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

Popular amenities for Upper Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Coastal Living
3 Bedroom | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$528 avg / night
1.0 (1)
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$258 avg / night
4.07 (46)
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$322 avg / night
4.67 (99)
Kawama Yacht Club A4
2 Bedroom | 2 Bath | Sleeps 6

Kawama Yacht Club A4 - Key Largo, FL

$447 avg / night
4.3 (20)
Tavernier Escape #4408
2 Bedroom | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$363 avg / night
4.86 (29)

View 30 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

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
Convenient to everything
Ray H. | Jan 2025
Upper Keys, FL vacation rental FAQ

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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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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