Middle Keys, FL Vacation Rentals

Compare 147 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 80 House rentals
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Duplexes

View 30 Duplexes
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Condo rentals

View 21 Condo rentals

Explore more vacation rental amenities in Middle Keys, FL

Pool | Ocean view | Oceanfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator | Fireplace

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Palm Breeze - Villa 5030
2 Bed | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$478 avg / night
3.94 (108)
C est la Vie Villa 5095
2 Bed | 2.5 Bath | Sleeps 6

C est la Vie Villa 5095 - Duck Key, FL

$446 avg / night
4.84 (19)
Palm Villa - Villa 5115
2 Bed | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$536 avg / night
4.3 (135)
Duck Key Retreat Villa #5105
2 Bed | 1.5 Bath | Sleeps 6

Duck Key Retreat Villa #5105 - Duck Key, FL

$437 avg / night
4.3 (23)
A Little Piece of Paradise
1 Bed | 1 Bath | Sleeps 3

A Little Piece of Paradise - Marathon, FL

$278 avg / night
4.42 (19)

View 142 more homes

Recent Middle Keys, FL vacation rental reviews

The place was very clean and had a lovely upper and lower deck to enjoy coffee and cocktails on. The bed was pretty comfy as well. Please note, the sunset view is obstructed by a marina building and there are no beach chairs or gear to borrow while you're there. There was plenty of soap, shampoo, dishwasher detergent etc. There was no laundry soap if you'd like to do a load or two but we came prepared with laundry detergent sheets.
AISLINN P. | Nov 2024
Nice house
Christy L. | Nov 2024
Very clean, great views, great pool. Already booked it for next year.
james v. | Nov 2024
Middle Keys, FL Frequently Asked Questions

Yes, 54 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. 146 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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