Chesapeake Beach Resort is a 3-star beachfront retreat in Islamorada, Florida, United States, located about 1.2mi from the city center. Address: 83409 Overseas Highway. The resort offers breakfast and sits right on the private beach, providing easy shoreline access and a classic tropical vibe.

Amenities abound with a private beach area (free) and an outdoor swimming pool (free), plus private parking on site (free) and free Wifi. Other conveniences include a private entrance, balcony, kitchenette with kitchenware, elevator access to upper floors, air conditioning, and a 24-hour front desk for a smooth stay. The property is pet-friendly with extra charges and is equipped for non-smoking stays and wheelchair accessibility. Reviews: 853. Price starts from $387.

On a sunny day, sun loungers line the beach as waves lap the shore, while the private parking and easy access from Overseas Highway make outings simple—an inviting base for beach lovers seeking comfort and convenience.

Stepping onto the private shoreline feels like stepping into a sunlit postcard, with easy beach access and a true tropical vibe. Private parking on site and smooth access from Overseas Highway keep day trips simple, while many dwellings offer a balcony and a kitchenette with kitchenware for easy in-room dining. Elevators make it a breeze to reach upper floors, and air conditioning keeps comfort high after a day in the sea breeze.

Two outdoor pools provide a cool contrast to sun and surf: both are heated and adults-only, with shallow ends and views that make a splashing good backdrop for a relaxed afternoon. The pools are part of year-round availability, and handy services like a 24-hour front desk can help with recommendations or last-minute plans, ensuring nothing interrupts the salt-air soaks.

Pets are welcome with possible extra charges, and the property supports non-smoking stays while offering wheelchair accessibility for easy exploration of the grounds. Free WiFi helps keep travel updates and photos flowing, making it simple to share every sunset and seaside find along the way.