Search Villas in Upper Matecumbe Key

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured Villas in Upper Matecumbe Key

Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

"Absolutely outstanding resort. Legitimate 5 star property. "

includes taxes & fees

6 Aug - 7 Aug

Enjoy cooking in this well-equipped kitchen with stainless steel appliances and ample natural light.

"This was a great place to stay away from the business but close enough to Marathon to go to dinner or activities. The condo was cozy and had a great sunset view. Will definitely look at this place again if we return to the Keys."

Relax in this inviting living space with a sofa, chair, and TV, perfect for unwinding and taking in the view.

"Very clean. "

includes taxes & fees

4 Aug - 5 Aug

Boats docked in a serene marina surrounded by lush greenery and palm trees.

"Great location Vivian was very responsive to any questions we had"

Relax by the pool or enjoy a drink at the adjacent bar amidst lush palm trees and serene surroundings.

"Enjoy the stay in good location "

Escape to a serene beachside haven surrounded by tall palm trees and lush greenery.

"Perfect place to relax "

Relax by the serene pool surrounded by lush tropical plants and palm trees.

"We enjoyed our stay!"

Enjoy a serene view from the comfort of your room, which opens onto a patio with outdoor seating and lush surroundings.

"We had a wonderful expérience in Duck Key.Thank you Ana for your kind hospitality!See you next time !"

Relax in Adirondack chairs on the beach, overlooking the ocean with sailboats on the water.

"We enjoy the property and great Key Largo location. Owner was very quick to respond to questions. Some repairs are needed that he is aware of and he said they would be fixed soon. "

Escape to a serene oasis surrounded by lush greenery and a tranquil body of water.

"The property has potential but needs A lot of maintenance and upgrades. Also wasn’t very clean. In addition since they do not participate of hawks cay resort program you can’t enjoy the area. I stayed in this area and other owners are part of the program so you can enjoy the amenities around "

Relax by the serene pool surrounded by palm trees and lounge chairs.

"We stayed for 4 nights, 2 adults and 2 kids. It was a pleasant stay. "

Relax by the ocean with a serene pool and lounge area, offering a tranquil escape.

"Great house. Nice amenities- peaceful and secluded. However no beach access from house. Nearest beach is Sombrero beach which is very nice."

Situated on a rocky shoreline, this coastal property offers access to the sea via a wooden dock.

"We enjoyed our stay."

Enjoy a serene view of the water from this deck with a round table and four chairs.

"Great location on the water with beautiful sunset views. Plenty of room for our group. "

includes taxes & fees

26 Aug - 27 Aug

Enjoy a tranquil retreat with a pool and serene waterfront views.

"Great location, incredible view just as advertised. Definitely would stay there again."

includes taxes & fees

4 Aug - 5 Aug

Relax on the spacious balcony with a sofa set and individual chairs, overlooking a serene landscape.

"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."

Relax by the serene pool surrounded by lush greenery and a thatched-roof gazebo.

"This was a beautiful spot for 3 couples to relax and enjoy this beautiful setting. The outside space was perfect with tables, firepit & grills. The house was stocked well enough to be able to prepare some meals. I would definitely return again."

Enjoy a serene ocean view from the resort's pool, surrounded by lush greenery and palm trees.

"Anglers Way was a meticulously clean property centrally located on Islamorada. The hosts were extremely responsive to our inquiries prior to and during our stay in their home. The property was well equipped and provided for all our needs. They undoubtedly deserve our 5 star review and would recommend this property for those seeking a restful vacation. "