Upper Keys, FL Vacation Rentals

Compare 27 vacation rentals.
Home > USA > Florida > Upper Keys, FL

Make Upper Keys, FL your next getaway

Explore our vacation rentals on Upper 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 Upper Keys, FL house rentals, condo rentals, apartments, and more

housing_type_house.jpg

House rentals

View 17 House rentals
housing_type_condo.jpg

Condo rentals

View 8 Condo rentals
housing_type_apartment.jpg

Apartments

View 1 Apartments

Upper Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Tavernier Escape #4408
2 Bed | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$265 avg / night
(excludes fees and taxes)
4.66 (41)
Ocean Pointe #2210
2 Bed | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$185 avg / night
(excludes fees and taxes)
4.14 (64)
Oceanside Retreat - Ocean Pointe #4311
2 Bed | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

$282 avg / night
(excludes fees and taxes)
4.65 (112)
Coastal Living
3 Bed | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$431 avg / night
(excludes fees and taxes)
4.0 (5)
Molliner Vacation Retreat
2 Bed | 2 Bath | Sleeps 6

Molliner Vacation Retreat - Tavernier, FL

$294 avg / night
(excludes fees and taxes)
5.0 (1)

View 22 more homes

Recent Upper Keys, FL vacation rental reviews

We absolutely loved our stay. The condo was very clean, comfortable and nicely updated. The large pool area offered plenty of chairs, food, drinks and music. We didn't hang out on the beach much but walked down to the marina/gazebo a few times for sunrise and sunset. We saw a small bonnet shark, a sting ray and a small fish in the water. There were also 2 ospreys in the osprey nest and plenty of other birds. The neighborhood cats and raccoons came out at night but they would disappear in the mangroves when anyone came near. The entire establishment is very well cared for and it shows. We would definitely return. Check in and check out was super easy. They even provided beach towels! A few things for the owner: a small chair would be a nice addition to living room. The couch was not big enough for the 4 of us to watch a movie at night so a small accent chair in front of the bar would have been nice. Also, one full length mirror would have been lovely for us girls:) Also, the bedspreads were made of a very thin polyester and uncomfortable. Cotton quits and sheets would be a nice touch. The bathroom leading to the twin bedroom did not have a lock on the door from inside the bedroom. It needs one for sure. Also, the master bedroom did not lock. All bedroom and bathroom doors could use a good oiling. They all squeaked loudly when opened/closed during middle of the night potty trips. As for amenities, we enjoyed all! However, a covered grill area would be nice if it's sprinkling or for shade. But the grills don't work, it took about 90 minutes just to grill hot dogs, which was quite unexpected. Gas grills would be much more ideal. Vacasa provided a starter kit but no starter laundry pods so bring your own. Also, my fault for not bringing a little beach bag. Some rental companies include it with the starter kit but this company does not. All in all, great experience at this condo and with Vacasa. 5 stars
Wende P. | Dec 2025
This was a well stocked apartment with a lot of thought put into the contents. If you plan to cook know that you will need to purchase everything down to salt and pepper. Very clean!
Mamta B. | Nov 2025
The views are amazing...both sunrise and sunset. The bed (master suite) was super comfortable...the fact that laundry is available right in the unit is awesome
Darci C. | Nov 2025
Upper Keys, FL Frequently Asked Questions

Yes, 8 of our Upper 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. 27 of our Upper 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 Upper 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 Upper 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 Upper 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