Upper Keys, FL Vacation Rentals

Compare 44 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

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House rentals

View 32 House rentals
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Condo rentals

View 9 Condo rentals
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Townhouses

View 2 Townhouses

Popular amenities for Upper Keys, FL vacation rentals

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

Nauti Hideaway, Unit #2314 - Tavernier, FL

$248 avg / night
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$193 avg / night
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$210 avg / night
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$230 avg / night
Mariner's Retreat
4 Bedroom | 4 Bath | Sleeps 10

Mariner's Retreat - Key Largo, FL

$463 avg / night

View 39 more homes

Browse more vacation rental amenities in Upper Keys, FL

Pool | Ocean view | Oceanfront | Riverfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator

Recent Upper Keys, FL guest reviews

Very nice house with great view Enjoyed our vacation.
michelle s. | May 2024
The view from the unit.
Frank M. | May 2024
Everything was close by. Foo, gas, beach......
Brenda E. | 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. 44 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

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Everglades National Park   |   Biscayne National Park   |   Key Largo   |   Islamorada   |   Tavernier   |   Florida
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