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.

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

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House rentals

View 17 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
Tavernier Escape #4408
2 Bed | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$267 avg / night
(excludes fees and taxes)
4.65 (40)
Vitamin Sea - Ocean Pointe #3412
2 Bed | 2 Bath | Sleeps 6

Vitamin Sea - Ocean Pointe #3412 - Tavernier, FL

$190 avg / night
(excludes fees and taxes)
4.26 (66)
Molliner Vacation Retreat
2 Bed | 2 Bath | Sleeps 6

Molliner Vacation Retreat - Tavernier, FL

$299 avg / night
(excludes fees and taxes)
5.0 (1)
Oceanside Retreat - Ocean Pointe #4311
2 Bed | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

$285 avg / night
(excludes fees and taxes)
4.65 (112)
Coastal Living
3 Bed | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$437 avg / night
(excludes fees and taxes)
4.0 (5)

View 23 more homes

Recent Upper Keys, FL vacation rental reviews

This property is top notch. Totally worth the price. The beach is small but it’s a nice little beach. There’s no negatives to this property. It made our vacation.
RICHARD L. | Nov 2025
This was a well stocked apartment with a lot of thought put into the contents. If you plan to cook know that you will need to purchase everything down to salt and pepper. Very clean!
Mamta B. | Nov 2025
The views are amazing...both sunrise and sunset. The bed (master suite) was super comfortable...the fact that laundry is available right in the unit is awesome
Darci C. | Nov 2025
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. 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 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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