The Best Hotels
with Pool in Islamorada

Resort with outdoor pool. Charming. 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

Resort with outdoor pool. Charming. 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. 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. This resort is less than 1.6 km from Miss Islamorada Fishing Charters. The entrance to John Pennekamp Coral Reef State Park is less than 30 minutes’ drive away. Show full description

Resort with outdoor pool. Cosy rooms. 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

Resort with outdoor pool. Delightful property. 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

Resort with outdoor pool. Great views. Located adjacent to Windley Key Fossil Reef Geological State Park, this Islamorada resort features an ocean-side outdoor swimming pool. Beach towels, Kayaks, Paddle-boards & WiFi are included at this oceanfront resort and marina. A microwave, refrigerator and coffee-making facilities come standard in each a room at Drop Anchor Resort & Marina Resort and Marina. A flat-screen TV is also included. Trailer parking and boat docking are possible at Drop Anchor Resort & Marina Resort. Barbecue facilities, outdoor dining areas and hammocks are available as well. Theater of the Sea is just 9 minutes’ walk from Drop Anchor Resort & Marina Resort and Marina. Guests will be 6.9 miles from Indian Key Historic Park. Show full description

Resort with outdoor pool. Cosy rooms. Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away. Chesapeake Beach Resort boasts an outdoor pool with an ocean view. A 37-inch flat-screen cable TV and a small refrigerator are offered in each room at this Florida Chesapeake Beach Resort. Select rooms and suites have a balcony. Guests can check out the History of Diving Museum (3 minutes’ walk) or see a show at the Theater of the Sea (4 minutes’ drive). Show full description

Small hotel with outdoor pool. 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

Small hotel with outdoor pool. Trendy. 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

Resort with outdoor pool. Elegant. Located on the waters of the Florida Bay, the Islander Bayside Resort is less than 5 minutes’ walk from the beach. This resort features a kitchen in every townhouse and an outdoor pool. A flat-screen TV is included in every guest townhouse of this Islamorada resort and all units have free WiFi and laundry facilities. Kitchens offer a microwave, refrigerator and an oven. Bicycle rental is possible on site and various water sport activities are located nearby. There are various dining options less than 1.6 km from this resort and Windley Key Fossil Reef Park is 5 minutes’ drive away. Long Key is 15 minutes’ drive from the property. Show full description

Outdoor pool. Unique. Just off the Overseas Highway and in front of the ocean, this Islamorada hotel offers an on-site marina. The beachfront hotel features an outdoor pool. WiFi is included in the resort fee. The suites and cottages at La Siesta Resort & Villas are equipped with a cable TV and air conditioning. On site, Wild and Lime bar serves light fares, beer, and wine daily. Activities such as boating, fishing, jet skiing and snorkeling can be arranged. The on-site marina offers both gulf-side and ocean-side slips while non-motorized watersports equipment and bicycles are provided for guests' use. Theater of the Sea is 6 km away from the accommodation while Anne's Beach is located 10.8 km away. Show full description

Outdoor pool. Cool. Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games on the property. Free Wi-Fi is included in all rooms of this Islamorada hotel and guests can also enjoy cable TV in the rooms. Some units offer a kitchenette so guests can prepare their own meals during their stay. A launderette is available on site at the Fisher Inn Resort & Marina. Guests will also be able to enjoy various activities such as fishing, windsurfing, kayaking, paddle boarding and snorkeling during their stay. This oceanfront hotel is less than 10 minutes’ walk from the Theater of the Sea. The Holiday Isle Marina is also less than 1 mile away. Show full description

Outdoor pool. Unique. This beachfront hotel is located in Islamorada, Florida and features transfer services within 6 km from the property. WiFi is included in the resort fee. Guests can relax on beachside hammocks or enjoy the outdoor pool at Amara Cay Resort. An on-site fitness centre is available, as well as a meeting space. A flat-screen TV, work desk, and safety deposit box comes standard in every guestroom. Bicycle rentals and luggage storage are offered on site. Sample a custom cocktail at the Tiki Bar or experience Amara Cay Resort’s restaurant, ReelCatch. The History of Diving Museum is 4.9 km away. Guests will be 8 minutes’ drive from Anne’s beach. Windley Key Fossil Reef Geological State park is 8 minutes’ drive. Show full description

Resort with outdoor pool. Highly elegant. Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spais a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot fishing pier. Adult and family-style swimming pools can be enjoyed at the resort. Each guestroom includes dark hardwood furniture and a balcony with views of the resort. Guests can watch movies on the 42-inch flat-screen TV with DVD player or browse the internet with free WiFi. An in-room safe and coffee maker are also provided. Additionally, a fully equipped fitness centre, 6 tennis courts, and a full-service watersports facility are open to guests. Three restaurants and a tiki bar are located on-site at Cheeca Lodge & Spa. Atlantic’s Edge offers tropically-inspired cuisine amid a classic décor while Nikai Sushi Bar & Restaurant serves nigiri, sashimi, and more. Downtown Key Largo is a 20-minute drive from Cheeca Lodge & Spa. Long Key State Park is 13.7 miles from the resort. Show full description

Resort with outdoor pool. Luxurious. Featuring a unique tropical atmosphere and situated on an island in the Florida Keys, this resort offers WiFi and parking to guests. A cable TV and a private bathroom are included in every guestroom. A safety deposit box is also provided. Guests of Postcard Inn Beach Resort & Marina can stop by the marina to charter a fishing trip or rent a jet ski. Guests seeking adventure will enjoy snorkeling and diving charter boats. Windley Key Fossil Reef Geological Park is just 3 minutes’ drive from the property while Key Largo is 21 minutes’ drive. Facilities at this hotel include swimming pool. Show full description

Small hotel with outdoor pool. This hotel is located in Islamorada, Florida. Hadley Resort and Marina features an outdoor swiming pool and free WiFi throughout the property. Some rooms also have sea views or pool views. Each room at the Hadley Resort and Marina features a private bathroom, a kitchenette with a refrigerator and a microwave. Other facilities offered at the property include dock space and a marina. A dock and a marina are offered at the property. The Theater of the Sea is located 2.9 km from the hotel, the Tiki Bar at Holiday Isle is 2.4 km away, and Founders Park Watersports is 7.7 km from the property. Show full description

Apartment hotel with outdoor pool. Very stylish. Situated 1.9 km from Sea Oats Beach, Matecumbe Resort offers 2-star accommodation in Islamorada and has a private beach area, an outdoor swimming pool and a garden. This beachfront property offers access to table tennis, free private parking and free WiFi. Some units have a terrace and/or a patio with sea or pool views. The property offers allergy-free units and is located 9.2 km from Upper Matecumbe Key. The aparthotel provides guests with a balcony, garden views, a seating area, cable flat-screen TV, a fully equipped kitchen with an oven and a microwave, and a private bathroom with shower and a hair dryer. At the aparthotel, every unit is fitted with bed linen and towels. For those times when you'd rather not dine out, you can choose to cook on the barbecue. Guests at the aparthotel will be able to enjoy activities in and around Islamorada, like cycling and fishing. Matecumbe Resort features a children's playground and a picnic area. Windley Key is 14 km from the accommodation, while Pigeon Key is 30 km from the property. The nearest airport is Key West International Airport, 118 km from Matecumbe Resort. Show full description

Inn / Guest House with outdoor pool. Unique. This Islamorada, Florida inn boasts an outdoor pool with a hot tub and a boat dock with a ramp. Guests will be 4 miles from Theater of the Sea and 2 miles of Indian Key Historic State Park. Free Wi-Fi, a microwave, and a small refrigerator are included in all rooms. A kitchenette, balcony, and sofa bed are featured in select studios at this Florida Sands of Islamorada property. Guests can lounge in the hot tub throughout their stay at Sands of Islamorada. Drink and snack vending machines as well as free on-site parking are offered. The History of Diving Museum is 3 miles away. Guests will also be 3 miles from Lignumvitae Key Botanical State Park. Show full description

Inn / Guest House with outdoor pool. Hip. Featuring free WiFi and an outdoor pool, La Jolla Resort offers accommodation in Islamorada, 800 metres from Upper Matecumbe Key. Free private parking is available on site. All rooms include a flat-screen TV. Every room comes with a private bathroom fitted with a shower. Extras include free toiletries and a hair dryer. There is a shared lounge at the property. This inn has a private beach area. You can engage in various activities, such as cycling and fishing. Theater of the Sea on Islamorada is 3.7 km from La Jolla Resort, while Windley Key is 4.3 km from the property. Anne's Beach is 11 minutes' drive. Show full description

Holiday Home with outdoor pool. 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

Inn / Guest House with outdoor pool. Located in Islamorada, Florida, this beachfront inn offers an outdoor pool and a private beach area. A marina is on site as well. A microwave and refrigerator are available in each room at Coconut Cove Resort and Marina. A flat-screen TV is included. Select rooms feature a full kitchen. Boat docking facilities are available for a surcharge. At Coconut Cove Resort & Marina guests will find a fitness centre and vending machines. The inn is 7 minutes’ walk from Theater of the Sea on Islamorada, 600 m from Windley Key Fossil Reef Geological State Park. Show full description