Upper Keys, FL Vacation Rentals

Compare 42 vacation rentals with savings up to 30% off this summer.
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, duplexes, and more


House rentals

View 24 House rentals

Condo rentals

View 13 Condo rentals


View 2 Duplexes

Upper Keys, FL vacation rentals for every getaway

Dog-friendly Hot tub Internet
Kawama Yacht Club A4
2 Bedroom | 2 Bath | Sleeps 6

Kawama Yacht Club A4 - Key Largo, FL

$243 avg / night
Nauti Hideaway, Unit #2314
2 Bedroom | 2 Bath | Sleeps 6

Nauti Hideaway, Unit #2314 - Tavernier, FL

$238 avg / night
Tavernier Escape #4408
2 Bedroom | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$224 avg / night
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$211 avg / night
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$206 avg / night

View 37 more homes

Recent Upper Keys, FL vacation rental reviews

We enjoyed our condo very much. We felt right at home and wished we could stay longer. The ocean view from our condo was amazing.
JONATHAN T. | May 2023
The condo was well stocked with pots and pans, bathroom amenities soaps towels etc. Very clean great views. Even had laundry soap and dryer sheets something lots of condos over look. I will definitely stay there again. Mary
Mary M. | May 2023
Beautiful unit in a great location. Unit was clean and roomy and cool and beautifully decorated. There is one small bathroom upstairs for the two bedrooms. The downstairs bathroom, while convenient, was even smaller. Stairs were a bit steep and short for us.
Gene F. | May 2023
Upper Keys, FL vacation rental FAQ

Yes, 19 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. 42 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