is so convenient. We will definitely be back
Linda N. | Feb 2026
We stay for the month of January this year, and found it to be very comfortable to live in. The unit had lots of space, it was very clean, the kitchen was well equipped, but best of all was the pool area. We spent most of our time around the pool area and at the table where we played many games and enjoyed dining there. You will not be disappointed staying here. In fact, we’ve booked it already for next year. If you’re driving here, consider bringing a leaf blower. I brought my blower and used it often.
John A. | Feb 2026
Middle Keys, FL Frequently Asked Questions

Yes, 37 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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