Oceanfront vacation rentals on Upper Keys, FL

We found 11 vacation rentals waiting for you.

Wake up to the sand and surf

Claim your spot on the coast. With windows overlooking the waves, private balconies to watch the sunset, and amenities like pools and hot tubs, these Vacasa vacation homes on Upper Keys, FL will change the way you sea.

Top-rated oceanfront rentals on Upper Keys, FL

Our guests have spoken. Explore their favorite vacation homes on the shore. Take your pick from stunning ocean views to direct beach access, with waves practically at your doorstep.

Vitamin Sea - Ocean Pointe #3412
2 Bed | 2 Bath | Sleeps 6

Vitamin Sea - Ocean Pointe #3412 - Tavernier, FL

From $275
(excludes fees and taxes)
4.25 (64)
Oceanside Retreat - Ocean Pointe #4311
2 Bed | 2 Bath | Sleeps 6

Oceanside Retreat - Ocean Pointe #4311 - Tavernier, FL

From $303
(excludes fees and taxes)
4.64 (107)
Carysfort
4 Bed | 2 Bath | Sleeps 10

Carysfort - Key Largo, FL

From $442
(excludes fees and taxes)
Two J’s Paradise
2 Bed | 2 Bath | Sleeps 6

Two J’s Paradise - Key Largo, FL

From $387
(excludes fees and taxes)
4.78 (9)

Explore All Oceanfront Vacation Rentals

Recent guest reviews

Clean, comfortable and would stay again.
TERESA, J. | Jul 2025
The master bed footboard was falling apart, there where dirty wash cloths in the dresser in the guest room, and the smoke alarm randomly went off. Oh, and there was a roach in the master bedroom.
Carl D. | Jul 2025
4311 was great met our expectations two small balconies lots of wild life around. We had 5 of us and still plenty of room if you have a boat definitely bring it i didn't and really regret it they have boat slips and parking for the trailer
Ryan A. | Jul 2025
This was a fabulous place to go with friends for the weekend!!!
NANCY V. | Jun 2025
Best pricing

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Count on care—just a call, text, or email away.

Expert cleaning

Arrive to a spotless home with fresh linens.

FAQ

Yes, our oceanfront rentals offer direct beach access and are located just steps from the water.

Beach chairs, umbrellas, and other beach gear are often provided at many of our oceanfront vacation rentals. However, they are not a standard amenity across all oceanfront homes. We recommend reading the listing description thoroughly and looking at the home's list of amenities.

Many of our oceanfront vacation homes and condos include a private balcony or deck with stunning ocean views, along with water views from many of the rooms. Although that is not standard among all oceanfront rentals. We recommend looking at all the photos and taking a property’s 3D tour to make sure the property offers the amenities you’d like.

Some oceanfront rentals, especially those located on popular beaches, may include an outdoor shower or designated area to rinse off sand. This is not a standard feature across all rentals, but is more common in properties where guests participate in beach and water activities. We recommend reading the listing description thoroughly and looking at the home's list of amenities.

More ways to stay on Upper Keys, FL

Dog-friendly
Hot tub
Internet
Pool
Ocean view
Riverfront
Sound view
Soundfront

Nearby destinations

Gulf Coast
Florida's Atlantic Coast
South Florida
Southeast Florida
Florida Keys
Everglades National Park
Biscayne National Park
Islamorada
USA > Florida > Upper Keys, FL > Oceanfront

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