Middle Keys, FL Vacation Rentals

Compare 126 vacation rentals.
1 Guest
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

housing_type_house.jpg

House rentals

View 63 House rentals
housing_type_duplex.jpg

Duplexes

View 30 Duplexes
housing_type_condo.jpg

Condo rentals

View 19 Condo rentals

Popular amenities for Middle Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Sombrero Siesta
1 Bedroom | 1 Bath | Sleeps 4

Sombrero Siesta - Marathon, FL

$269 avg / night
(excludes fees and taxes)
4.32 (41)
Restful Retreat - Villa 5067
2 Bedroom | 1.5 Bath | Sleeps 6

Restful Retreat - Villa 5067 - Duck Key, FL

$325 avg / night
(excludes fees and taxes)
4.44 (52)
Coastal Bliss Villa 7080
3 Bedroom | 3 Bath | Sleeps 8

Coastal Bliss Villa 7080 - Duck Key, FL

$522 avg / night
(excludes fees and taxes)
5.0 (5)
Harbor Hideaway Villa 7066
4 Bedroom | 3 Bath | Sleeps 8

Harbor Hideaway Villa 7066 - Duck Key, FL

$482 avg / night
(excludes fees and taxes)
4.71 (14)
Bayfront Sunset Oasis
4 Bedroom | 2.5 Bath | Sleeps 10

Bayfront Sunset Oasis - Marathon, FL

$983 avg / night
(excludes fees and taxes)
4.85 (84)

View 121 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

We loved the condo. It was perfect for just the two of us or maybe two couples or small Family. The bedrooms are extremely small but the two outdoor porches made up for it, especially the private pool! We had other family members staying g on condos nearby making a perfect place for a group to meet up!
Sarah V. | Jun 2025
We had a fantastic stay; the home exceeded our expectations. The property was clean, decorated well, and equipped with everything we could need. The location was great and allowed for easy access by boat to Vaca Cut.
Ryan B. | Jun 2025
The was was very clean, had great amenities and the staff was quick to respond to our inquiries
H Francisco G. | Jun 2025
Middle Keys, FL vacation rental FAQ

Yes, 43 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. 125 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   |   Lower Keys, FL   |   Coco Plum Beach - Marathon   |   Fat Deer Key - Key Colony Beach   |   Skipjack Resort & Marina - Marathon, FL   |   Islamorada   |   Marathon   |   Duck Key   |   Layton   |   Key Colony Beach   |   Long Key   |   Conch Key   |   Florida
Show more  
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5