Holiday Homes in Upper Matecumbe Key

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Featured Holiday Homes in Upper Matecumbe Key

"Everything just great except need better vaccum"

Beach nearby, sun-loungers, beach towels

"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "

includes taxes & fees

3 Sept - 4 Sept

"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"

"Clean , beautiful location and pools . "

"We used this as accommodation to explore the keys for 6days and it did not disappoint. Very accurate description of the house. Nice, clean and tidy. Thank you"

"Best sunrise site."

includes taxes & fees

25 Aug - 26 Aug

"Great location. Beautiful, comfortable accommodations. Would absolutely return. "

"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. "

includes taxes & fees

13 Aug - 14 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

21 Aug - 22 Aug

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

"This property was amazing basically brand new definitely recommend "

"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. "

"beautiful and quite neighborhood. "

"Quiet, clean, neighborhood feel."

"The porperty had everything we needed for a great family spring break. The kids especially enjoyed trips to the jetty on the golf cart!"

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

"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!"

"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! "