Upper Keys, FL Vacation Rentals

Compare 28 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 8 Condo rentals
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Apartments

View 1 Apartments

Popular amenities for Upper Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Executive Bay Club Condo M-1
2 Bedroom | 2 Bath | Sleeps 6

Executive Bay Club Condo M-1 - Islamorada, FL

$159 avg / night
(excludes fees and taxes)
3.91 (11)
Coral Delight
2 Bedroom | 2.5 Bath | Sleeps 4

Coral Delight - Key Largo, FL

$344 avg / night
(excludes fees and taxes)
The Beach House
2 Bedroom | 1 Bath | Sleeps 6

The Beach House - Key Largo, FL

$283 avg / night
(excludes fees and taxes)
Tarpon Cove
2 Bedroom | 2 Bath | Sleeps 4

Tarpon Cove - Tavernier, FL

$328 avg / night
(excludes fees and taxes)
4.67 (12)
Islamorada Haven
2 Bedroom | 1 Bath | Sleeps 6

Islamorada Haven - Tavernier, FL

$223 avg / night
(excludes fees and taxes)
5.0 (2)

View 23 more homes

Browse more vacation rental amenities in Upper Keys, FL

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

Recent Upper Keys, FL guest 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 vacation rental FAQ

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. 28 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   |   Tavernier   |   Islamorada   |   Key Largo   |   Florida
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