Holiday Homes in Upper Matecumbe Key

"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "

"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "

"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."

"Great location of home. Easy to find. Quiet neighborhood. Plenty of parking spots available. Great views from both decks. Two clean bedrooms and 2 bathrooms. Plenty of stocked towels. Washer and dryer convenience with laundry soap available Very clean kitchen with soaps for dishes. Was missing pot holders and kitchen dish towel. Living area space and dining area a plus.Can’t wait to come back. "

"Quiet, clean, neighborhood feel."

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

"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "

"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"

"The unit was set up perfect for my family as well as my brother-in-law‘s for a family wedding in Key Largo. The pools were beautiful. The property was well maintained and we had a wonderful time. "

"The property was very clean. The kitchen was well equipped and the beds were very comfortable. "

"Beautiful condo in great location. Great beds!! "