Middle Keys, FL Vacation Rentals

Compare 161 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 86 House rentals
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Duplexes

View 30 Duplexes
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Condo rentals

View 25 Condo rentals

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Palm Breeze - Villa 5030
2 Bedroom | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$240 avg / night
C est la Vie Villa 5095
2 Bedroom | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$248 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$278 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$214 avg / night
A Little Piece of Paradise
1 Bedroom | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$191 avg / night

View 156 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 vacation rental reviews

My husband and I stayed here for our honeymoon. The home was absolutely fabulous and super clean. The outside at night was spectacular and it truly felt like our own oasis. The home is on a quiet street with sweet neighbors as well. We already said we will be back next year!
Jamie R. | Apr 2024
Lovely view. Super clean.
Lauren J. | Apr 2024
Beautiful facilities and so clean and new. Great location, so quiet and private. Fully equipped kitchen with great appliances. Great dock from which to launch kayaks. Ten minutes cycle ride to beach, thirty minutes walk. Would happily rebook.
James S. | Apr 2024
Middle Keys, FL vacation rental FAQ

Yes, 51 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. 160 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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