Upper Keys, FL Vacation Rentals

Compare 27 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 7 Condo rentals
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Apartments

View 1 Apartments

Explore more vacation rental amenities in Upper Keys, FL

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Fireplace | Washer/dryer | Bikes

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

$419 avg / night
(excludes fees and taxes)
4.09 (67)
Dolphin Paradise
5 Bed | 4.5 Bath | Sleeps 10

Dolphin Paradise - Key Largo, FL

$582 avg / night
(excludes fees and taxes)
Afternoon Delight
4 Bed | 4 Bath | Sleeps 10

Afternoon Delight - Key Largo, FL

$788 avg / night
(excludes fees and taxes)
5.0 (3)
Tavernier Escape #4408
2 Bed | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$471 avg / night
(excludes fees and taxes)
4.7 (50)
Coral Delight
2 Bed | 2.5 Bath | Sleeps 4

Coral Delight - Key Largo, FL

$560 avg / night
(excludes fees and taxes)

View 22 more homes

Recent Upper Keys, FL vacation rental reviews

I really enjoyed the entire resort. All of the amenities such as the pool and the hot tub were great! The condo itself was really amazing and very comfortable.
William T. | Mar 2026
Views!!, plenty of room, location
Rendall W. | Mar 2026
Great location
Diane C. | Mar 2026
Upper Keys, FL Frequently Asked Questions

Yes, 10 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. 27 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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