Chesapeake Beach Resort

We decided to break up the drive from Key West to home. I went online and found the Chesapeake and booked it immediately. It was great. We are already planning on staying there again.

LOVED every minute I spent there and cannot wait to go back again! Had stayed here in 1992 before the renovation and was delighted and amazed at the updates, the kayaks and other activities on site, as well as how immaculate the room and grounds were. Most important positive of all is that every single member of the staff was lovely in all respects and went out of their way to help everyone. This is a great location and Islamorada has always been a favorite, with all of the very best and most classic Keys specialties - the people, experiences, and visitors who take care of all of the treasures so well.

Beautiful location with private beach. Very calm and casual. 2 pools are lovely Recently upgraded. Very comfortable bed and nice people at front desk. The chef at the omelette station in the morning is gruff and unfriendly, which isn’t in tune with the vibe of this little gem. If you are looking for a laid back experience in a lovely atmosphere then you are in the right place. They also have BYOB tiki huts seating 6 that will motor you out to the sandbar for a few hours.

Great place. Nicely decorated, very clean, beautiful ocean views. Vanesa at the office was terrific. Nice staff and very welcoming. Nice clean pools to use. Would highly recommend and would certainly return there. You will enjoy your stay.

We recently spent three nights at this resort and loved the location and beautiful property. It felt very private and secluded on the beach and pool area. The grounds were clean and most of the staff we interacted with were helpful and friendly. Our main issue with the hotel was the bugs in the rooms. On our first night as we were getting into bed after a very long travel day (leaving our house at 2:30 am), we noticed multiple roaches on the floor and were able to trace them back to a crack in the wall. We alerted the front desk and switched rooms in our pajamas which involved packing all of our bags again. We requested multiple times to speak with a manager and were told she was not onsite and would call us. We were offered a villa by the desk staff, however this had smaller beds. On our last night we again had a large bug in our room at night. Their water sports equipment (kayaks and paddle boards) are also in poor shape with broken paddles and a broken kayak that takes in water. We are sad to leave this review because overall the resort is a lovely little spot with mostly pleasant staff, just a few things to work on.