Welcome to the Chesapeake Resort, a carefree island getaway located on Islamorada in the breathtaking Florida Keys. Situated just two hours south of Miami on 6½ oceanfront acres, our Tommy Bahama-style retreat presents luxurious oceanfront or garden-view accommodations which pamper guests with outstanding amenities. Surrounded by lush tropical beauty and sparkling blue waters legendary for fishing and snorkeling, the Chesapeake Resort has offered guests an array of island adventures for over 50 years.

Experience the excitement of exotic coral and colorful marine life at our very own Rainbow Reef, one of the world's top rated dive centers. Charter a boat for an expedition in the “Sport Fishing Capital of the World.” Or just sip a cool drink by our oceanfront swimming pool and Jacuzzi. Nearby, explore quaint shops, and famed attractions such as the Windley Key Geological Park and The Wild Bird Sanctuary. When it’s time for some refreshment, head to our signature restaurant, the Spoonbill Cafe, for a true taste of island cuisine.

• 68 Guest Rooms, Suites & Villas
• Beautiful Oceanfront & Garden Views
• Located 2 Hours South of Miami
  (Between Miami & Key West)
• 2 Oceanfront Freshwater Pools
• Rainbow Reef Dive Center
• Watersports Facility
• Lagoon
• Marina w/ 17 Boat Slips
• Tennis Court
• Function Space
• Tropical Garden
• Restaurant & Bar (Spoonbill Cafe)