The 30 Best Waterfront resorts keys in Islamorada, Florida

Located at 84001 Overseas Highway in Islamorada, Florida, the Postcard Inn Beach Resort and Marina offers a unique and authentic Keys experience. As the "Sportfishing Capital of the World," guests can bring their own boat or book an excursion to explore the waters surrounding this beautiful resort. With the merging of two Islamorada resorts into one destination, the Postcard Inn Resort & Marina is set to become the heartbeat of the Islamorada Resort Collection in 2024. Offering island-chic guestrooms, exciting culinary experiences, a lively marina, a stunning beachfront, and a variety of activities, guests can seamlessly transition between adventure and relaxation from sunrise to sunset.

Drop Anchor Resort & Marina is a charming lodging establishment located at 84959 Overseas Highway in the beautiful Islamorada, Florida. This waterfront resort offers a serene and relaxing escape for guests looking to unwind and enjoy the stunning views of the Florida Keys. With comfortable accommodations, a marina for boat enthusiasts, and a range of amenities including a pool and beach access, Drop Anchor Resort & Marina is the perfect destination for a memorable vacation in the heart of the Keys.

KeysCaribbean Resorts is a premier lodging institution located at 97501 Overseas Highway in Key Largo, Florida, United States. Our team of professional agents is available 24 hours a day to ensure a stress-free and exceptional vacation experience for our guests. Choose from our select rentals at premier Upper & Middle Keys resort communities, where you'll have exclusive access to top-notch amenities such as private swimming pools, boat dockage, Jacuzzi tubs, and more. Whether you're planning a family reunion or a getaway with friends, we can accommodate your needs with our range of rental options.

Ragged Edge Resort and Marina is a charming lodging establishment located at 243 Treasure Harbor Drive in the picturesque town of Islamorada, Florida. Situated right on the waterfront, this resort offers guests stunning views of the marina and the crystal clear waters of the Florida Keys. The resort features comfortable accommodations, a variety of amenities, and easy access to all the outdoor activities and attractions the area has to offer. Whether you're looking to relax by the pool, go fishing, or explore the local shops and restaurants, Ragged Edge Resort and Marina is the perfect place to unwind and enjoy a memorable vacation in paradise.

Hadley Resort Marina is a stunning oceanfront lodging establishment located at 82749 Overseas Highway in Islamorada, Florida. Situated in the heart of the Florida Keys, our resort offers easy access to all of the popular activities in the area. Our guest rooms are beautifully designed and equipped with modern amenities such as HDTVs and free WiFi to ensure a comfortable stay. Whether you choose a spacious suite or a cozy standard room, we have accommodations to fit every budget.

Located at 81200 Overseas Highway in Islamorada, Florida, the Kon-Tiki Resort is a charming lodging institution that offers a unique and unforgettable vacation experience. Nestled in the heart of Islamorada, our resort boasts fully-equipped villa accommodations and an unbeatable location on the Florida Bay, making it the perfect destination for those seeking a relaxing getaway. With 23 unit accommodations to choose from, each with its own unique flair, guests can enjoy a range of options including standard rooms, spacious efficiency apartments, and villas complete with a kitchen, living room, and dining area. Our accommodations are designed to provide ultimate comfort and style for our guests.

Coconut Cove Resort & Marina is a charming lodging establishment located at 84801 Old Highway in the picturesque town of Islamorada, Florida. This waterfront resort offers guests a tranquil and tropical escape, with cozy accommodations and stunning views of the marina. Whether you're looking to relax by the pool, explore the nearby beaches, or enjoy water activities like fishing and snorkeling, Coconut Cove Resort & Marina has something for everyone. With its convenient location and welcoming atmosphere, this resort is the perfect destination for a relaxing getaway in the Florida Keys.

Islamorada Ocean Oasis is a premier real estate and travel agency located at 75831 Overseas Highway in Islamorada, Florida. Our team of dedicated professionals specialize in providing clients with luxurious oceanfront properties and unforgettable travel experiences in the stunning Florida Keys. Whether you are looking to invest in a beachfront paradise or plan your dream vacation, Islamorada Ocean Oasis is here to make your dreams a reality. Contact us today to start your journey to paradise.

Keys Ocean House is a charming lodging establishment located at 76311 Overseas Highway in the picturesque town of Islamorada, Florida. This quaint and cozy inn offers guests a peaceful and relaxing stay right by the ocean. The rooms are tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning views of the ocean from their rooms or take a leisurely stroll along the beach. The friendly staff is always ready to assist with any requests or recommendations for activities in the area. Whether you're looking for a romantic getaway or a family vacation, Keys Ocean House is the perfect choice for a memorable stay in the Florida Keys.

Florida Keys Vacation Rentals Inc. is a premier real estate and travel agency located at 85996 Overseas Highway in Islamorada, Florida. Specializing in vacation rentals in the beautiful Florida Keys, our team is dedicated to helping clients find the perfect property for their getaway. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront villa, we have a wide range of options to choose from. Let us help you make your dream vacation a reality in this tropical paradise. Contact us today to start planning your unforgettable trip to the Florida Keys.

Islamorada Vacation Rental is a premier lodging option located at 101 Leoni Drive in Islamorada, Florida. As a combination of a real estate agency and travel agency, we specialize in providing top-quality vacation rentals for visitors looking to experience the beauty and charm of the Florida Keys. Our properties offer a range of amenities and locations, ensuring that guests have a comfortable and memorable stay. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious waterfront home, Islamorada Vacation Rental has the perfect option for you. Book with us today and start planning your dream vacation in paradise.

Casa Rio Islamorada is a charming lodging institution located at 121 Sapodilla Drive in Islamorada, Florida. Nestled in the heart of the Florida Keys, this cozy retreat offers a peaceful and serene atmosphere for guests to relax and unwind. With comfortable accommodations and a welcoming staff, Casa Rio Islamorada is the perfect place to escape the hustle and bustle of everyday life. Whether you're looking for a romantic getaway or a family vacation, this hidden gem is sure to provide a memorable experience. Explore the beautiful surroundings, soak up the sun on the nearby beaches, or simply enjoy a leisurely stroll along the waterfront. Come and experience the laid-back charm of Casa Rio Islamorada for yourself.

Indian Key Historic State Park is a unique and historic institution located on an offshore island in Islamorada, Florida, United States. Accessible only by kayak launch, this park offers a glimpse into the past as it was once the first county seat for Dade County in 1836. The island was a hub for salvaging cargo from shipwrecks in the Florida Keys, making it a lucrative business at the time. Today, visitors can enjoy swimming, sunbathing, and hiking on the island. Kayak rentals are available from local charter companies for those looking to explore the area by water. Please note that as of Sept. 29, 2021, the boat ramp at Indian Key Fill is closed due to storm damage, and the observation tower is also closed. Park fees can be paid in cash at the iron ranger near the kayak launch or in advance using the "Pay Online Single-Use Day Pass" link. Visit Indian Key Historic State Park for a unique and educational experience in the beautiful Florida Keys.

Lazy Days is an award-winning restaurant located in Islamorada, Florida, offering the freshest seafood in town. Enjoy oceanfront dining with exquisite Keys-style dishes such as seafood pastas, vegetarian options, sandwiches, certified Angus steaks, and chicken at reasonable prices. The restaurant has been voted "Best Restaurant Overall", "Best Waterfront Dining", "Best Seafood Restaurant", "Best Lunch", and "Best Wait Staff" in the Upper Keys People's Choice Awards. With spectacular views from tables nestled in the sand, an outside upstairs patio overlooking the Atlantic, and a cozy Keys-style atmosphere indoors, Lazy Days offers a unique dining experience. The full-service bar serves a variety of drinks, including craft beers, wines, and specialty cocktails. Don't forget to visit the Lazy Days Seafood Market for the freshest seafood in town and stop by the gift shop for custom t-shirts, hats, and more.

Nestled in the picturesque town of Islamorada, Florida, Treasure Harbor is a charming lodging institution located at 200 Treasure Harbor Drive. Offering a tranquil and relaxing atmosphere, this hidden gem is the perfect destination for those seeking a peaceful getaway in the heart of the Florida Keys. With comfortable accommodations, stunning views of the harbor, and a range of amenities, including a pool and on-site restaurant, Treasure Harbor provides guests with a truly unforgettable experience. Whether you're looking to unwind by the water or explore the local attractions, Treasure Harbor is the ideal choice for your next vacation.

Anglers Reef Villas is a luxurious waterfront lodging option located at 110 Anglers Way in Islamorada, Florida. As a combination of a lodging, real estate, and travel agency, Anglers Reef Villas offers guests the opportunity to experience the ultimate vacation in paradise. With stunning views of the ocean, top-notch amenities, and a prime location near popular attractions, Anglers Reef Villas is the perfect choice for those seeking a memorable stay in the Florida Keys. Whether you're looking to relax on the beach, explore the local area, or invest in a vacation home, Anglers Reef Villas has everything you need for a truly unforgettable experience.

Islander Bayside Villas is a charming lodging institution situated at 81450 Overseas Highway in the picturesque town of Islamorada, Florida. Nestled along the beautiful bayside, this tranquil retreat offers guests a peaceful and relaxing atmosphere with stunning views of the water. The villas are tastefully decorated and equipped with modern amenities to ensure a comfortable stay for visitors. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, Islander Bayside Villas provides the perfect escape in the heart of the Florida Keys.

Bud N' Mary's Marina is a charming lodging institution located at 79851 Overseas Highway in Islamorada, Florida, United States. Situated right on the water, this marina offers guests the opportunity to stay in comfortable accommodations while enjoying easy access to fishing charters, boat rentals, and water sports activities. With its picturesque surroundings and convenient location, Bud N' Mary's Marina is the perfect destination for those looking to experience the beauty and excitement of the Florida Keys.

Wet Net Villas is a charming waterfront resort located at 81101 Overseas Highway in Islamorada, Florida. Offering luxurious accommodations with stunning views of the ocean, this institution is the perfect destination for a relaxing getaway. Guests can enjoy a range of amenities including a private beach, swimming pool, and on-site dining options. Whether you're looking to unwind by the water or explore the nearby attractions, Wet Net Villas provides the ideal setting for a memorable vacation in the beautiful Florida Keys.

SuCasa Vacation Rentals is a charming lodging institution located at 77360 Overseas Highway in the picturesque town of Islamorada, Florida. Offering a variety of vacation rental options, SuCasa provides guests with a home away from home experience in the heart of the Florida Keys. Whether you are looking for a cozy cottage by the beach or a luxurious waterfront villa, SuCasa has the perfect accommodation for your vacation needs. With top-notch amenities, personalized service, and a convenient location near local attractions and activities, SuCasa Vacation Rentals is the ideal choice for a memorable stay in Islamorada.

Welcome to The "Nest" Villa, located at 82236 Overseas Highway in Islamorada, Florida. Our villa is the perfect home away from home for your next Florida Keys vacation. Situated in a central part of Islamorada, our property is close to local attractions, shops, bars, and restaurants, many of which are within walking distance. Our villa is one of only seven units on the property, nestled on a shaded one-acre tropical hammock that stretches from the highway down to the beautiful shores of Florida Bay. The villa is secluded and private, with stunning views of the water and spectacular sunsets.

Beacon Reef Condominiums is a luxurious waterfront property located at 83201 Old Highway in Islamorada, Florida. These stunning condominiums offer breathtaking views of the ocean and are surrounded by lush tropical landscaping. Residents can enjoy resort-style amenities such as a pool, fitness center, and private beach access. The spacious units feature modern finishes and open floor plans, perfect for entertaining guests or relaxing in style. With its prime location in the heart of the Florida Keys, Beacon Reef Condominiums is the perfect place to call home for those seeking a peaceful and upscale coastal lifestyle.

Coral Harbour Condo Association is a vibrant community located at 88181 Old Highway in Islamorada, Florida. Our association is dedicated to creating a welcoming and inclusive environment for all residents. Our beautiful condos offer stunning views of the surrounding area and access to a range of amenities, including a pool, fitness center, and tennis courts. With a strong sense of community and a commitment to maintaining our properties to the highest standards, Coral Harbour Condo Association is the perfect place to call home in the Florida Keys.

Executive Bay Club is a premier institution located at 87200 Overseas Highway in Islamorada, Florida. It offers a luxurious and exclusive experience for its members, featuring top-notch amenities and services. With stunning views of the surrounding area and access to a range of recreational activities, Executive Bay Club is the perfect destination for those seeking a high-end lifestyle in the heart of the Florida Keys. Whether you're looking to relax by the pool, enjoy a game of tennis, or indulge in gourmet dining, this institution has everything you need for a truly unforgettable experience.

Blackbeard Private Charters is a premier travel agency located at 85920 Overseas Highway in Islamorada, Florida. Specializing in private custom boat charters, Blackbeard Charters offers a unique opportunity to experience the Florida Keys like a local. Whether you're looking to relax at the Islamorada Sandbar or explore the vibrant reefs in the upper Keys, our experienced team is dedicated to providing you with the trip of a lifetime. Swim among tropical fish, soak up the sun, and create unforgettable memories with Blackbeard Private Charters.