Upper Keys, FL Vacation Rentals

Compare 37 vacation rentals.
1 Guest
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

Popular amenities for Upper Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$245 avg / night
(excludes fees and taxes)
4.18 (57)
Tavernier Escape #4408
2 Bedroom | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$313 avg / night
(excludes fees and taxes)
4.79 (34)
Vitamin Sea - Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea - Ocean Pointe #3412 - Tavernier, FL

$260 avg / night
(excludes fees and taxes)
4.24 (63)
Lookout at Lorelane
3 Bedroom | 2 Bath | Sleeps 9

Lookout at Lorelane - Key Largo, FL

$217 avg / night
(excludes fees and taxes)
Oceanside Retreat - Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

$293 avg / night
(excludes fees and taxes)
4.64 (106)

View 32 more homes

Browse more vacation rental amenities in Upper Keys, FL

Pool | Ocean view | Oceanfront | Riverfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator

Recent Upper Keys, FL guest reviews

This was a perfect getaway. Very clean, courteous staff. Easy to get too, private beach and dock.
Mylina Y. | Jun 2025
We had such an amazing time staying here! From the second we walked in, the place felt so welcoming and cozy — super clean, nicely decorated, and stocked with everything we needed. You can really tell the host puts a lot of thought into the little details. The location couldn’t be better. It’s close to great restaurants, fun local spots, and just a short drive to some of the best snorkeling and kayaking we’ve ever done. One morning we even spotted manatees right near the dock — total highlight of the trip! We spent our evenings relaxing on the patio, and it honestly felt like our own little slice of paradise. The whole stay was peaceful, easy, and just what we needed to unwind. Highly recommend this place if you’re visiting Key Largo, we’re already talking about coming back!
Julio S. | May 2025
Beautiful views, Clean and comfortable.
Shawn P. | May 2025
Upper Keys, FL vacation rental FAQ

Yes, 14 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 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   |   Key Largo   |   Islamorada   |   Tavernier   |   Florida
Show more  
Su
Mo
Tu
We
Th
Fr
Sa
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
4
5