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, apartments, and more

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House rentals

View 32 House rentals
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Condo rentals

View 10 Condo rentals
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Apartments

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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

$229 avg / night
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$180 avg / night
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$181 avg / night
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$200 avg / night
Mariner's Retreat
4 Bedroom | 4 Bath | Sleeps 10

Mariner's Retreat - Key Largo, FL

$459 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

It’s near the pool and a short walk to the jetty. We had a great stay. You can walk to a seafood restaurant down the street or stroll the neighborhoods. We’re runners so we ran around the area each day. There are some nice tropical fish in the lagoon, and lots of iguanas around. We enjoyed Key Largo.
Rich Z. | Apr 2024
This was a wonderful property with amazing pools. I would stay here again in a heart beat.
Robin H. | Apr 2024
This condo was perfect for our stay and we look forward to coming again! Thank you
Chad L. | Apr 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   |   Islamorada   |   Tavernier   |   Key Largo   |   Florida
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