4 Star Hotels in Islamorada

5 Stars... it was great, and it all started with the extraordinary reception and welcoming by Dusti Rose 🌹 at the front desk. She was warm, friendly, personal, and extremely nice. She answered any and all questions and provided information on the hotel and Islamorada... just a great welcoming experience.. She was superb, to say the least. Thank you, Dusti and the Islander. We'll definitely be coming back.

We stopped for one night on our way to Key West. I wish we booked more nights here. We had a great stay. Aaron at the front desk was extremely helpful at checkin. He was very friendly and personable. This hotel is lucky to have him as a part of their front desk team. The lobby was beautiful with great views. We had a lot of fun playing with the complimentary games provided. We spend most of our time at the pool, which was large and lovely. Great views. The Tiki Bar made awesome drinks, one of the best pina colada’s that I ever had. We ate dinner there too, which worked out so well because our kids could keep playing at the pool and we all had fun after playing games outside. Room was large and comfortable. Breakfast the next day…really good! Try the breakfast panini sandwich, you won’t regret it! I see people talking about the resort fee. When you consider this hotel doesn’t charge for parking or wifi, offers complimentary kayak and paddle board rentals, a shuttle between their hotel and sister hotel with access to these amenities too… the resort fee is not so expensive. I’ve stayed at hotels with resort fees that charge extra for parking and internet, and include NO amenities except access to a pool and workout facility. At least this hotel gives you something for the money you spend. Thank you for a great stay, we will absolutely be back. For longer next time!

Great trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifi

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 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, which include a 24-hour fitness center. 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.

The reception staff were lovely, so welcoming and helpful. Little heated pool and nice sun loungers, just missing some umbrellas to make it perfect. The outside grill was great to use and clean. Room didn’t get cleaned during our two night stay though… 🤷🏼♀️

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, complimentary newspapers in the lobby, and a safe deposit box at the front desk. 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.