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 75 House rentals
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Duplexes

View 30 Duplexes
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Condo rentals

View 19 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Fisherman's Bungalow
0 Bedroom | 1 Bath | Sleeps 4

Fisherman's Bungalow - Conch Key, FL

$184 avg / night
3.44 (9)
Restful Retreat - Villa 5067
2 Bedroom | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$355 avg / night
4.43 (47)
Sombrero Siesta
1 Bedroom | 1 Bath | Sleeps 4

Sombrero Siesta - Marathon, FL

$286 avg / night
4.22 (36)
Harbor Hideaway Villa 7066
4 Bedroom | 3 Bath | Sleeps 8

Harbor Hideaway Villa 7066 - Duck Key, FL

$537 avg / night
4.62 (8)
The Coconut Cottage Villa 5070
2 Bedroom | 2 Bath | Sleeps 6

The Coconut Cottage Villa 5070 - Duck Key, FL

$334 avg / night
4.0 (21)

View 133 more homes

Browse more vacation rental amenities in Middle Keys, FL

Pool | Electric vehicle charger | Ocean view | Oceanfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator

Recent Middle Keys, FL guest reviews

House was very nice, updated and clean. Everything worked smoothly. Outside/backyard living was beautiful. Lots of outdoor amenities and access to canal/ocean was a lot of fun.
daniel w. | Jan 2025
Excellent outdoor area, as described. Wonderful vacation in Marathon. Loved watching the airplanes from the back porch.
jason d. | Jan 2025
Great cottage for small family
Scott B. | Jan 2025
Middle Keys, FL vacation rental FAQ

Yes, 49 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Everglades National Park   |   Lower Keys, FL   |   Coco Plum Beach - Marathon   |   Fat Deer Key - Key Colony Beach   |   Skipjack Resort & Marina - Marathon, FL   |   Duck Key   |   Marathon   |   Islamorada   |   Key Colony Beach   |   Long Key   |   Conch Key   |   Florida
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