Upper Keys, FL Vacation Rentals

Compare 36 vacation rentals.
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 27 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
Ocean Pointe #2210
2 Bedroom | 2 Bath | Sleeps 4

Ocean Pointe #2210 - Tavernier, FL

$200 avg / night
4.07 (46)
Vitamin Sea: Ocean Pointe #3412
2 Bedroom | 2 Bath | Sleeps 6

Vitamin Sea: Ocean Pointe #3412 - Tavernier, FL

$238 avg / night
4.25 (61)
Oceanside Retreat: Ocean Pointe #4311
2 Bedroom | 2 Bath | Sleeps 6

Oceanside Retreat: Ocean Pointe #4311 - Tavernier, FL

$259 avg / night
4.65 (92)
Tavernier Escape #4408
2 Bedroom | 2 Bath | Sleeps 6

Tavernier Escape #4408 - Tavernier, FL

$298 avg / night
4.86 (28)
Two J’s Paradise
2 Bedroom | 2 Bath | Sleeps 6

Two J’s Paradise - Key Largo, FL

$406 avg / night
4.71 (7)

View 31 more homes

Recent Upper Keys, FL guest reviews

Gorgeous view never even closed the curtains at night to enjoy the panoramic ocean views listening to the ocean all the wildlife offspring pelicans flying by sunset sunrise room was decorated beautifully, super clean and comfortable beds, ice cold air conditioner all the amentaties you have at home great communication via the app
Anthony V. | Nov 2024
Every morning watching the spectacular sunrises with my coffee on the deck was magical. Being right on the ocean and the wrap around deck was our spot until dinner. That is except when I would escape to the swing on the bottom level. There are sliding glass windows that let the sun in from everywhere you look in the kitchen and the living room. You also have another in the master bathroom. Being at the end of the street with woods and a canal, it was very private and calming. If you go down and dip your feet in the ocean, there is an outside shower to remove the salt water. The owner had a washer and dryer at our disposal, and a grill, but we love the local restaurants. We have been going here for many years and would not stay anywhere else. The owner is so pleasant and helpful. I wish I could share all my photos. Here is one of my favorites.
Kathy R. | Nov 2024
This is our third stay at Ocean Pointe and we love it. We've had NASCAR tickets for Homestead since 2015 and had always stayed in Miami. We decided to try something different and love this location. Traveling to the track with Homestead is quicker than coming from Miami. And we love the Keys, Tavernier is a great place to stay. It's quick trip down the highway to Key West. The condo has everything we need. That ocean view is fantastic. We had coffee on the balcony every morning. Amenities are great. The pool area is nice with loungers, tables and umbrellas. Everything, the pool, spa, and pool deck and are clean. We're back in Florida again in March, and we'd stay here again, but unfortunately those dates we need are booked. We'll try again in 2026.
Margaret A. | Nov 2024
Upper Keys, FL vacation rental FAQ

Yes, 13 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. 36 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
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Professional cleaning