Middle Keys, FL Vacation Rentals

Compare 96 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.

Explore Middle Keys, FL house rentals, condo rentals, townhouses, and more

housing_type_house.jpg

House rentals

View 64 House rentals
housing_type_condo.jpg

Condo rentals

View 13 Condo rentals
housing_type_townhouse.jpg

Townhouses

View 8 Townhouses

Middle Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
LK01a - The Zane Grey
2 Bed | 1 Bath | Sleeps 6

LK01a - The Zane Grey - Long Key, FL

$802 avg / night
(excludes fees and taxes)
4.73 (73)
KC100 - Breezy Keys
4 Bed | 2 Bath | Sleeps 8

KC100 - Breezy Keys - Key Colony Beach, FL

$620 avg / night
(excludes fees and taxes)
5.0 (4)
KC01 - Captain's Haven
3 Bed | 3 Bath | Sleeps 8

KC01 - Captain's Haven - Key Colony Beach, FL

$709 avg / night
(excludes fees and taxes)
4.77 (52)
MA149 - Ouellette Oasis
3 Bed | 3 Bath | Sleeps 8

MA149 - Ouellette Oasis - Marathon, FL

$606 avg / night
(excludes fees and taxes)
4.95 (20)
MA209 - Overseas Beauty
1 Bed | 2 Bath | Sleeps 4

MA209 - Overseas Beauty - Marathon, FL

$238 avg / night
(excludes fees and taxes)
4.75 (8)

View 91 more homes

Recent Middle Keys, FL vacation rental reviews

We had a great stay with our family. The house was very clean and the amenities provided made sure we had everything that we needed. It was great to have beach chairs and beach toys for the kids.
Jennifer D. | Jul 2026
Our family had the best time during our stay at this home! We stay in Marathon every year with our dogs, and this has been the best house yet. The kids loved the pool and the outdoor area is really nice for families and hanging out. The boat dock is a little tricky, the tide does vary greatly, meaning it comes up quite a bit during high tide so secure the boat properly so it does not come up under the dock during high tide. Also the canal is very shallow during low tide, just an FYI. The boat ramp is close by which is also nice. You feel at your own oasis here, there are plenty of greenery and the road isn't busy. Publix is on the same road, huge plus with a family! The kitchen has so many utensils and just so many little details that make your stay so much more enjoyable. Chelsea was very responsive and helpful! This place is a true gem. It is hard to find places like this that check many boxes in the keys!
Michelle . | Jul 2026
Our family had the best time during our stay at this home! We stay in Marathon every year with our dogs, and this has been the best house yet. The kids loved the pool and the outdoor area is really nice for families and hanging out. The boat dock is a little tricky, the tide does vary greatly, meaning it comes up quite a bit during high tide so secure the boat properly so it does not come up under the dock during high tide. Also the canal is very shallow during low tide, just an FYI. The boat ramp is close by which is also nice. You feel at your own oasis here, there are plenty of greenery and the road isn't busy. Publix is on the same road, huge plus with a family! The kitchen has so many utensils and just so many little details that make your stay so much more enjoyable. Chelsea was very responsive and helpful! This place is a true gem. It is hard to find places like this that check many boxes in the keys!
Michelle . | Jul 2026
Middle Keys, FL Frequently Asked Questions

Yes, 31 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. 96 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