Search Holiday Homes in Upper Matecumbe Key

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Browse Select Upper Matecumbe Key Holiday Homes

"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"

"loved it!!"

includes taxes & fees

18 Aug - 19 Aug

"Everything just great except need better vaccum"

"The house is great, tidy little spot to start all your Keys adventures from!"

includes taxes & fees

18 Aug - 19 Aug

"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "

"We had a Wonderful time! There was plenty of space for our family of five. We had a few minor issues with ants, but it did not impact our comfortable stay. We loved the pool and Pickleball court! Would highly recommend. "

"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."

"Such a great, gated location with access to a variety of amenities. "

"Great trip. Very comfortable for family of 5. Cabana club lovely and great recommendations!"

"Clean , beautiful location and pools . "

"Very clean, good location, easy access to boat ramp/dock"

includes taxes & fees

18 Aug - 19 Aug

"You would be very hard presses to find a better Key Largo location. Especially for family, boating and fishing!"

includes taxes & fees

18 Aug - 19 Aug

"My wife and I stayed here for our honeymoon , and we were absolutely thrilled with everything. We loved that the house had a bunch of mini splits to keep it nice and chilly. We also loved that the house was very clean and well kept. The tiki hut on the water with the tv and great lighting at night makes a perfect place to relax at the end of a fun filled day. All around this was a fantastic place to stay!"

includes taxes & fees

8 Sept - 9 Sept

"It was perfect for my family- had everything we needed. Nice area to avoid crowds, but fast to drive to stores/restaurants as needed. "

"Beautiful place in the keys, and felt larger than the photos showed. Owner is very communicative! "

"We had a great stay! We loved having kayaks, snorkels, a lagoon and the ocean and everything nearby. We loved feeding the fish on the property. The kitchen is well stocked with everything we needed for making meals. Nice restaurants nearby! Thanks for meeting us, Norman - that was very helpful!!"

"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."

"Excellent location off the main drag with quiet stay and perfect place to have as a base of operation for sightseeing and fishing."

"The upper deck has a great sunset view. Great area for walks. Very quiet and peaceful neighborhood. Would definitely stay again next time in the Keys"