TOP 30 Luxury beach holidays in Islamorada, Florida

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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.

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.

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.

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.

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.

Anglers Reef Vacation Rental is a premier real estate and travel agency located at 109 Anglers Way in Islamorada, Florida. Our vacation rentals offer luxurious accommodations in a picturesque setting, perfect for those looking to escape and unwind in the beautiful Florida Keys. From cozy beachfront cottages to spacious waterfront villas, we have a variety of options to suit every traveler's needs. Our friendly and knowledgeable staff is dedicated to providing top-notch service and ensuring a memorable stay for all our guests. Experience the ultimate tropical getaway at Anglers Reef Vacation Rental.

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.

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.

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.

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!