Find luxury hotels in Upper Matecumbe Key, FL

"Islander Resort is absolutely lovely. A devine get away in the midst of beautiful Islamorada."

"Great staff, very prompt"

"Amazing ! The private beach and amenities are incredible! "

"It was a beautiful property. The accommodations are a bit dated, but they seem to be renovating little by little. They have a sister property three waters and they offer free transportation so you can utilize both properties. It was very peaceful not overly crowded. I’d stay here again. "

"Great "

"This is my poace to go. Close convenient. Quiet, and the view is better than a 5 star hotel"

"All around, we gave it a 5. We really loved the fact that there are boat slips available on the property, it was very convenient for us, since we went out on the boat every day. Thank you!"

"Peaceful, beautiful and well-serviced rooms, pools, and resort in the Keys. Location in Islamorada is nicer than Key Largo and closer to airports than other Keys. Lots of restaurants nearby. "

"If you are traveling to the Florida Keys I recommend staying in Islamorada. The view from our room was amazing. What a beautiful piece of property the Chesapeake Beach Resort sits on. It was clean, the staff were great, the breakfast was delicious. Chris will cook you a good omelette. G Parker"