Chesapeake Resort

Looking for a charming stay in the Florida Keys? The Chesapeake Resort in Islamorada is a fantastic choice, offering a prime location in the Matecumbe area. You'll be right on the beach, perfect for soaking up the sun and enjoying the coastal atmosphere.

You'll find yourself conveniently close to some key attractions. The History of Diving Museum and the fascinating Windley Key Fossil Reef Geological State Park are both within a short, 5-minute drive. Plus, for those interested in local brews and history, the Islamorada Brewery & Distillery is just 1.2 miles away, and the Keys History & Discovery Center is a mere 1.7 miles from your doorstep.

At Chesapeake Resort, you can expect a relaxing beachside experience. While specific amenities aren't detailed here, the location itself is a major draw for those wanting to explore the beauty and history of Islamorada. We often find our rates here are more competitive than you might see on sites like Booking.com, Expedia, or LateRooms, and we proudly offer our Best Price Match guarantee, so you can book with confidence (prices may vary).

Ready to experience the laid-back vibe of Islamorada? Book your stay at the Chesapeake Resort today and discover all the Keys have to offer!