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.

Top Middle Keys, FL property types

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House rentals

View 58 House rentals
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Duplexes

View 23 Duplexes
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Condo rentals

View 17 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Palm Villa - Villa 5115
2 Bedroom | 2.5 Bath | Sleeps 6

Palm Villa - Villa 5115 - Duck Key, FL

$299 avg / night
(excludes fees and taxes)
4.28 (153)
Key Lime Villa
2 Bedroom | 2 Bath | Sleeps 6

Key Lime Villa - Duck Key, FL

$248 avg / night
(excludes fees and taxes)
4.74 (34)
Harbor Hideaway Villa 7066
4 Bedroom | 3 Bath | Sleeps 8

Harbor Hideaway Villa 7066 - Duck Key, FL

$378 avg / night
(excludes fees and taxes)
4.7 (20)
Blue Water Cottage Villa 5110
2 Bedroom | 1.5 Bath | Sleeps 6

Blue Water Cottage Villa 5110 - Duck Key, FL

$170 avg / night
(excludes fees and taxes)
4.75 (8)
Restful Retreat - Villa 5067
2 Bedroom | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$201 avg / night
(excludes fees and taxes)
4.48 (58)

View 108 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

I would have given this property 5 stars if it weren't for all the sensor spot lights. They are everywhere, if you like that prison yard feel, then this is the house for you! Aside from that it was a lovely well maintained property. One of the cleanest houses I've ever stayed in and Vacasa is very responsive and helpful.
Cynthia G. | Dec 2025
The house exceeded our expectations. The pictures do not do it justice. Spacious and very clean. Loved the location and the view. We took advantage of how close Havana Jacks was across the street for some snacks and drinks. Highly recommend. We usually stay on 8th street, but will more than likely return to this property.
Amanda D. | Dec 2025
Theis home is in great shape and the staff very nice and responsive. Property exactly as listing states. Great location as well. I would recommend.
Brandon B. | Dec 2025
Middle Keys, FL vacation rental FAQ

Yes, 38 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 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
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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   |   Coco Plum Beach - Marathon   |   Fat Deer Key - Key Colony Beach   |   Skipjack Resort & Marina - Marathon, FL   |   Marathon   |   Duck Key   |   Islamorada   |   Layton   |   Key Colony Beach   |   Conch Key   |   Long Key   |   Florida
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