Middle Keys, FL Vacation Rentals

Compare 138 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 71 House rentals
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Duplexes

View 31 Duplexes
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Condo rentals

View 21 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
Coastal Bliss Villa 7080
3 Bed | 3 Bath | Sleeps 8

Coastal Bliss Villa 7080 - Duck Key, FL

$753 avg / night
5.0 (1)
The Tropical Cove 329
1 Bed | 1 Bath | Sleeps 6

The Tropical Cove 329 - Marathon, FL

$306 avg / night
Sombrero Siesta
1 Bed | 1 Bath | Sleeps 4

Sombrero Siesta - Marathon, FL

$367 avg / night
4.28 (39)
Angelfish Inlet #404
1 Bed | 1 Bath | Sleeps 4

Angelfish Inlet #404 - Marathon, FL

$329 avg / night
4.32 (19)
Harbor Villa 7103
2 Bed | 2.5 Bath | Sleeps 6

Harbor Villa 7103 - Duck Key, FL

$483 avg / night
4.56 (36)

View 133 more homes

Recent Middle Keys, FL vacation rental reviews

Loved it. The best stay ever. Beautiful place. All the amenities. Close to great restaurants and beaches. Highly recommended
Maggie A. | Mar 2025
Loved the area. Quiet, friendly, convenient to getting anywhere. The rental was great. Had everything we needed. Even beach towels. Loved the patio and screened porch when it got too hot for us. Cabana Club was a nice plus. Went swimming in the pool and on the beach almost every day. Tuesday Farmer's Market was nice and a big plus also.
Peggy F. | Mar 2025
Nice, clean home, well equipped kitchen. Enjoyed time around pool and screened in porch. We will be back.
Eileen P. | Mar 2025
Middle Keys, FL Frequently Asked Questions

Yes, 46 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. 137 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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