Islamorada is our favorite island and we've been staying here off and on for about ten years. I know all the hotels as the island is not that big, and you will end up bicycle riding through each one of them sooner or later. I think one of the best places is the Chesapeake Resort. The location is great for taking advantage of Islamorada's famous things to do. This is a beach and fishing destination hotel, just perfect for a super Florida Keys weekend getaway. If you have a boat, your best bet is to stay at the La Siesta Resort loaded with amenities, and a nice on property boat ramp. The resort is just a super spot for an extended stay along the beachfront. Another great one for the boater is Pines and Palms Resort. One great thing about staying in Islamorada, is almost all of the island's hotel are on the water. We love a place that has everything you need to enjoy the ocean and fishing. If you want to stay on the sunset side of the island, go with the Kon Tiki Resort. These Cottages are a perfect place to stay in the upper Florida Keys. A nice home-base whether you want to snorkel, fish all day, or just relax and enjoy the views!