Hotels on the beach in Islamorada, United States
Hey! I love staying in a nice beachfront hotel - being able to go straight from your room down to the ocean is a priceless feeling. To help save some time when booking your next vacation I've put together this list of beach hotels and resorts in Islamorada. I hope you will like it!
This page was last updated in June 2026.
The List 6 Amazing Beach Hotels in Islamorada
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1 Caloosa Cove Resort by CoolVacay
Islamorada
Offering an outdoor pool and sun terrace, Caloosa Cove Resort by CoolVacay is located in Islamorada in the Florida Region, 6 mi from Upper Matecumbe Key. Theater of the Sea on Islamorada is 11 mi from the property. All units feature a flat-screen TV, a balcony, 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. Even though this is a beachfront resort not every room has a water view. 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 11 mi from Caloosa Cove Resort by CoolVacay, while Windley Key Fossil Reef Geological State Park is 11 mi away. Construction Notice: Ongoing work on the property may cause daytime noise. We appreciate your understanding.
Address 73801 Overseas Highway Show on map- Heated pool
- Tennis court
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2 Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Featuring a unique tropical atmosphere and located 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 in-room safes is also provided. Guests of Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 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.
Address 84001 Overseas Highway Show on map- Heated pool
- Water sports facility
- Gym / fitness center
- Pets are welcome
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3 Chesapeake Beach Resort
Islamorada
Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away. 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. Chesapeake Beach Resort features an outdoor pool with an ocean view. 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).
Address 83409 Overseas Highway Show on map- Heated pool
- Pets are welcome
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4 Pelican Cove Resort & Marina
Islamorada
Located in Islamorada in the Florida Keys, this property is nestled on its own private beach and offers a cabana cafe and a saltwater lagoon. Theatre of the Sea is less than 1 mile away. A private balcony and cable TV are found in each comfortable guest room at the Pelican Cove Resort. Each room is also equipped with a seating area, a small refrigerator and tea- and coffee-making facilities. On-site at the Pelican Cove, guests can enjoy a spacious swimming pool and marina. The property also features a launderette. After a day of fun in the sun, guests can relax at the on-site bar and enjoy a refreshing beer or cocktail. Located steps from the beach, Wild & Lime offers lite lunches and snacks in the afternoon. The Lignumvitae Key Botanical State Park is 10 minutes’ drive away. The San Pedro Underwater Archaeological Preserve State Park is 30 miles away.
Address 84457 Overseas Highway Show on map- Swimming pool
- Ping pong tables
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5 Drop Anchor Resort & Marina
Islamorada
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.
Address 84959 Overseas Highway Show on map- Heated pool
- Water sports facility
- Pets are welcome
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6 Fisher Inn Resort & Marina
Islamorada
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. Laundry facilities 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.
Address 84951 Overseas Highway Show on map- Swimming pool
- Ping pong tables
- Water sports facility
- Pets are welcome
This page contains affiliate links; we may earn a commission, but hotels are listed based on beach proximity and quality, not commission.
Hello! I try my best to keep this guide up to date and I last refreshed it in June 2026. Did I miss a hotel that should be on this list? Send me an email and let me know!