Discover the beauty and allure of Islamorada’s legendary beach and fishing destination – the Chesapeake Beach Resort. Lose yourself amidst swaying palm trees, endless ocean vistas, flowering hibiscus, exotic birds, and a lush private lagoon. A 6.5-acre oceanfront property, our Islamorada hotel offers a tranquil sanctuary of sparkling white sands and tropical gardens— the perfect island getaway. Select one of our 65 guest rooms and suites, which feature luxurious tropical decors and amenities like complimentary Wi-Fi, private balconies with amazing views of the deep-blue waters outside and tropical gardens. For more than 50 years, the Chesapeake Beach Resort has welcomed generations of families, group tours, adventurers, and sport-fishing enthusiasts. It’s easy to see why when you take advantage of our recreational choices. Enjoy our two heated oceanfront pools, soaking spa, and tennis and shuffleboard court. Charter a boat for deep-sea or back-country fishing, or plan a day of snorkeling or diving. The friendly staff at our Islamorada hotel is here to make your stay a wonderful and memorable experience. Whether you’re planning a unique corporate gathering or group retreat, a romantic escape for two, or a fun family vacation, we’ll fit your lifestyle and needs. Anything is possible at Islamorada’s most famous beach and fishing resort. Come slip away with us.