Upper Keys, FL Vacation Rentals

Compare 43 vacation rentals.
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, townhouses, and more


House rentals

View 31 House rentals

Condo rentals

View 9 Condo rentals


View 2 Townhouses

Popular amenities for Upper Keys, FL vacation rentals

Dog-friendly Hot tub Internet
Nauti Hideaway, Unit #2314
2 Bedroom | 2 Bath | Sleeps 6

Nauti Hideaway, Unit #2314 - Tavernier, FL

$279 avg / night
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$221 avg / night
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$243 avg / night
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$263 avg / night
Mariner's Retreat
4 Bedroom | 4 Bath | Sleeps 10

Mariner's Retreat - Key Largo, FL

$520 avg / night

View 38 more homes

Recent Upper Keys, FL guest reviews

Loved the pool! The house was nice after maintenance fixed our issues more than 24 hours after notification.
Beth Ann T. | May 2024
Clean, roomy house with great views in a great location.
Patrick D. | May 2024
Loved the view up the canal and the hot tub.
Gary G. | May 2024
Upper Keys, FL vacation rental FAQ

Yes, 14 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. 43 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