Middle Keys, FL Vacation Rentals

Compare 136 vacation rentals.
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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 70 House rentals
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Duplexes

View 30 Duplexes
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Condo rentals

View 20 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Blue Water Cottage Villa 5110
2 Bedroom | 1.5 Bath | Sleeps 6

Blue Water Cottage Villa 5110 - Duck Key, FL

$273 avg / night
Palm Breeze - Villa 5030
2 Bedroom | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$355 avg / night
3.96 (115)
Coastal Bliss Villa 7080
3 Bedroom | 3 Bath | Sleeps 8

Coastal Bliss Villa 7080 - Duck Key, FL

$524 avg / night
5.0 (2)
Restful Retreat - Villa 5067
2 Bedroom | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$294 avg / night
4.46 (50)
The Tropical Cove 329
1 Bedroom | 1 Bath | Sleeps 6

The Tropical Cove 329 - Marathon, FL

$216 avg / night
5.0 (1)

View 131 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

everything except, dull knives. Was great having a separate fridge for the pool area. Truly exceptional!!!
clinton c. | Apr 2025
We really enjoyed staying here. It was clean, with modern furnishing and even more stunning than in the pictures. Being right on the water was such a treat ... and having two decks that overlooked the water was lovely. We loved it. I texted guest services before checking out and they immediately responded. I would definitely stay here again with my family. It was a treat to be here.
Jaimy G. | Apr 2025
Very clean, convenient. Did not have any spices such as salt and pepper. Would think that is a must.
Elise R. | Apr 2025
Middle Keys, FL vacation rental FAQ

Yes, 47 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. 135 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Middle Keys, FL, log in to Trip Manager to explore the 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   |   Islamorada   |   Marathon   |   Duck Key   |   Key Colony Beach   |   Long Key   |   Conch Key   |   Florida
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