Middle Keys, FL Vacation Rentals

Compare 91 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, condo rentals, townhouses, and more

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House rentals

View 65 House rentals
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Condo rentals

View 12 Condo rentals
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Townhouses

View 8 Townhouses

Explore more vacation rental amenities in Middle Keys, FL

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

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
MA132 - Hook Line & Sunset
2 Bed | 2 Bath | Sleeps 6

MA132 - Hook Line & Sunset - Marathon, FL

$384 avg / night
(excludes fees and taxes)
4.76 (25)
KC100 - Breezy Keys
4 Bed | 2 Bath | Sleeps 8

KC100 - Breezy Keys - Key Colony Beach, FL

$542 avg / night
(excludes fees and taxes)
5.0 (4)
KC111 - Gray Pelican House
2 Bed | 2 Bath | Sleeps 6

KC111 - Gray Pelican House - Key Colony Beach, FL

$341 avg / night
(excludes fees and taxes)
5.0 (2)
MA127 - Marathon Majesty
3 Bed | 2 Bath | Sleeps 8

MA127 - Marathon Majesty - Marathon, FL

$766 avg / night
(excludes fees and taxes)
4.57 (28)
MA68 - Plein Air Point
3 Bed | 2 Bath | Sleeps 8

MA68 - Plein Air Point - Marathon, FL

$960 avg / night
(excludes fees and taxes)
4.92 (90)

View 86 more homes

Recent Middle Keys, FL vacation rental reviews

We had a great stay with our family. The house was very clean and the amenities provided made sure we had everything that we needed. It was great to have beach chairs and beach toys for the kids.
Jennifer D. | Jul 2026
We loved the location and the home.
Sarah W. | Apr 2026
We spent a lovely week here with our granddaughter. The neighbors made it feel like home. The pool (apparently the largest in the keys) was a highlight. We utilized the community BBQ a couple of times to make dinner. Marathon is a great location for a home base. We would stay here again!
Kim W. | Apr 2026
Middle Keys, FL Frequently Asked Questions

Yes, 32 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. 91 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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