Upper Keys, FL Vacation Rentals

Compare 35 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 26 House rentals
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Condo rentals

View 7 Condo rentals
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Apartments

View 1 Apartments

Explore more vacation rental amenities in Upper Keys, FL

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

Upper Keys, FL vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Ocean Pointe #2210
2 Bed | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$372 avg / night
4.07 (46)
Coastal Living
3 Bed | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$768 avg / night
1.0 (1)
Kawama Yacht Club A4
2 Bed | 2 Bath | Sleeps 6

Kawama Yacht Club A4 - Key Largo, FL

$643 avg / night
4.3 (20)
Oceanside Retreat: Ocean Pointe #4311
2 Bed | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$460 avg / night
4.67 (99)
Tavernier Escape #4408
2 Bed | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$522 avg / night
4.83 (30)

View 30 more homes

Recent Upper Keys, FL vacation rental reviews

The property and pool area were great. We really liked the location.
Christian F. | Jan 2025
Great house! Perfect for family and incredible views. Great area, quiet and nice people in neighborhood. Easy checkin and out. Will definitely be back.
Max H. | Jan 2025
True 4/ 4 bed bath. Very spacious nicely decorated wonderful downstairs outside area but TV doesn't get reception vacasa not very helpful won't use them again unless things change
Allen K. | Jan 2025
Upper Keys, FL Frequently Asked Questions

Yes, 12 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. 35 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

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