Middle Keys, FL Vacation Rentals

Compare 113 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, duplexes, condo rentals, and more

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House rentals

View 59 House rentals
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Duplexes

View 22 Duplexes
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Condo rentals

View 17 Condo rentals

Explore more vacation rental amenities in Middle Keys, FL

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

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Harbor Hideaway Villa 7066
4 Bed | 3 Bath | Sleeps 8

Harbor Hideaway Villa 7066 - Duck Key, FL

$547 avg / night
(excludes fees and taxes)
4.68 (19)
Blue Water Cottage Villa 5110
2 Bed | 1.5 Bath | Sleeps 6

Blue Water Cottage Villa 5110 - Duck Key, FL

$244 avg / night
(excludes fees and taxes)
4.75 (8)
Keys to Happiness
1 Bed | 2 Bath | Sleeps 4

Keys to Happiness - Marathon, FL

$192 avg / night
(excludes fees and taxes)
4.87 (15)
Restful Retreat - Villa 5067
2 Bed | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$290 avg / night
(excludes fees and taxes)
4.48 (58)
Palm Breeze - Villa 5030
2 Bed | 1.5 Bath | Sleeps 6

Palm Breeze - Villa 5030 - Duck Key, FL

$336 avg / night
(excludes fees and taxes)
3.99 (120)

View 108 more homes

Recent Middle Keys, FL vacation rental reviews

We loved the dock and ability to fish right there. Sunsets were beautiful, seen a variety of fish, stingrays, turtles, sharks, and even seen a dolphin one of the days. Pool made it nice for the kids without worry, down stairs bathroom made it convenient. Definitely would stay again.
Christina T. | Nov 2025
The house was cute and well equipped with children stuff which is a plus if you are traveling with kids. It is a little far from grocery stores but the location is beautiful!
Meghan M. | Nov 2025
Nice kitchen and big screen tv!
Kim S. | Nov 2025
Middle Keys, FL Frequently Asked Questions

Yes, 39 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. 112 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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