Upper Keys, FL Vacation Rentals

Compare 29 vacation rentals.
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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.

Top Upper Keys, FL property types

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House rentals

View 18 House rentals
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Condo rentals

View 9 Condo rentals
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Apartments

View 1 Apartments

Popular amenities for Upper Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Tavernier Escape #4408
2 Bedroom | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$184 avg / night
(excludes fees and taxes)
4.67 (42)
Kawama Yacht Club A4
2 Bedroom | 2 Bath | Sleeps 6

Kawama Yacht Club A4 - Key Largo, FL

$259 avg / night
(excludes fees and taxes)
4.35 (26)
Oceanside Retreat - Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

$196 avg / night
(excludes fees and taxes)
4.66 (114)
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$132 avg / night
(excludes fees and taxes)
4.09 (65)
Coastal Living
3 Bedroom | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$307 avg / night
(excludes fees and taxes)
4.0 (5)

View 24 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

The home was very spacious in a great location and was very well equipped with everything you needed. The neighborhood’s private beach was beautiful and the neighbors friendly. We had a great month in Key Largo.
Betty A. | Jan 2026
Great location, beautiful view, great pool, restaurant on site, great condo rooms and baths. Highly recommend.
LARRY S. | Jan 2026
The room was clean, great seating area, plenty of towels, had a washer and dryer. Loved the room and the area!
Stacy V. | Jan 2026
Upper Keys, FL vacation rental FAQ

Yes, 9 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. 29 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Upper Keys, FL, log in to Trip Manager to explore the 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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