Search Condos 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

In two weeks

In two months

In three months

In four months

Featured Condo Rentals in Upper Matecumbe Key

Our top choices for Upper Matecumbe Key condo rentals

On the beach, sun-loungers, beach towels

"Great vacation spot , only thing missing is a good saltwater beach."

"Cute apartment perfectly located in the complex with proximity to the pool and beach areas. Comfortable for 4 adults "

"Great unit, nicely renovated and a good weekend! "

"This was the perfect place to stay!Nice & clean!Close to activities and restaurants!The owner was very easy to communicate with!We will definitely stay here again next time we are in the Keys!"

"The property was very clean and comfortable. The pool was beautiful. The condo fit all of our needs and we were glad yo have the opportunity to stay. We would love to come back!"

"Great place to stay friendly staff awesome pool! Condo was so clean and very comfortable felt like home! "

"Great place to spend some time in the Keys. We made a quick fishing trip from New England. Check in was easy, host is extremely responsive. "

"We liked everything about the property. This is a quite end unit and was nicely finished. Would definitely highly recommend staying here."

"Everything was exactly like the listing! Would definitely stay there again"

"Great location. Very clean and beautiful views"

"Beautiful home, clean and had all we needed, no problems at all with one of the swimmjng pools right outside the condo which made it very convenient. Only thing that would have made it over the top was to have a sandy beach with swimming area on site, otherwise, it was great!"

"Great place to take your family and enjoy doing nothing but relaxing by the pool or on the beach. "

Beach nearby, sun-loungers, beach towels

"This was a wonderful base of operations for our family vacation in the Keys!"

"The property is naturally beautiful, safe, and secluded! The staff, especially Alex and Alex, are amazing! Thank you, Alex, for making our stay--for the 4th time--a great one! "

includes taxes & fees

5 Oct - 6 Oct

"Very clean and nice"

"Very nice place for two couples! "

"Very clean and spacious condo. Pool area very quiet and relaxing - no crowds. Enjoyed the pickle ball courts. Quick drive to restaurants."

"Great getaway"

"Wonderful stay at a clean and convenient location!The host was very responsive and provided both directions regarding the stay and recommendations for local activities. The beach and marina are an easy walk from the condo and the pool is right across the parking lot."