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.

Explore Upper Keys, FL house rentals, condo rentals, apartments, and more

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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

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

$180 avg / night
(excludes fees and taxes)
4.09 (65)
Tavernier Escape #4408
2 Bed | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$252 avg / night
(excludes fees and taxes)
4.67 (42)
Oceanside Retreat - Ocean Pointe #4311
2 Bed | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

$268 avg / night
(excludes fees and taxes)
4.66 (114)
Coastal Living
3 Bed | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$420 avg / night
(excludes fees and taxes)
4.0 (5)
Kawama Yacht Club A4
2 Bed | 2 Bath | Sleeps 6

Kawama Yacht Club A4 - Key Largo, FL

$354 avg / night
(excludes fees and taxes)
4.35 (26)

View 24 more homes

Recent Upper Keys, FL vacation rental 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 Frequently Asked Questions

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 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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