Upper Keys, FL Vacation Rentals

Compare 37 vacation rentals.
An error was detected and reported for this component.
USA > Florida > Upper Keys, FL

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

housing_type_house.jpg

House rentals

View 28 House rentals
housing_type_condo.jpg

Condo rentals

View 7 Condo rentals
housing_type_apartment.jpg

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

$299 avg / night
4.19 (54)
Vitamin Sea - Ocean Pointe #3412
2 Bed | 2 Bath | Sleeps 6

Vitamin Sea - Ocean Pointe #3412 - Tavernier, FL

$337 avg / night
4.23 (62)
Tavernier Escape #4408
2 Bed | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$406 avg / night
4.81 (32)
Oceanside Retreat - Ocean Pointe #4311
2 Bed | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

$363 avg / night
4.64 (103)
Whispering Wake
3 Bed | 3 Bath | Sleeps 10

Whispering Wake - Key Largo, FL

$328 avg / night

View 32 more homes

Recent Upper Keys, FL vacation rental reviews

Very nice home, except for the downstairs bathroom which is much too small. Gorgeous locale close to fabulous seafood restaurants that is close enough to Key West to make it a gem of a location, especially given all of the things you can do in Key Largo itself that will make any trip to the Keys worthwhile. Very clean and very comfortable. Would definitely come here again, despite the small downstairs bathroom.
John I P. | Apr 2025
Manatees and fish in the canal. Great restaurants and bars nearby. Plenty of great kayaking spots. Beautiful views and sunsets. Perfect place and a great vacation.
Lee S. | Apr 2025
Great location and a lot of room and balconies! Would stay there again!
angela m. | Mar 2025
Upper Keys, FL Frequently Asked Questions

Yes, 12 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. 37 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

People also search for

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Everglades National Park   |   Biscayne National Park   |   Islamorada   |   Key Largo   |   Tavernier   |   Florida
Show more  
Su
Mo
Tu
We
Th
Fr
Sa
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3