Resorts in Islamorada

Welcome to Cheeca Lodge & SpaTurquoise water. Towering palms. Calm breezes. Imagine yourself whisked away to a tropical paradise where you indulge in mind, body, and spirit, as you rediscover an oasis called Cheeca Lodge & Spa. Romantic, serene, and dynamic, our Florida Keys Islamorada resort is a standard of excellence achieved by few. Be swept away by the casual elegance emanating from every detail and settle into the laid-back lifestyle of Islamorada.Stay in the Sportfishing Capital of the WorldLocated in the Sportfishing Capital of the World, Cheeca Lodge is a premier destination for serious anglers. Charter a boat and find over 500 species of fish within minutes from shore. The casual fisherman can cast a line from the end of our 525-foot pier – the longest in the Keys. A host of other activities can be found at our Islamorada luxury resort, including snorkeling, sea kayaking, bicycling, and scuba diving. Between activities, enjoy first-class dining at one of our three restaurants: Atlantic’s Edge, Mia Cucina, or Nikai Sushi.

With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 4 minutes by foot from Lorelei Restaurant & Cabana Bar. This beach hotel is 0.4 mi (0.7 km) from Islamorada Brewery & Distillery and 0.4 mi (0.7 km) from Matecumbe United Methodist Church. Spend the day on the private beach or dip into one of the 2 outdoor pools. Additional features at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. Relax with a refreshing drink at the beach bar, the poolside bar, or one of 2 bars/lounges. Full breakfasts are available daily from 7:00 AM to 11:00 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Event facilities at this hotel consist of a conference center and 13 meeting rooms. Free self parking is available onsite. Stay in one of 114 guestrooms featuring Smart televisions. Rooms have private lanais. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.

With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 3-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center. This beach hotel is 1 mi (1.6 km) from Hurricane Monument and 1.2 mi (1.9 km) from Florida Keys Brewing Co.. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and wedding services. Take advantage of the hotel's room service. Need to unwind? Take a break at the bar/lounge, the beach bar, or the poolside bar for a tasty beverage. Featured amenities include limo/town car service, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 26 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. 50-inch flat-screen televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.

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 1.6 mi (2.6 km) from Hog Heaven. 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.

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 (2.7 km) from Lorelei Restaurant & Cabana Bar. Spend the day on the private beach or dip into one of the 2 outdoor 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 Bayside Villas by Islander Resort, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co.. This beach hotel is 0.4 mi (0.7 km) from MoradaWay Arts & Cultural District and 0.5 mi (0.8 km) from Indian Key Historic State Park. Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Getting to nearby attractions is a breeze with the complimentary area shuttle that operates within 1.5 miles. Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. Quench your thirst with your favorite drink at the bar/lounge. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 25 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies. 55-inch LCD televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected.

With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, just a 4-minute walk from Windley Key Fossil Reef Geological State Park and 7 minutes by foot from Hog Heaven. This hotel is 1.7 mi (2.8 km) from Rain Barrel Village and 1.9 mi (3 km) from Founders Park. 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. This Art Deco hotel also features complimentary wireless internet access, wedding services, and a picnic area. Featured amenities include a business center, a safe deposit box at the front desk, and coffee/tea in a common area. Free self parking is available onsite. Make yourself at home in one of the 18 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.