Islamorada's beachfront hotels are spread across Upper Matecumbe Key and Windley Key, offering direct access to the Atlantic Ocean or Florida Bay. Guests can expect private beaches, outdoor swimming pools, and complimentary water sports equipment such as kayaks and paddleboards. Budget-friendly options like La Jolla Resort start around $150 per night, while luxury properties like Cheeca Lodge & Spa exceed $400. Most hotels provide free WiFi and parking; some include resort fees covering bikes and boat rentals.
Top-rated hotels include Cheeca Lodge & Spa, a 27-acre luxury resort with a 9-hole golf course, full-service spa, and 525-foot fishing pier. Three Waters Resort & Marina features three pools, kids' activities, and an adults-only enclave called The Cove. Casa Morada, a 5-star boutique hotel, offers free bikes, a hot tub, and a buffet breakfast. Chesapeake Beach Resort provides ocean-view rooms with two pools and is within walking distance of the History of Diving Museum. For a budget stay, La Jolla Resort has a private beach and free parking.