The 30 Best Florida luxury rentals in Islamorada, Florida

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.

Freewheeler Vacations is a premier real estate and travel agency located in the beautiful coastal town of Islamorada, Florida. Our team of experienced professionals specialize in helping clients find their dream vacation rental or investment property in this stunning tropical paradise. Whether you're looking for a luxurious beachfront villa or a cozy cottage by the water, we have the expertise to make your vacation dreams a reality. Come visit us at 85992 Overseas Highway and let us help you plan the perfect getaway in the Florida Keys.

Latitude Key Vacations is a premier real estate and travel agency located at 3324 Northeast 32nd Street in Fort Lauderdale, Florida, United States. Specializing in curating vacation properties across three collections - Villas, Residences, and Homes - our properties are situated in high-end, quiet neighborhoods in Fort Lauderdale, Pompano Beach, Lauderdale-by-the-Sea, West Palm Beach, Islamorada (The Keys), Hollywood, and Delray Beach. We pride ourselves on offering meticulously equipped accommodations with lavish linens, opulent towels, natural Pure Fiji toiletries, and convenient starter kits. Our commitment to providing a perfect vacation experience includes round-the-clock support and additional services to elevate your stay. Our expertly designed villas boast high-end amenities and waterfront tranquility, providing the ultimate vacation experience. Floridian style residences feature heated pools in backyards with lounge areas, ideal for a serene getaway. Explore the unique charm of Fort Lauderdale, Hollywood, Lauderdale-By-The-Sea, Pompano Beach, West Palm Beach, and Delray Beach through our range of properties located in these vibrant destinations. Whether you prefer a beachfront property or a city center location, we offer a variety of accommodations to suit your needs.

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.

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.

Tea Table Key Island Estate & Wedding Venue is a luxurious and exclusive private island located in Islamorada, Florida. This stunning Caribbean island is accessible by car and offers unparalleled privacy and beauty. The estate features a 5 bedroom main home, separate living quarters, pool, cabana, dockage, helipad, and tennis court. With floor to ceiling windows and wraparound views, the main home provides a truly immersive experience of the surrounding waters and Alligator Reef Light. The expansive master bedroom on the second floor offers breathtaking sunrises and sunsets from every window and patio. This vacation rental is available for $25,000 - $35,000 weekly, with additional fees for holiday weddings and events. To inquire about booking this extraordinary property, contact (305) 664-3333 or email rentals@islandvilla.com.

Island Adventures is a premier travel agency located at 80500 Overseas Highway in Islamorada, Florida. Specializing in creating unforgettable island getaways, our dedicated team of travel experts can help you plan the perfect vacation to tropical destinations around the world. From luxurious beach resorts to thrilling outdoor excursions, Island Adventures offers a wide range of travel options to suit every traveler's preferences. Let us help you turn your dream island getaway into a reality. Book your next adventure with Island Adventures today!

Easy Keys Charters is a premier private charter service located at 80460 Overseas Highway in Islamorada, Florida. As a top travel agency in the area, we specialize in providing unforgettable experiences on the water. Whether you're looking to go fishing, snorkeling, or simply enjoy a relaxing cruise, our experienced team is here to make your trip a memorable one. Book your next adventure with Easy Keys Charters online or give us a call at (305) 509-3075.

Tan Line Charters is a premier travel agency located at 80460 Overseas Highway in Islamorada, Florida. Specializing in luxury yacht charters, Tan Line Charters offers unforgettable experiences on the crystal-clear waters of the Florida Keys. Whether you're looking for a relaxing day on the water or an adventurous deep-sea fishing excursion, our experienced team will create a customized itinerary to suit your every need. Embark on a journey with Tan Line Charters and discover the beauty of the ocean in style and comfort.

Lightly Salted Charters is a top-quality travel agency located at 80500 Overseas Highway in Islamorada, Florida. Embark on the Ultimate Florida Keys Adventure on our 2015, 26′ Twin Vee with Captain Zander. From Flats to Offshore Fishing, Snorkeling Tours, Sandbar Getaways & Mesmerizing Sunsets, we offer fully custom trips for every angler. Experience the magic of sunset tours, snorkeling, sandbar & sunset tours, and fishing all in one unforgettable journey. Our all-inclusive Islamorada sandbar tour takes you to the world-famous Islamorada Sandbar for an unforgettable vacation. With our expert snorkel guide, enjoy 5-star private snorkeling tours through the fabulous coral reefs. Our boat can accommodate a maximum of six passengers, but we can add more boats to accommodate larger groups. Book a trip with Lightly Salted Charters and create memories that will last a lifetime. Schedule your private charter boat tour with us today at (305)205-3500.

Easy Livin Charter is a renowned travel agency located at 81576 Overseas Highway in Islamorada, Florida, United States. Led by the world famous Captain Augie, who is a local legend in the community, Easy Livin Charter offers custom boat tours that are sure to create lasting memories for all who embark on them. With over two decades of experience in offshore fishing and a deep knowledge of the area, Captain Augie is more than just a tour guide - he is a source of fun and entertainment for all guests. His sense of humor and larger than life personality are guaranteed to put a smile on your face as you explore the beautiful waters of Islamorada.

Capt. Jack Backus is a reputable travel agency located at 79901 Overseas Highway in the beautiful town of Islamorada, Florida. Specializing in providing top-notch travel experiences and adventures, Capt. Jack Backus offers a wide range of services including booking flights, hotels, cruises, and tours. With a team of experienced and knowledgeable travel experts, this agency is dedicated to helping clients plan unforgettable vacations and create lasting memories. Whether you're looking for a relaxing beach getaway, an exciting outdoor adventure, or a romantic escape, Capt. Jack Backus has you covered. Contact them today to start planning your dream vacation!

Solfinis Sunset Cruise is a premier travel agency located at 84001 Overseas Highway in Islamorada, Florida. Specializing in unforgettable sunset cruises, we offer a luxurious and relaxing experience on the beautiful waters of the Florida Keys. Our expert staff will ensure that every detail of your cruise is perfect, from the stunning views to the delicious cocktails served on board. Whether you're looking for a romantic evening with your loved one or a fun outing with friends, Solfinis Sunset Cruise is the perfect choice for a memorable experience on the water. Book your cruise today and prepare for an unforgettable journey into the sunset.

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.

Overseas Leisure Group, located at 814 Ponce de Leon in Miami, Florida, is a luxury travel agency with a passion for creating unique and authentic experiences in the Americas and beyond. They specialize in providing exclusive rental properties such as Casa Los Cayos in Islamorada, Florida and the Rio Negro Queen luxury floating hotel in Manaus, Brazil. Overseas Leisure Group takes pride in ensuring that each traveler has a personalized and unforgettable experience, working with local insiders to connect visitors to the true spirit of their destination. With a reputation for exceptional service and attention to detail, Overseas Leisure Group is a trusted partner for travelers seeking extraordinary and memorable adventures.

True Island Adventures is a premier travel agency located in the heart of Islamorada, Florida. Our team of experienced professionals is dedicated to providing unforgettable experiences for those seeking the ultimate island adventure. Whether you're looking to explore the crystal-clear waters of the Florida Keys, encounter exotic wildlife, or simply relax on pristine beaches, True Island Adventures has you covered. With a wide range of customizable tour packages and expert guides, we ensure that every trip is tailored to your individual preferences and interests. Come and discover the true beauty of the islands with True Island Adventures.

Bluewater Adventure is a premier institution located at 81576 Overseas Highway in Islamorada, Florida, United States. Specializing in boat rentals, sandbar trips, and sunset tours, Bluewater Adventure offers a luxurious and pampering experience for all guests. Step aboard your chartered vessel and enjoy the freedom to bring your favorite food and beverages on board. With amenities such as a bar area and Bluetooth connectivity, you can set the soundtrack for your adventure and relax while cruising along the azure waters. Whether you prefer lively beats or tranquil melodies, the music is yours to control, creating the perfect ambiance for your voyage. Visit Bluewater Adventure at Shelter Cove Marina in Hilton Head Island, SC for an unforgettable experience on the water.

Purple Isle Charters is a premier travel agency located in the beautiful town of Islamorada, Florida. Situated at 85920 Overseas Highway, this institution specializes in providing unforgettable charter experiences for visitors looking to explore the stunning waters of the Florida Keys. With a fleet of top-of-the-line boats and experienced captains, Purple Isle Charters offers a wide range of customizable charter options, including fishing trips, snorkeling excursions, sunset cruises, and more. Whether you're a seasoned angler or a first-time visitor, Purple Isle Charters is dedicated to providing exceptional service and creating lasting memories for all who embark on their adventures. Book your charter today and discover the magic of the Florida Keys with Purple Isle Charters.

Caribbean Catering, located at 80925 Overseas Highway in Islamorada, Florida, offers a wide range of affordable Florida Keys wedding planning and catering services. Specializing in Islamorada weddings and Keys sunset beach weddings, we strive to personalize every detail to make your special event truly unique. Our professional and friendly team works together to ensure that your guests are taken care of and that the food is excellent. From discussing decor and cake options to providing stress-free planning, we are dedicated to making your wedding day a dream come true. With a one-stop shop approach, we cover all the details from planning to clean-up, making us the perfect choice for your Islamorada wedding. Contact us today to see how we can make your event unforgettable.

Welcome to 55 Concierge Services LLC, your dedicated partner in real estate and travel, located in the beautiful community of Punta Gorda, Florida. Nestled at 453 Islamorada Boulevard, our agency specializes in providing exceptional services tailored for the 55 community. Whether you are looking to find your dream home or embark on your next travel adventure, our team of experienced professionals is here to assist you every step of the way. As a premier real estate agency, we offer personalized assistance in buying, selling, and managing properties, ensuring a seamless and stress-free experience. Our deep understanding of the local market and commitment to client satisfaction set us apart, making us the go-to choice for real estate needs in Punta Gorda and beyond.

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.