We have created a list with cool, unusual and unique hotels in Islamorada, USA. We have also included accommodation in boats, holiday homes, villas and romantic hotels. Hope you enjoy it. We think it might be the best of its kind around. Tip: Set your dates to see room prices!
A list by Ella Hofer & Maryna Kravets. Updated December 2023.
Holiday Home.Delightful property. Gorgeous surroundings. Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi. This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower. The holiday home includes a barbecue. There is a a terrace at this property and guests can go snorkelling, fishing and diving nearby. Two kayaks and 2 bicycles are offered. A boat hire is available for a surcharge. Theater of the Sea on Islamorada is 800 metres from Anglers Reef Paradise, while Upper Matecumbe Key is 5 km from the property.Show full description
In my judgement this could be one of the most BEAUTIFUL AND ROMANTIC holiday homes in Islamorada.
Resort.Charming. Great bar. Popular among couples. This Islamorada resort in the Florida Keys is located near Alligator Reef. It boasts an oceanfront freshwater pool, a Tiki Bar and a private beach area. This resort is less than 1.6 km from Miss Islamorada Fishing Charters. Each accommodation includes a full kitchen. A living area with a cable TV is included in all units at Pines & Palms Resort. The traditionally styled units feature light colours and island decor. Most offer a private terrace with ocean views. Guests at Resort Palms & Pines have access to kayak and bike rentals, private boat docks and premium sport fishing areas. A covered cabana with a barbecue grill, fridge and sink is available for guest use. The entrance to John Pennekamp Coral Reef State Park is less than 30 minutes’ drive away.Show full description
Based on my research this is one of the most CHARMING AND CREATIVE resorts in Islamorada.
Resort.Lovely property. Great bar. A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. Relax and enjoy beautiful views from fully furnished private porches or lanais. Spend the afternoon lounging by the Islander's 2 on-site swimming pools. Enjoy on-site dining at Beachside Bar and Grill. Easily discover a variety of activities only minutes from the Islander Resort, including snorkeling and scuba diving. Enjoy deep-sea fishing, sailing or browsing the local shops, also only a short distance away.Show full description
Villa.Highly elegant. Superb interior design. Featuring air-conditioned accommodation with a pool with a view, garden view and a patio, Anglers Reef Getaway is set in Islamorada. This beachfront property offers access to a balcony, squash on the squash court, free private parking and free WiFi. The property is non-smoking and is situated 600 metres from Windley Key. The villa with a terrace and pool views features 2 bedrooms, 2 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the villa. The property has an outdoor dining area. Guests can take advantage of the warm weather with the property's barbecue facilities. Guests at the villa will be able to enjoy activities in and around Islamorada, like fishing. Snorkelling and cycling can be enjoyed nearby, while a bicycle rental service and a private beach area are also available on-site. Upper Matecumbe Key is 5.5 km from Anglers Reef Getaway, while Pigeon Key is 16 km away. The nearest airport is Miami International Airport, 115 km from the accommodation.Show full description
Resort.Charming. Great value. Situated in Islamorada, 3.1 km from Windley Key, Ragged Edge Resort & Marina features accommodation with free bikes, private parking, an outdoor swimming pool and a terrace. Located around 8.3 km from Upper Matecumbe Key, the resort with free WiFi is also 14 km away from Pigeon Key. Some units at the property have a balcony with a sea view. Selected rooms also feature a kitchen with a fridge, an oven and a microwave. The resort offers a barbecue. Guests at Ragged Edge Resort & Marina will be able to enjoy activities in and around Islamorada, like fishing and cycling. John Pennekamp State Park is 27 km from the accommodation, while Windley Key Fossil Reef Geological State Park is 4.4 km from the property. The nearest airport is Miami International Airport, 113 km from Ragged Edge Resort & Marina.Show full description
Newly opened, August 2023. Boasting barbecue facilities, Treasure Harbor is situated in Islamorada in the Florida region, 2.9 km from Windley Key and 8.1 km from Upper Matecumbe Key. Featuring a terrace, the 3-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. Free private parking is available and the hotel also features bike hire for guests who want to explore the surrounding area. At the hotel, the rooms come with a balcony. Rooms are equipped with a coffee machine, while some rooms include a patio and others also boast lake views. All rooms in Treasure Harbor are fitted with a flat-screen TV and free toiletries. Guests at the accommodation will be able to enjoy activities in and around Islamorada, like cycling. Pigeon Key is 14 km from Treasure Harbor, while John Pennekamp State Park is 26 km from the property. The nearest airport is Miami International Airport, 113 km from the hotel.Show full description
Opened October 2020. Located in Islamorada, 1.7 km from Upper Matecumbe Key, The Islands of Islamorada provides accommodation with an outdoor swimming pool, free private parking, a fitness centre and a bar. This 4-star hotel offers a range of water sports facilities, a concierge service and free WiFi. Guests can use the hot tub, or enjoy sea views. The hotel will provide guests with air-conditioned rooms offering a wardrobe, a coffee machine, a fridge, a microwave, a safety deposit box, a flat-screen TV, a balcony and a private bathroom with a shower. Each room is equipped with a kettle, while some rooms are equipped with a kitchen with a dishwasher, an oven and a stovetop. At The Islands of Islamorada rooms are fitted with bed linen and towels. The accommodation offers a children's playground. Guests at The Islands of Islamorada will be able to enjoy activities in and around Islamorada, like snorkelling. Windley Key is 3.7 km from the hotel, while Pigeon Key is 20 km away. The nearest airport is Miami International Airport, 119 km from The Islands of Islamorada.Show full description
Hip. Great value. Located in Islamorada, less than 1 km from Upper Matecumbe Key, Sunset Inn provides accommodation with an outdoor swimming pool, free private parking, a garden and barbecue facilities. The 3-star hotel has air-conditioned rooms with a private bathroom and free WiFi. The property is non-smoking and is situated 4.5 km from Windley Key. All units at the hotel are equipped with a flat-screen TV with cable channels and a safety deposit box. Selected rooms are fitted with a kitchenette with a microwave. At Sunset Inn each room includes bed linen and towels. Pigeon Key is 21 km from the accommodation, while John Pennekamp State Park is 33 km away. The nearest airport is Miami International Airport, 120 km from Sunset Inn.Show full description
Perhaps this is the coolest small hotel in Islamorada.
Resort.Great views. Popular among women. This resort is situated on one-quarter mile of private beach on Long Key between Islamorada and Marathon. Bright spacious rooms and 2 swimming pools are available. Colorfully decorated rooms include flat-screen cable TVs. WiFi, a microwave and refrigerator are included in guestrooms. Guests can dock their boats (up to 21 feet) for free at the Lime Tree Bay Resort. A tennis court and a fishing dock are on site. Use of the sea kayaks, paddle boards, and barbecue facilities are offered. A sandy sunning beach with hammocks and loungers is available for guests' enjoyment. Pier 68 Boat Rentals is a 5-minute walk from the Resort Lime Tree Bay. Located on site, The Florida Boy Bar and Grill is open for breakfast, lunch, and dinner. Guests can relax in one of the many hammocks located on the property. Palm thatched huts are also on site.Show full description
Historic property. Popular among women. Offering an outdoor pool and sun terrace, Caloosa Cove Resort - With Full Kitchens is situated in Islamorada in the Florida Region, 9.6 km from Upper Matecumbe Key. Theater of the Sea on Islamorada is 18 km from the property. All units feature a flat-screen TV, a balcony with an ocean view, and fully equipped kitchen. Some units have 2 flat-screen TVs and 2 balconies with an ocean view. Unites also have 1 or 2 full bathrooms. Towels are exchangeable daily. Guests can enjoy a meal at the on-site restaurant. The property has a private beach area. The area is popular for fishing. Windley Key is 18 km from Caloosa Cove Resort - With Full Kitchens, while Windley Key Fossil Reef Geological State Park is 17 km away.Show full description
Based on my research this is the most HISTORIC small hotel in Islamorada.
Holiday Home. Situated in Islamorada and only 3.8 km from Windley Key, EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS features accommodation with sea views, free WiFi and free private parking. This holiday home offers a private beach area, a garden, as well as a tennis court. The property features a year-round outdoor pool with a pool bar and is set 9.1 km from Upper Matecumbe Key. Some units in the holiday home have private entrance and are fitted with desk and wardrobe. Some of the units have a satellite flat-screen TV, a fully equipped kitchen with a dishwasher, and a private bathroom with a walk-in shower and a hair dryer. In some units there is a dressing room for guests to change in. A bar can be found on-site, and in the warmer months you can make use of the barbecue facilities. The holiday home has a picnic area and a terrace. Pigeon Key is 13 km from EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS, while John Pennekamp State Park is 26 km from the property. The nearest airport is Miami International Airport, 112 km from the accommodation.Show full description
We try to keep this list as up-to-date as possible. We last updated it in December 2023. Help us make this page better, for example by letting us know of a unique hotel that should be on the list. Click here to get in touch. Thanks!
Check out these other cool hotel lists for Islamorada: