Chesapeake Beach Resort

On Islamorada’s sun-soaked Matecumbe stretch in the Florida Keys, halfway between Miami and Key West. This oceanfront resort sits on 6.5 acres with a private beach and is about 2 km (1.2 miles) from the town center and nearby sights like the History of Diving Museum. Pet-friendly and family-friendly, it’s an easy launchpad for Keys adventures.

The property has 60 air-conditioned rooms with pillowtop beds and flat-screen TVs. Rooms include microwaves, mini-refrigerators and coffee makers; bathrooms come with tubs or showers, hair dryers and designer toiletries. Some rooms can sleep three to four guests using existing bedding, so it works well for families.

Two outdoor pools, a private beach, a tennis court and access to water sports (extra charge). There’s a children’s play area, free on-site parking, guest laundry (extra charge) and concierge service. Wake up to sea-breeze mornings and rinse off by the pool after a day on the water.

Complimentary Wi‑Fi across the property, a computer station and a 24-hour front desk with multilingual staff to help with arrangements.

An on-site restaurant and bar/lounge keep things simple and social. A complimentary continental breakfast is served daily from about 6:00 AM to 10:00 AM to fuel early fishing or island exploring.