CHESAPEAKE BEACH RESORT, Islamorada

Chesapeake Beach Resort offers a private beach area with loungers exclusively for guests. Complimentary kayaking and paddleboarding are included in the stay, with equipment available for daily use. Two heated outdoor pools, one with ocean views, and a hot tub provide additional relaxation options, while yoga classes and live music performances are scheduled on-site.

Guests can choose from spacious two-bedroom villas or premium villas, many with ocean views and private balconies. Each room includes a 37-inch flat-screen cable TV, a small refrigerator, and select rooms offer a balcony. The property is pet-friendly, allowing pets in designated accommodations, and wheelchair-accessible rooms feature raised toilets, grab rails, and Braille visual aids.

A complimentary breakfast is served daily until 11:00 AM, featuring made-to-order omelets, pancakes, and French toast alongside a continental buffet. The on-site restaurant offers a snack bar and serves wine and champagne, with a small bar for drinks throughout the day. Personalized breakfast delivery service is available for guests staying in villas, ensuring a relaxed start to the day.

The resort is located on the oceanfront along Highway 1 in Islamorada, with the History of Diving Museum a 3-minute walk away. Windley Key Fossil Reef Geological State Park is 2 miles from the property, and Theater of the Sea is a 4-minute drive. Several restaurants and a supermarket are within walking distance, and a free city cab service provides local transportation.

Private beach: Exclusive guest-only loungers and beach area

Water sports: Complimentary kayaks, paddleboards, and fishing poles

Breakfast: Made-to-order omelets, pancakes, French toast until 11 AM

Villas: Two-bedroom and premium villas with ocean views and balconies

Pet-friendly: Pets allowed in designated rooms

Location: Steps from History of Diving Museum, 2 miles from Windley Key State Park