Middle Keys, FL Vacation Rentals

Compare 106 vacation rentals.
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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, condo rentals, townhouses, and more

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House rentals

View 75 House rentals
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Condo rentals

View 16 Condo rentals
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Townhouses

View 8 Townhouses

Explore more vacation rental amenities in Middle Keys, FL

Pool | Electric vehicle charger | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Fireplace | Washer/dryer

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Keys Therapy
2 Bed | 2.5 Bath | Sleeps 6

Keys Therapy - Marathon, FL

$398 avg / night
(excludes fees and taxes)
The Mermaid's Retreat
1 Bed | 2 Bath | Sleeps 4

The Mermaid's Retreat - Marathon, FL

$323 avg / night
(excludes fees and taxes)
4.78 (18)
Yellowtail House
2 Bed | 2 Bath | Sleeps 6

Yellowtail House - Marathon, FL

$390 avg / night
(excludes fees and taxes)
4.85 (13)
Fisherman's Retreat
0 Bed | 2 Bath | Sleeps 8

Fisherman's Retreat - Conch Key, FL

$508 avg / night
(excludes fees and taxes)
4.67 (3)
Isla Bella Villa
2 Bed | 2 Bath | Sleeps 6

Isla Bella Villa - Marathon, FL

$576 avg / night
(excludes fees and taxes)
2.75 (4)

View 101 more homes

Recent Middle Keys, FL vacation rental reviews

Thank you for providing such a wonderful environment for our recent vacation. We thoroughly enjoyed our stay at your Key West property and appreciated the variety of activities available throughout our trip. Despite the changes in weather, we were still able to enjoy snorkeling and utilize the canoe to visit the island. The property's proximity to the airport also made our travel logistics very convenient. We appreciate your hospitality and the excellent experience.
Erin A. | Apr 2026
Very clean, great interior decor, everything worked! Couldn't ask for more...
Mark T. | Apr 2026
We loved the location and the view of the ocean. The resort was quiet, clean and well kept. A little more attention to cleaning the floor would be good.
Greg G. | Apr 2026
Middle Keys, FL Frequently Asked Questions

Yes, 36 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. 106 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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