TOP 30 Vacation cottage rentals in Islamorada, Florida

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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.

Clearly Unique Charters is a premier tourist attraction and travel agency located at 81801 Overseas Highway in Islamorada, Florida. Offering a wide range of unique and exciting charter experiences, visitors can explore the stunning waters of the Florida Keys in style. From snorkeling and diving adventures to sunset cruises and fishing trips, Clearly Unique Charters provides unforgettable experiences for all types of travelers. With knowledgeable guides and top-of-the-line equipment, guests can rest assured they are in good hands as they embark on their aquatic journey. Come and discover the beauty of the Florida Keys with Clearly Unique Charters.

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.

The Heart of Morada is a unique institution located at 81906 Overseas Highway in Islamorada, Florida. As a real estate agency, we specialize in helping clients find their dream homes in this beautiful coastal town. Our team of experienced agents is dedicated to providing personalized service and expert guidance throughout the buying or selling process. In addition to our real estate services, we also operate as a travel agency, offering vacation rental properties and booking assistance for those looking to explore all that Islamorada has to offer. Whether you're searching for a permanent residence or a temporary getaway, the Heart of Morada is here to help you find the perfect property to suit your needs.

Little Basin Villas is a premier real estate and travel agency located in the picturesque Islamorada, Florida. Situated at 84 Johnston Road, our institution offers luxurious villas for rent or purchase in this stunning seaside town. Whether you are looking for a vacation rental or a permanent residence, our team of experts is dedicated to helping you find the perfect property to suit your needs. With a focus on personalized service and attention to detail, Little Basin Villas is the ideal choice for those seeking a slice of paradise in the Florida Keys. Contact us today to start your journey towards owning or renting your dream villa in Islamorada.

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.

Buy Florida Keys Property is a finance and real estate agency located at 285 Jasmine Street in Tavernier, Florida. Specializing in Florida Keys short sales, the institution helps both borrowers and lenders navigate the process of selling real estate when the sale proceeds fall short of the loan balance. By avoiding foreclosure, both parties can mitigate financial losses and maintain credit history. Additionally, Buy Florida Keys Property offers services related to foreclosures, providing information on the legal and professional proceedings involved in repossessing a property due to default on a mortgage. The agency also offers services for buying and selling residential properties in Islamorada, Key Largo, and other Florida Keys communities, with a focus on maximizing resale value and choosing a location with economic stability and desirable community amenities. Whether looking to purchase a dream home or vacation property, Buy Florida Keys Property is dedicated to helping clients find the perfect real estate solution in the Florida Keys.

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.

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.

Osprey Bay Villa is a premier real estate agency located at 82754 Overseas Highway in the picturesque town of Islamorada, Florida. Our dedicated team of professionals is committed to helping clients find their dream waterfront property in this stunning coastal community. Whether you are looking for a luxurious vacation home, a cozy beachfront retreat, or a lucrative investment opportunity, Osprey Bay Villa has the expertise and resources to assist you every step of the way. With our extensive knowledge of the local market and personalized approach to customer service, we strive to make the process of buying or selling real estate as smooth and stress-free as possible. Contact us today to start your journey towards owning a piece of paradise in Islamorada.

The Oasis is a unique institution located at 82703 Old Highway in Islamorada, Florida. As a combined real estate and travel agency, we specialize in providing our clients with exceptional service and guidance in all aspects of buying, selling, or renting properties in the beautiful Florida Keys. Our team of experienced professionals is dedicated to helping you find your own personal oasis in this tropical paradise. Whether you are looking for a vacation rental, a permanent residence, or a lucrative investment property, The Oasis is here to make your real estate dreams a reality. Contact us today to start your journey to paradise.

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!

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.

Ocean Sotheby’s International Realty is a prestigious real estate agency located at 81888 Overseas Highway in Islamorada, Florida. We specialize in connecting buyers with truly extraordinary properties in the Florida Keys, including condos, houses, and homes for sale in Sunset Key, Marathon, Key Largo, Key West, and beyond. Our team takes pride in utilizing our extensive experience, resources, and global connections to match unique properties with discerning buyers who appreciate their special qualities. Stay up to date with the latest real estate news and insights from the most desirable neighborhoods in the area by checking out our blog. With our esteemed advertising partners, we are excited to showcase the best of The Florida Keys and help you find your perfect home away from home. Contact us at 305-712-8888 or email us at [email protected] to learn more about our services. Please note that this website is not the official website of Sotheby’s International Realty, Inc., and each office is independently owned and operated. Visit us at our additional locations in Marathon and Key West.

The Maison is a charming and elegant institution located at 80639 Old Highway in Islamorada, Florida. With a prime location in the heart of the Florida Keys, this institution offers a luxurious and tranquil escape for guests looking to relax and unwind. The Maison boasts stunning views of the ocean and is just a short distance from some of the area's best attractions, including world-class fishing, snorkeling, and dining options. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, The Maison provides a welcoming and sophisticated atmosphere for all guests to enjoy.

I Can See CLEAR Kayaking is a unique travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Specializing in clear kayaking adventures, they offer a one-of-a-kind experience where guests can explore the crystal-clear waters of the Florida Keys while paddling through mangrove forests and coral reefs. With knowledgeable guides and top-of-the-line equipment, I Can See CLEAR Kayaking provides a safe and unforgettable journey for nature lovers and adventure seekers alike. Join them for a truly immersive and mesmerizing kayaking experience unlike any other.

Jamie Engel & The Florida Keys Home Team Realtors is a premier real estate agency located at 85996 Overseas Highway in Islamorada, Florida. Specializing in luxury homes in the beautiful Florida Keys, our team of experienced professionals is dedicated to helping clients buy and sell their dream properties. From Key Largo to Key West, we are here to assist with all your real estate needs. With over 17 years of experience in the Florida Keys market, we understand the unique challenges and rewards of buying and selling property in this special area. Our team stays ahead of the curve by keeping up with the latest trends in luxury real estate, utilizing cutting-edge marketing techniques, internet technology, and social media to help clients make informed decisions.

Coastal Realty of the Florida Keys is a premier real estate agency located at 82889 Overseas Highway in Islamorada, Florida. Specializing in properties in the beautiful Florida Keys, this agency offers a wide range of services to help clients buy, sell, or rent their dream homes or vacation properties in this stunning coastal region. With a team of experienced and knowledgeable real estate professionals, Coastal Realty of the Florida Keys is dedicated to providing exceptional service and helping clients find the perfect property to suit their needs and preferences. Whether you are looking for a waterfront home, a luxury condo, or a charming beachfront cottage, this agency has the expertise and resources to make your real estate dreams a reality. Contact Coastal Realty of the Florida Keys today to start your property search in this tropical paradise.

The KeysListings Group at LoKation Real Estate, led by Jim Signor, is a premier real estate institution located at 4 Beach Road, Key Largo, Florida, United States. Established in 2003, KeysListings.com offers the best real estate search for homes and condos in the Florida Keys. The website is easy-to-use and updated every 5 minutes by the official Realtor’s database, the Florida Keys MLS. Visitors can create custom market reports to see active, under contract, and sold properties in their neighborhood and receive market updates on a weekly, bi-monthly, or monthly basis. The institution offers a variety of properties, from gorgeous homes in Key Largo to charming condos in Islamorada. With a focus on customer satisfaction and personalized service, The KeysListings Group at LoKation Real Estate is your go-to source for real estate in the Florida Keys.

Berkshire Hathaway HomeServices Freewheeler Realty is a premier real estate agency located at 85992 Overseas Highway in Islamorada, Florida. With a focus on providing exceptional service and expertise in the local real estate market, our team of experienced agents are dedicated to helping clients find their dream home or investment property in the beautiful Florida Keys. In addition to our real estate services, we also offer travel assistance to those looking to explore the stunning surroundings of Islamorada. Whether you're looking to buy, sell, or rent, Berkshire Hathaway HomeServices Freewheeler Realty is here to help make your real estate dreams a reality.

Allergic to Land Charters is a travel agency located at 84371 Overseas Highway in Islamorada, Florida, United States. Led by Captain Sue DuBon, a seasoned mariner with over 40 years of experience, this agency offers exclusive aquatic adventures in the heart of the Florida Keys. Whether you're interested in snorkeling at vibrant coral reefs, enjoying serene sunset cruises, or exploring eco-friendly tours, Allergic to Land Charters promises unforgettable experiences on the water. With a spacious 22′ Twin Vee Catamaran, Captain Sue provides personalized tours tailored to your interests, ensuring a memorable journey every time. From snorkeling adventures to eco-tours and private excursions, each trip is designed to showcase the natural beauty of the Florida Keys. With over 300 5-star reviews, guests rave about the incredible experiences they've had with Captain Sue and her team. Whether you're a family looking for a fun day out or an enthusiast eager to explore the sea, Allergic to Land Charters offers the perfect adventure for everyone. Book your tour today and discover the wonders of the Florida Keys with Captain Sue DuBon at the helm.

Easy Livin Adventures is a premier travel agency located at 81576 Overseas Highway in Islamorada, Florida. Led by the world famous Captain Augie, a local legend with over two decades of experience in offshore fishing, Easy Livin Adventures offers custom boat tours that are sure to create lasting memories. Captain Augie, known for his sense of humor and larger than life personality, is more than just a tour guide - he is the missing element of fun your vacation needs. He will personally assist and advise you on the best use of your time in Islamorada, ensuring that you have an unforgettable experience.

Welcome to Treasure Key Realty, your premier destination for real estate excellence in Cape Coral, Florida. Located at 1102 Southeast 21st Avenue, our agency is dedicated to helping you find your dream property or sell your home for top dollar. Led by Tara Brommer, a seasoned REALTOR® and Broker-Owner, our team is committed to providing clear, concise, and no-nonsense communication to ensure a seamless real estate experience for our clients. At Treasure Key Realty, we specialize in showcasing extraordinary properties in our featured areas, including the stunning Florida Keys. Whether you're dreaming of constructing a luxury residence on expansive acreage or seeking a charming home in the heart of Cape Coral, we have the expertise and resources to make your real estate goals a reality.