Chesapeake Beach Resort

Chesapeake Beach Resort boasts an unbeatable oceanfront location in Islamorada with breathtaking views of the Atlantic and a beachfront setting. The resort’s private beach invites families to paddle, swim, or try complimentary kayaks and paddle boards, while shaded lounging spots make it easy to relax between adventures. Popular family destinations are within easy reach: the History of Diving Museum is a short stroll away and the Theater of the Sea offers quick, entertaining outings just minutes from the resort. The neighborhood also puts waterfront restaurants within walking distance, making meal times both convenient and scenic for guests with large groups.

Mornings start with a complimentary continental breakfast so everyone heads out fueled and happy. Two outdoor swimming pools overlook the ocean, providing plenty of space for kids to play while parents enjoy the views. The spacious Premium 1-Bedroom Ocean View Villas and Two-Bedroom Villas each offer flexible sleeping options for families with 3 or 4 kids. These accommodations include multiple beds and a living room with a sofa bed, so everyone can spread out, unwind, and enjoy plenty of privacy after a full day on the water.

Two-Bedroom Villa: Accommodating up to 6 guests, this villa features a king bed in one bedroom, a full bed in the second bedroom, and a sofa bed in the living room. Spacious and comfortable, it comes with a flat-screen TV, complimentary Wi-Fi, a small refrigerator, and plenty of room for families with 3 or 4 kids.

Premium One-Bedroom Ocean View Villa: This roomy villa sleeps up to 6 and is ideal for families of 5 or 6, with two full beds in the bedroom and a sofa bed in the living room. The villa includes a flat-screen TV, complimentary Wi-Fi, and a small refrigerator, offering comfort and convenience for large families.