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
TA42 The Tree Lane Fish Camp
3 Bed | 2 Bath | Sleeps 6

TA42 The Tree Lane Fish Camp - Tavernier, FL

$481 avg / night
(excludes fees and taxes)
Islander Retreat
3 Bed | 4 Bath | Sleeps 8

Islander Retreat - Key Largo, FL

$375 avg / night
(excludes fees and taxes)
4.25 (8)
Molliner Vacation Retreat
2 Bed | 2 Bath | Sleeps 6

Molliner Vacation Retreat - Tavernier, FL

$459 avg / night
(excludes fees and taxes)
4.0 (6)
Tropical Bliss
3 Bed | 2 Bath | Sleeps 8

Tropical Bliss - Key Largo, FL

$583 avg / night
(excludes fees and taxes)
Whispering Wake
3 Bed | 3 Bath | Sleeps 10

Whispering Wake - Key Largo, FL

$507 avg / night
(excludes fees and taxes)
5.0 (1)

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
Beautiful home and property. Perfect for a family with children and close to everything!
Monica G. | Mar 2026
Upper Keys, FL Frequently Asked Questions

Yes, 8 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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