Upper Keys, FL Vacation Rentals

Compare 34 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

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House rentals

View 25 House rentals
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Condo rentals

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Apartments

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Popular amenities for Upper Keys, FL vacation rentals

Popular
Dog-friendly Hot tub Internet
Tavernier Escape #4408
2 Bedroom | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$303 avg / night
4.81 (32)
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$219 avg / night
4.17 (53)
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$263 avg / night
4.65 (102)
Coastal Living
3 Bedroom | 3 Bath | Sleeps 8

Coastal Living - Key Largo, FL

$419 avg / night
3.33 (3)
Kawama Yacht Club A4
2 Bedroom | 2 Bath | Sleeps 6

Kawama Yacht Club A4 - Key Largo, FL

$329 avg / night
4.26 (23)

View 29 more homes

Recent Upper Keys, FL guest reviews

This home was perfect for a get away to Key Largo. The location was ideal with easy access to both a beach area and a pool! We were able to communicate directly with the owner if we had any problems. Felt very safe and would definitely stay here again!!!
Caroline K. | Mar 2025
Overall this was a great property with amazing views. The balconies are so ridiculously small that they almost aren't worth having. There was hardly any room for two small chairs and a tiny table, and even then one person had to go out and sit down before the other person could go out on the balcony. The views were fantastic, so that sort of made up for the tiny balconies. The condo was clean and seemingly well maintained other than a few spots that need some paint touchup. However, we kept finding German cockroaches on the kitchen counter near the sink, at least 7 over the course of 2 days. We checked our food items and did not find roaches in the items we brought in, so they are living somewhere in the kitchen. The kitchen has a decent supply of plates, bowls, glasses, utensils, and some very basic pots and pans. Nothing other than coffee and sugar, so if you're planning to do any cooking, you'll need to bring your own spices, herbs, seasonings, and condiments. There were plenty of bath towels and beach towels, along with soap and shampoo. The beach umbrella was great to have. The private beach with lounge chairs was nice.
Randy S. | Mar 2025
The location in Tavenier was awesome. Lots to do between Key Largo and Islamorada. Communication with Vacasa was also excellent!
Melissa D. | Mar 2025
Upper Keys, FL vacation rental FAQ

Yes, 11 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. 34 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
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Seamless check-in
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Professional cleaning
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