Middle Keys, FL Vacation Rentals

Compare 110 vacation rentals.
Home > 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.

Top Middle Keys, FL property types

housing_type_house.jpg

House rentals

View 56 House rentals
housing_type_duplex.jpg

Duplexes

View 23 Duplexes
housing_type_condo.jpg

Condo rentals

View 16 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Coastal Bliss Villa 7080
3 Bedroom | 3 Bath | Sleeps 8

Coastal Bliss Villa 7080 - Duck Key, FL

$304 avg / night
(excludes fees and taxes)
4.53 (19)
Blue Water Cottage Villa 5110
2 Bedroom | 1.5 Bath | Sleeps 6

Blue Water Cottage Villa 5110 - Duck Key, FL

$167 avg / night
(excludes fees and taxes)
4.62 (16)
The Endless Oasis
2 Bedroom | 2 Bath | Sleeps 6

The Endless Oasis - Marathon, FL

$263 avg / night
(excludes fees and taxes)
4.67 (12)
Restful Retreat - Villa 5067
2 Bedroom | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$188 avg / night
(excludes fees and taxes)
4.39 (64)
Key Lime Villa
2 Bedroom | 2 Bath | Sleeps 6

Key Lime Villa - Duck Key, FL

$259 avg / night
(excludes fees and taxes)
4.7 (37)

View 105 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

Loved the house itself! Super cute and clean. Had a couple of maintenance issues that were taken care of immediately. Only downfall is that building next door has lights on all night. There weren't any window coverings in the upstairs loft area so it was pretty bright for sleeping. Other than that, we loved the property!
Teri M. | Mar 2026
The house was beautiful, the kitchen had all the items we needed. The beds were all very comfortable and offered many options for bed size (king, queen). We enjoyed lots of time outside by the pools and utilized many items for recreation (chairs for sun and outdoor eating, kayaks, stand up paddle boards, beach chairs, pool floaties/toys, sonos speakers, ice maker in garage) The beds were very comfortable and the beach towels were great to use for the week. The Sonos sound system throughout the house and year were a great addition. The house is located within easy walking distance to the beach and about 1.5 miles to the nearest grocery/liquor store. We would stay at this house again. The house offer lots of room for privacy and room to relax but plenty of space to spend time together.
Patrick B. | Mar 2026
Your Place was beautiful , great pool and fishing dock. Wish the condo had beach chairs Highly recommend
KAREN L. | Mar 2026
Middle Keys, FL vacation rental FAQ

Yes, 37 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. 110 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
Vacasa Guest Value Prop Icon check-in
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   |   Long Key   |   Conch Key   |   Marathon   |   Key Colony Beach   |   Islamorada   |   Layton   |   Duck Key   |   Florida
Show more