Search Holiday Rentals in Upper Matecumbe Key

"Staff was great, pool area was beautiful. Great Food and drink options. Very relaxing, did not need to leave the resort. Shout out to Matt the bartender who was amazing!"

"Super "

"My son and his new wife had an amazing time on their honeymoon! They said everything was top notch and have gone on & on about what an amazing time they had! ⭐️⭐️⭐️⭐️⭐️"

"Staff was extremely accommodating, Property is stunning with numerous activities. "

"Excelent"

"used tge dock very easy "

"The rooms are showing their age but all new remodeling starts soon. Staff very professional and met all our needs. Breakfast was great. Extremely convenient for our trip. We recommend and would stay there again."

"We had a room with an ocean view and it was great. There was a beautiful double rainbow over the water one of the days we were there."

"Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect when starting with Krystal's French toast. Her smile is infectious. She and the breakfast gang aim to please with their attention to detail. The private beach is lovely with shade and sun options. No talking or music. It was the perfect spot to watch the boats at the sand bar or to take a nap. Walk through the adjacent parking lot to four restaurants. We love the casual vibe outside at Wahoos. We can't wait to go back. "