Middle Keys, FL Vacation Rentals

Compare 159 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 33 Duplexes
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Condo rentals

View 23 Condo rentals

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Angler's Escape
2 Bed | 2 Bath | Sleeps 6

Angler's Escape - Marathon, FL

$494 avg / night
Cheeseburger Paradise
4 Bed | 2 Bath | Sleeps 8

Cheeseburger Paradise - Marathon, FL

$497 avg / night
Angelfish Inlet #404
1 Bed | 1 Bath | Sleeps 4

Angelfish Inlet #404 - Marathon, FL

$276 avg / night
Palm Villa - Villa 5115
2 Bed | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$394 avg / night
Restful Retreat - Villa 5067
2 Bed | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$335 avg / night

View 154 more homes

Recent Middle Keys, FL vacation rental reviews

The home was everything promised. The location on the Key was perfect. The home was so spacious and well maintained. While small, the pool was delightful to just relax in. We will be back!
Pamela P. | Feb 2024
Having two separate houses to join was so fun and perfect for our week long stay. Walking distance to playground and the dock for the boat was so convenient. Since the kitchens were fully equipped we easily made family meals to save on the expense of eating out every meal. The location being close to Marathon is convenient to get to anything you need.
Arthur J. | Feb 2024
This house has everything you can want. The group of manatess coming to enjoy a freshwater splash from the hose was my favorite part.
Kacy M. | Feb 2024
Middle Keys, FL Frequently Asked Questions

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. 158 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