Find 2-Star Hotels in Islamorada

Welcome to Three Waters Resort & Marina, a one-of-a-kind destination named for the rare meeting of the Atlantic Ocean, Florida Bay, and the Gulf of Mexico. Set on 15 waterfront acres in Islamorada—the “Sportfishing Capital of the World”—our resort blends island adventure with serene relaxation. Relax in a range of island-inspired guestrooms and cottages, or retreat to The Cove, our adult-focused oasis with a private beach lagoon. Discover tropical beauty and the spirit of the Florida Keys, plus nine unique dining options—from the wood-fired warmth of Kindler to the iconic Tiki Bar. Cruise between experiences aboard our water taxi, Rum Runner. At our full-service marina, a seasoned fleet of captains welcomes anglers of every level. Whether you’re seeking world-class fishing, a family vacation, romantic escape, upscale retreat, or a dream beach wedding, Three Waters Resort & Marina is your ultimate Florida Keys escape.

Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park. This beach hotel is 1.2 mi (2 km) from Islamorada Brewery & Distillery and 1.7 mi (2.8 km) from Keys History & Discovery Center. Spend the day on the private beach or dip into one of the 2 outdoor swimming pools. This hotel also features complimentary wireless internet access and concierge services. Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 6:00 AM to 10:00 AM. Featured amenities include a computer station, a 24-hour front desk, and multilingual staff. Make yourself at home in one of the 60 air-conditioned rooms featuring microwaves and flat-screen televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, designer toiletries, and hair dryers.

With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center. This hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from History of Diving Museum. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a picnic area. The front desk is staffed during limited hours. Limited parking is available onsite. Make yourself at home in one of the 20 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with showers are provided. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park. This beach aparthotel is 1.3 mi (2.1 km) from Hurricane Monument and 1.5 mi (2.4 km) from Florida Keys Brewing Co.. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. This aparthotel also features complimentary wireless internet access, gift shops/newsstands, and tour/ticket assistance. Featured amenities include luggage storage, laundry facilities, and a safe deposit box at the front desk. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 40 guestrooms, featuring kitchens with full-sized refrigerators/freezers and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided weekly.

Located in Islamorada (Matecumbe), Sands of Islamorada is within a 5-minute drive of Bud n' Mary's Dive Center and History of Diving Museum. This hotel is 4.7 mi (7.5 km) from Windley Key Fossil Reef Geological State Park and 6.6 mi (10.6 km) from Anne's Beach. Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include laundry facilities and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 9 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include safes and microwaves, and housekeeping is provided daily.

With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the Strip, just steps from Windley Key Fossil Reef Geological State Park and a 3-minute drive from History of Diving Museum. This beach hotel is 2 mi (3.3 km) from Rain Barrel Village and 2.2 mi (3.5 km) from Founders Park. Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional features at this hotel include complimentary wireless internet access, wedding services, and a picnic area. A complimentary continental breakfast is served daily from 9:00 AM to 11:00 AM. Featured amenities include a business center, complimentary newspapers in the lobby, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 20 guestrooms featuring refrigerators and microwaves. Rooms have private patios. 24-inch LCD televisions are provided, with cable programming available. Bathrooms have complimentary toiletries and hair dryers.

When you stay at Ragged Edge Resort & Marina in Islamorada, you'll be near the beach, within a 10-minute walk of Rain Barrel Village and Founders Park. This guesthouse is 0.6 mi (0.9 km) from Islamorada County Park and 2.1 mi (3.4 km) from Windley Key Fossil Reef Geological State Park. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. Additional features at this guesthouse include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include express check-in, express check-out, and laundry facilities. Free self parking is available onsite. Make yourself at home in one of the 14 guestrooms. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include ceiling fans, and housekeeping is provided daily.

With a stay at Treasure Harbor in Islamorada, you'll be within a 10-minute walk of Rain Barrel Village and Founders Park. This hotel is 0.5 mi (0.8 km) from Islamorada County Park and 2 mi (3.2 km) from Windley Key Fossil Reef Geological State Park. Make use of convenient amenities, which include complimentary wireless internet access and a vending machine. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 6 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and hair dryers. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided once per stay.

Located in Islamorada (Matecumbe), Matecumbe Resort is within a 5-minute drive of Robbie’s of Islamorada and Indian Key Historic State Park. This beach resort is 1.9 mi (3 km) from Sunset Drive Beach and 2.9 mi (4.6 km) from Anne's Beach. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool. Additional amenities at this resort include complimentary wireless internet access, a picnic area, and charcoal grills. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 36 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and microwaves, and housekeeping is provided on request.