Luxury resort holidays in Islamorada, Florida

Sands of Islamorada Hotel & Resort is a luxurious lodging destination located at 80051 Overseas Highway in Islamorada, Florida. Offering a perfect blend of tropical charm and modern amenities, this resort is the ideal retreat for those seeking a relaxing getaway in the beautiful Florida Keys. Guests can enjoy stunning ocean views, pristine beaches, and top-notch service during their stay. Whether you're looking to relax by the pool, explore the nearby attractions, or indulge in delicious dining options, Sands of Islamorada Hotel & Resort has everything you need for a memorable vacation experience.

Located at 80241 Overseas Highway in Islamorada, Florida, La Siesta Resort & Villas offers a tropical island style getaway with spacious guest rooms, beachside cottages, and private vacation homes. Experience authentic Keys life with island-inspired flavors and legendary cocktails while enjoying stunning sea views. The resort features lush private beaches, pools with ocean views, and fishing charters for the catch of your dreams. Accommodations include suites, cottages, and villas with idyllic Islamorada views and unique resort amenities. Special offers include discounts for Florida and Georgia residents, military personnel, and tax season rewards. Enjoy dining at Wild & Lime and nearby restaurants, as well as unforgettable experiences for special occasions. Plan your dream destination wedding or arrive at the Florida Keys marina for a seamless vacation experience. Explore all that La Siesta Resort & Villas has to offer and make memories to last a lifetime.

Experience the ultimate Florida Keys vacation at Angler's Reef Resort Select Rentals by KeysCaribbean. Located in the picturesque town of Islamorada, this stunning resort offers 52 cottages inspired by Caribbean fishing villages, complete with deep-water boat docks and luxurious amenities. Enjoy two-bedroom, two and a half bath rentals with spacious decks and full kitchens, perfect for a relaxing getaway. With easy access to Alligator Reef and the only living coral barrier reef in the Continental United States, anglers will delight in the abundant marine life in the area. Take advantage of special offers and discounts to make your stay even more memorable. Whether you're planning a last-minute getaway or booking in advance, Angler's Reef Resort has the perfect package for you. Relax by the oceanfront swimming pool or private beach, or explore the vibrant marine life just offshore. With Snake Creek Marina nearby, boating enthusiasts can easily access the Atlantic Ocean for deep-sea adventures. Discover the charm of Islamorada and experience the best of the Florida Keys at Angler's Reef Resort. Book your stay today and immerse yourself in the beauty of this tropical paradise.

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.

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.

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.

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.

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.

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.

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.

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!

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.