Middle Keys, FL Vacation Rentals

Compare 163 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 85 House rentals
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Duplexes

View 31 Duplexes
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Condo rentals

View 27 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

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

Palm Breeze - Villa 5030 - Duck Key, FL

$287 avg / night
C est la Vie Villa 5095
2 Bedroom | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$266 avg / night
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$328 avg / night
Duck Key Retreat Villa #5105
2 Bedroom | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$252 avg / night
A Little Piece of Paradise
1 Bedroom | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$171 avg / night

View 158 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 guest reviews

We loved the location and development. The apartment is very well supplied. The apartment is very nice, has a comfy bed, and has some good fishing in the marina.
Smith T. | May 2024
We thoroughly enjoyed our stay! So comfortable and light and airy! We wanted for nothing! The views are amazing, we spent much of our time on the balcony relaxing and gazing out onto the gorgeous property! Everything was clean lovely and well appointed! Can’t wait to go back!
Sue K. | May 2024
We have frequented the Florida Keys for many years now and this was our first time staying in Duck Key at this property with Vacasa. The entire experience overall was great. Booking was easy, instructions were clear and sent over timely as were text messages before and during our stay. The property is located in a convenient location with a short drive to Marathon. The house itself is well appointed and was very clean. The kitchen is big enough to cook full meals and the living room and dining room were perfect for relaxing. The small splash pool was fun for relaxing and refreshing after a long day exploring. The location was quiet and we had no problems with parking. Overall, the entire experience was great. 5 stars.
Charles S. | May 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. 161 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

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   |   Islamorada   |   Marathon   |   Duck Key   |   Key Colony Beach   |   Long Key   |   Conch Key   |   Florida
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