TOP 30 Relaxing vacation in Islamorada, Florida

Island Bay Resort is a tropical oasis located at 92530 Overseas Highway in Tavernier, Florida, United States. Our beachfront location on the Florida Bay offers stunning sunsets and a relaxing atmosphere surrounded by palm trees and flowering plants. Whether you're looking to unwind and escape everyday stress or seeking adventure in the Florida Keys, our resort has something for everyone. Centrally located between Key Largo and Islamorada, just two hours from Key West or the Miami/Ft. Lauderdale area, Island Bay Resort is the perfect destination for your next vacation. Enjoy our tiki huts, hammocks, swimming, snorkeling, boating, and sunbathing on our private beach.

Islander Resort is a luxurious lodging facility located at 82100 Overseas Highway in the beautiful town of Islamorada, Florida. Situated in the heart of the Florida Keys, this resort offers guests a serene and picturesque retreat with stunning ocean views and pristine beaches. The resort features spacious and well-appointed rooms, a range of amenities including a pool, spa, and on-site dining options. Perfect for a romantic getaway, family vacation, or corporate retreat, Islander Resort provides a peaceful and relaxing atmosphere for guests to unwind and enjoy the tropical paradise of the Florida Keys.

Located at 83409 Overseas Highway in Islamorada, Florida, the Chesapeake Beach Resort is a stunning seaside lodging destination that exceeds all expectations. As the Sport Fishing Capital of the World, Islamorada offers a relaxed atmosphere and year-round activities for guests to enjoy. Each room at the resort features comfortable beds and a tranquil ambiance, with the option to choose a Garden View room with a private balcony or upgrade to a suite or villa for added luxury. Surrounded by crystal blue waters and white sandy beaches, the resort offers a picturesque setting for a relaxing and breathtaking vacation.

The Key Lantern Motel is a charming lodging establishment located at 82150 Overseas Highway in Islamorada, Florida. Situated in the heart of the Florida Keys, this motel offers cozy and comfortable accommodations for travelers looking to relax and unwind. With its convenient location near the beach and various local attractions, guests can enjoy a peaceful stay while exploring the beautiful surroundings. The Key Lantern Motel provides a welcoming atmosphere and excellent hospitality, making it a perfect choice for a memorable vacation in the sunshine state.

The Caribbean Resort, located at 117 Carroll Street in Islamorada, Florida, is a charming lodging option that offers a taste of the Caribbean right in the heart of the United States. With its tropical-inspired decor, lush gardens, and stunning ocean views, this resort is the perfect escape for those looking to relax and unwind in a beautiful setting. Whether you're lounging by the pool, enjoying a cocktail at the beachside bar, or exploring the nearby attractions, The Caribbean Resort provides a tranquil and luxurious retreat for guests seeking a slice of paradise.

Welcome to Best of Both Worlds Resort, a luxurious lodging destination located in the heart of Islamorada, Florida. Situated along the picturesque Overseas Highway, our resort offers the perfect blend of relaxation and adventure, providing guests with the best of both worlds. Our resort features spacious and beautifully appointed rooms, each designed to provide a comfortable and inviting atmosphere for our guests. Whether you're looking to unwind by the pool, indulge in a spa treatment, or explore the natural beauty of the Florida Keys, Best of Both Worlds Resort has something for everyone.

Coral Bay Resort, located at 75690 Overseas Highway in Islamorada, Florida, offers a relaxing and picturesque lodging experience. Guests can unwind in the fresh water heated pool after a day of exploring the waters. The resort grounds are beautifully landscaped with hibiscus and native Keys Palms, leading to a sandy beach that gently slopes into the crystal clear Gulf of Mexico. The sunsets are always stunning, and the waters beyond the dock are illuminated at night for guests to enjoy the marine life. Boaters are welcome to bring their boats, with no additional charges for boat dock and private ramp use, as well as ample trailer storage on site. Guests can relax under the illuminated tiki and enjoy the peaceful bay views in the evening.

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.

Located at 80401 Old Highway in Islamorada, Florida, the Pines and Palms Resort is a charming lodging institution that offers boutique-style accommodations right on the Atlantic Ocean. The resort is designed as a peaceful tropical village, with oceanfront cottages and suites for an authentic Florida Keys experience. Guests can enjoy daily natural spectacles, fiery sunrises, and a laid-back lifestyle that embodies the essence of Keys life. The resort boasts an oceanfront climate-controlled pool for relaxation, as well as seasonal yoga classes for rejuvenation. With personalized service and genuine hospitality, guests are welcomed as family at Pines and Palms Resort. Visitors can take advantage of complimentary kayaks, paddle boards, and bike rentals, as well as sunset sails and private fishing charters for added adventure.

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.

The Moorings Village is a charming lodging institution located at 123 Beach Road in Islamorada, Florida, United States. Nestled in a picturesque seaside setting, this luxurious retreat offers guests a tranquil and rejuvenating escape from the hustle and bustle of everyday life. With its beautifully appointed accommodations, lush tropical gardens, and pristine white sandy beaches, The Moorings Village provides the perfect backdrop for a relaxing vacation or romantic getaway. Whether you are seeking a peaceful retreat or an adventurous beach vacation, The Moorings Village offers a unique and unforgettable experience for all who visit.

Matecumbe Resort is a lodging institution located at 76261 Overseas Highway in Islamorada, Florida, United States. Situated on an oceanfront setting, our resort offers 32 recently remodeled units with fully equipped in-suite kitchens. Each unit includes a microwave, stove, refrigerator, pots & pans, toaster, and coffee maker. Additionally, all rooms feature a seating area with a sleeper sofa and an outdoor porch. Relax in our welcoming accommodations that provide all the essentials of home and more. Choose from a variety of room options, all equipped with full kitchens. Our large one-bedroom 1st floor suites offer beautiful views of the grounds and ocean.

Sundance Watersports is a premier travel agency located at 77522 Overseas Highway in Islamorada, Florida. We specialize in providing unforgettable water-based experiences for our clients, including snorkeling tours, paddleboarding adventures, and jet ski rentals. Our knowledgeable staff are dedicated to helping you create the perfect vacation itinerary, whether you're looking to relax on the beach or explore the crystal-clear waters of the Florida Keys. Come visit us and let us help you make the most of your time in this beautiful coastal paradise.

Founders Park Pool is a popular community swimming pool located at 87000 Overseas Highway in Islamorada, Florida. This family-friendly facility offers a refreshing escape from the Florida heat with its crystal-clear waters and spacious deck area for lounging in the sun. The pool is surrounded by lush tropical landscaping, creating a serene and relaxing atmosphere for visitors of all ages. Whether you're looking to swim laps, splash around with the kids, or simply unwind by the water, Founders Park Pool is the perfect destination for a day of fun in the sun. With its convenient location and well-maintained facilities, this pool is a must-visit for locals and tourists alike.

Breezy Palms Resort is a charming lodging destination located in the beautiful Islamorada, Florida. Situated at 80015 U.S. 1, this tropical oasis offers guests a relaxing and unforgettable experience in the heart of the Florida Keys. With cozy accommodations, stunning ocean views, and a range of amenities including a pool, beach access, and on-site dining options, Breezy Palms Resort is the perfect choice for those looking to unwind and soak up the sun in paradise. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, this resort has everything you need for a memorable stay. Book your stay at Breezy Palms Resort and escape to a slice of paradise in Islamorada.

Topsiders Resort is a charming lodging establishment located at 75500 Overseas Highway in the picturesque town of Islamorada, Florida. This tropical oasis offers guests a relaxing and comfortable stay in the heart of the Florida Keys. The resort features spacious and well-appointed rooms, a sparkling swimming pool, and stunning views of the surrounding landscape. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Topsiders Resort is the perfect destination for your next trip to paradise. With its convenient location and top-notch amenities, this resort is sure to provide a memorable and enjoyable experience for all guests.

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.

Anglers Reef 140 Rental is a real estate and travel agency located at 140 Anglers Way in Islamorada, Florida, United States. This stunning property offers 3 bedrooms, 2.5 baths, and breathtaking oceanfront views. Guests can enjoy huge decks, optional boat slips, and a gated community for added security. Located in the heart of Islamorada, guests have access to a variety of dining, activities, and shopping options. Whether you're looking to relax on the beach or explore the vibrant local culture, this property has something for everyone.

Ocean Oasis at Ocean Pointe is a luxurious vacation destination located in Tavernier, Florida. This stunning institution offers a range of amenities including a pool, Jacuzzi, tennis and pickleball courts, a private beach, and a marina. Centrally located between Islamorada and Key Largo, guests can easily explore the surrounding areas and enjoy all that the Florida Keys have to offer. Whether you're looking for a relaxing beach getaway or an active vacation filled with water sports and outdoor activities, Ocean Oasis at Ocean Pointe has something for everyone. Contact our real estate and travel agency at 500 Burton Drive to book your dream vacation today.

Rental Boat Co is a premier boat rental company located at 79851 Overseas Highway in Islamorada, Florida. We offer a wide selection of high-quality boats for rent, perfect for exploring the beautiful waters of the Florida Keys. Whether you're looking for a relaxing day of fishing, a thrilling ride on a speedboat, or a leisurely cruise to enjoy the sunset, Rental Boat Co has the perfect vessel for you. Our experienced and friendly staff are dedicated to providing top-notch customer service and ensuring you have a safe and enjoyable boating experience. Come visit us at Rental Boat Co and start your adventure on the water today!

The Beach House at Tarpon Point is a luxurious oceanfront home located at 77521 Overseas Highway in Islamorada, Florida. This stunning property offers amazing ocean views, a sandy beach, pool, and an observation pier perfect for watching sunrises and sunsets. As a real estate and travel agency, The Beach House provides top-notch amenities and furnishings to ensure a relaxing and memorable vacation experience for all guests. Whether you're looking for a peaceful retreat or a fun-filled getaway, The Beach House at Tarpon Point is the perfect destination for your next trip to the beautiful Florida Keys.

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.

KeysVacationHouse.com is a premier real estate and travel agency located at 88005 Overseas Highway in Islamorada, Florida. Specializing in luxurious vacation rentals in the beautiful Florida Keys, our agency offers a wide selection of stunning properties for visitors to choose from. Whether you are looking for a cozy beachfront cottage or a spacious waterfront villa, we have the perfect vacation house to suit your needs. Our team of experienced agents is dedicated to providing exceptional customer service and helping you find the ideal accommodation for your dream getaway. Book your next vacation with KeysVacationHouse.com and experience the ultimate in comfort and relaxation in the tropical paradise of the Florida Keys.

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.

Venetian Tropics is a luxurious lodging and real estate agency located at 106 San Remo Drive in the stunning Islamorada, Florida. Nestled in the heart of the Florida Keys, this institution offers a unique blend of tropical charm and Venetian elegance. Whether you are looking for a relaxing vacation rental or seeking to invest in a piece of paradise, Venetian Tropics has a team of expert agents ready to assist you. With a prime location near the turquoise waters of the Atlantic Ocean, guests and clients alike can enjoy the ultimate tropical getaway experience. Book your stay or find your dream property with Venetian Tropics today!

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.

Pineapple Beach is a premier real estate and travel agency located at 130 Aregood Lane in the beautiful coastal town of Islamorada, Florida. Our team of experienced professionals is dedicated to helping clients find their dream beachfront property or plan the perfect tropical getaway. With a focus on personalized service and attention to detail, Pineapple Beach is committed to making your real estate or travel experience seamless and unforgettable. Contact us today to start your journey to paradise.

KeyZ Charters is a premier tourist attraction and travel agency located at 77522 Overseas Highway in Islamorada, Florida. Offering a variety of private boat tours and charters, KeyZ Charters is the perfect choice for exploring the Florida Keys, Everglades National Park, and South Florida. From snorkeling adventures to sunset cruises, bird-watching excursions, and eco-tours, KeyZ Charters provides exhilarating experiences for the whole family. Located in South Florida, KeyZ Charters can take you up close to popular landmarks such as Indian Key, Lignumvitae Key, Alligator Reef lighthouse, and Everglades National Park. Our experienced guides will ensure you have a memorable experience while observing local wildlife and enjoying the natural beauty of the area.