Popular Islamorada 4-star Hotels

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 Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and 13 minutes by foot from Indian Key Historic State Park. This beach resort is 1.4 mi (2.3 km) from Hurricane Monument and 1.6 mi (2.5 km) from Florida Keys Brewing Co..Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and a fitness center. This resort also features wireless internet access (surcharge), gift shops/newsstands, and wedding services. Getting to nearby attractions is a breeze with the complimentary area shuttle that operates within 4.00 mi.Grab a bite at ReelCatch, one of the resort's 2 restaurants, or stay in and take advantage of the room service (during limited hours). Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 6:00 AM to 11:00 AM for a fee.Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 110 air-conditioned rooms featuring flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Wireless internet access (surcharge) is available to keep you connected. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.

With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi (1.7 km) from Hurricane Monument and 1.3 mi (2.1 km) from Florida Keys Brewing Co..Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and bicycles to rent. Additional amenities at this resort include wireless internet access (surcharge), wedding services, and a picnic area. Guests can catch a ride to nearby destinations on the complimentary area shuttle.Take advantage of the resort's room service (during limited hours). Quench your thirst with your favorite drink at the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 11:00 AM for a fee.Featured amenities include a 24-hour front desk and a water dispenser.Make yourself at home in one of the 55 individually decorated guestrooms, featuring kitchenettes with refrigerators and microwaves. Your pillowtop bed comes with Egyptian cotton sheets. Wireless internet access (surcharge) keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, as well as safes and desks.

With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery & Distillery. This beach hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.2 km) from Florida Keys Brewing Co..Practice your swing on the golf course or soak up the sunshine on the private beach. Additional features at this hotel include complimentary wireless internet access, gift shops/newsstands, and wedding services.Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. When you are in need of a refreshing drink, visit the beach bar or one of 2 bars/lounges, or 2 poolside bars. Full breakfasts are available daily from 7:00 AM to noon for a fee.Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Planning an event in Islamorada? This hotel has 2760 square feet (256 square meters) of space consisting of a conference center and 4 meeting rooms. Free self parking is available onsite.Make yourself at home in one of the 114 guestrooms featuring iPod docking stations and 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 The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. This beach villa is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1.1 mi (1.8 km) from Matecumbe United Methodist Church.Dip into one of the 2 outdoor swimming pools or enjoy other recreational amenities including a 24-hour fitness center and a pickleball court. This villa also features complimentary wireless internet access, concierge services, and wedding services.Wrap up your day with a drink at the poolside bar.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers.

A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, just a 3-minute walk from Windley Key Fossil Reef Geological State Park and within a 5-minute drive of Rain Barrel Village. This beach motel is 1.9 mi (3.1 km) from History of Diving Museum and 2 mi (3.2 km) from Founders Park.Relax on the private beach or enjoy other recreational amenities such as an outdoor pool. Additional amenities at this Art Deco motel include complimentary wireless internet access, concierge services, and gift shops/newsstands.A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.Featured amenities include express check-out, luggage storage, and coffee/tea in a common area. Free self parking is available onsite.Make yourself at home in one of the 22 individually decorated guestrooms, featuring refrigerators and microwaves. 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 coffee/tea makers and irons/ironing boards, and housekeeping is provided on request.

With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. This beach hotel is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1 mi (1.6 km) from Matecumbe United Methodist Church.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 gift shops/newsstands.A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM.Featured amenities include express check-out, multilingual staff, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 37 air-conditioned rooms featuring refrigerators. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.

With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center. This beach hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.9 mi (1.4 km) from Florida Keys Brewing Co..Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool. Additional features at this hotel include complimentary wireless internet access and concierge services.Grab a bite from the snack bar/deli, or stay in and take advantage of the hotel's room service (during limited hours). Relax with your favorite drink at the bar/lounge or the poolside bar. A complimentary continental breakfast is served daily from 7 AM to 11 AM.Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and luggage storage. Free self parking is available onsite.Make yourself at home in one of the 16 individually decorated guestrooms, featuring minibars and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.

With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum.Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills.Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite.Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and 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 bidets. Conveniences include laptop-compatible safes and coffee/tea makers, and housekeeping is provided daily.

With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Rain Barrel Village. This hotel is 1.9 mi (3 km) from Founders Park and 1.9 mi (3 km) from Islamorada County 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.