TOP 30 Relaxing vacation in Islamorada, Florida

Islamorada Resort Wear is a premier clothing store located in the beautiful coastal town of Islamorada, Florida. Our store offers a wide selection of stylish resort wear for men and women, perfect for those looking to embrace the laid-back, beachy vibe of the Florida Keys. From flowy sundresses and colorful swimwear to casual shorts and breezy tops, we have everything you need to create the perfect vacation wardrobe. Visit us at 86700 Overseas Highway and shop the latest trends in resort wear today!

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.

Creekside Inn Islamorada is a charming lodging establishment located along the picturesque Old Highway in Islamorada, Florida. Surrounded by lush tropical gardens and just a stone's throw away from the crystal-clear waters of the Florida Keys, this inn offers a tranquil and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a refreshing dip in the outdoor pool, relax in the hot tub, or take a leisurely stroll along the nearby creek. With its convenient location and laid-back atmosphere, Creekside Inn Islamorada is the perfect choice for a memorable vacation in the Florida Keys.

Tropical Paradise in Venetian Shores is a luxurious retreat located at 141 Stromboli Drive in Islamorada, Florida. This stunning property offers guests a true taste of paradise with its lush tropical surroundings and breathtaking views. The resort features a heated pool, perfect for relaxing and soaking up the sun. Whether you're looking to unwind in style or explore the nearby attractions, Tropical Paradise in Venetian Shores is the perfect destination for your next getaway.

The Islands of Islamorada is a charming lodging institution located at 82779 Old Highway in Islamorada, Florida, United States. Nestled in the heart of the Florida Keys, this picturesque resort offers guests a serene and relaxing retreat surrounded by the beauty of the islands. With comfortable accommodations, stunning ocean views, and easy access to a variety of outdoor activities such as fishing, snorkeling, and kayaking, The Islands of Islamorada is the perfect destination for a peaceful getaway. Whether you're seeking a romantic escape or a family vacation, this institution provides a tranquil and unforgettable experience for all who visit.

The Sunset Inn in Islamorada, Florida is a charming lodging establishment located on the beautiful Overseas Highway. This cozy inn offers comfortable accommodations with a laid-back atmosphere, perfect for a relaxing getaway in the Florida Keys. Guests can enjoy stunning sunsets from the inn's private beach or take a dip in the crystal-clear waters of the Gulf of Mexico. With its convenient location near local attractions, restaurants, and shops, The Sunset Inn is the ideal choice for travelers looking to experience the best of Islamorada. Whether you're seeking a romantic retreat or a family vacation, this quaint inn provides a welcoming and peaceful escape.

Islamorada Vacation Rentals is a premier real estate agency located at 81610 Overseas Highway in Islamorada, Florida. Specializing in providing luxurious vacation rentals in the beautiful Florida Keys, our agency offers a wide range of properties to suit every traveler's needs. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious waterfront home, we have the perfect rental for your next getaway. Our dedicated team is committed to providing exceptional service and ensuring that your vacation in Islamorada is unforgettable. Book with us today and experience the ultimate in relaxation and luxury.

The Oasis of Islamorada is a charming shopping mall located at 81641 Old Highway in Islamorada, Florida. This unique destination offers a variety of shops and boutiques, perfect for finding one-of-a-kind treasures and gifts. Visitors can explore the beautifully landscaped grounds and enjoy a leisurely day of shopping, dining, and relaxation. Whether you're looking for the latest fashion trends, artisanal crafts, or delicious local cuisine, The Oasis of Islamorada has something for everyone. Come experience the laid-back atmosphere and tropical charm of this hidden gem in the Florida Keys.

Islamorada Boat Rentals is a premier boating institution located on the beautiful Overseas Highway in Islamorada, Florida. We offer a wide range of top-quality boats for rent, perfect for exploring the crystal-clear waters of the Florida Keys. Whether you're looking to cruise the coast, fish for trophy catches, or just relax and enjoy the stunning scenery, our knowledgeable staff will help you find the perfect vessel for your needs. With competitive rates and exceptional customer service, Islamorada Boat Rentals is your go-to destination for a memorable boating experience in the heart of the Florida Keys.

SuCasa Vacation Rentals is a charming lodging institution located at 77360 Overseas Highway in the picturesque town of Islamorada, Florida. Offering a variety of vacation rental options, SuCasa provides guests with a home away from home experience in the heart of the Florida Keys. Whether you are looking for a cozy cottage by the beach or a luxurious waterfront villa, SuCasa has the perfect accommodation for your vacation needs. With top-notch amenities, personalized service, and a convenient location near local attractions and activities, SuCasa Vacation Rentals is the ideal choice for a memorable stay in Islamorada.

Ted's Place Weekly Vacation Rental is a charming and elegant estate located at 140 Madeira Road in Islamorada, Florida. This hidden gem is nestled on the bayfront, offering a secluded retreat while still being close to the best of Islamorada both on land and water. This real estate and travel agency offers a unique blend of old Florida charm and modern elegance in a nature-rich tropical oasis. The property has a fascinating Florida history, adding a little extra heart and soul to your vacation experience - especially if you're a baseball fan or a fishing fanatic.

Coastal Vacation Rentals of the Florida Keys is a premier real estate and travel agency located at 82889 Overseas Highway in Islamorada, Florida, United States. We specialize in luxury vacation homes that exceed your expectations and cater to all your needs. Our extensive inventory includes weekly and monthly rentals, condos, villas, estates, corporate retreats, oceanfront and bayfront properties. Our personalized service sets us apart, ensuring that your vacation is a success no matter where you choose to stay in the Florida Keys. From breathtaking views to top-notch amenities, we have everything you need for a memorable getaway. Whether you're looking for a romantic escape or a family adventure, we have something for everyone.

Islamorada Turtle Tours LLC is a travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Cruise Islamorada aboard its newest, biggest, and best tour boat, "The Turtle", a custom-built 53ft XL Deck Boat that can accommodate up to 42 people. Explore beautiful Islamorada on one of our spectacular tours, departing daily from The Lorelei Restaurant & Cabana Bar. On our tours, you can enjoy a short cruise to the famous Islamorada sandbar, where you can walk along the sandy flat, float on giant mats, soak up the sun, and relax. Fun for all ages! You can also snorkel at one of Islamorada's beautiful shallow water reefs, with depths between 8-20 feet. The choice of reef location will depend on factors such as visibility and weather conditions.

Island Paradise Villas offers a luxurious and relaxing stay in the beautiful Florida Keys. Located at 75710 Overseas Highway in Islamorada, Florida, this vacation rental agency provides a range of stunning villas for visitors to choose from. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Island Paradise Villas has the perfect accommodation for you. With top-notch amenities, breathtaking ocean views, and convenient access to local attractions, this is the ideal destination for your next vacation in paradise. Book your stay with Island Paradise Villas for a truly unforgettable experience in the Florida Keys.

MyKeys Tours of Islamorada is a premier travel agency located at 85920 Overseas Highway in the picturesque town of Islamorada, Florida. Specializing in creating unforgettable experiences for visitors to the Florida Keys, our team of knowledgeable and friendly experts are dedicated to providing top-notch service and personalized itineraries. Whether you're looking to explore the stunning coral reefs, indulge in world-class fishing opportunities, or simply relax on the beautiful beaches, MyKeys Tours of Islamorada is here to help you plan the perfect vacation. Come visit us and let us show you the best that Islamorada has to offer!

Islamorada Island Tours is a travel agency located at 77522 Overseas Highway in Islamorada, Florida, United States. We specialize in boat rentals, Jetski tours, and private Island tours, available 7 days a week. Whether you're looking for a relaxing day on the water or an adventurous excursion, we have the perfect boat for you. Our docks are conveniently located within 7 miles of eight amazing points of interest. Contact us at 305-664-5533 to discuss your options and plans, or send us an email or live chat with us for more information. Let us help you create unforgettable memories on the beautiful waters of Islamorada.

Casa Rio Islamorada is a charming lodging institution located at 121 Sapodilla Drive in Islamorada, Florida. Nestled in the heart of the Florida Keys, this cozy retreat offers a peaceful and serene atmosphere for guests to relax and unwind. With comfortable accommodations and a welcoming staff, Casa Rio Islamorada is the perfect place to escape the hustle and bustle of everyday life. Whether you're looking for a romantic getaway or a family vacation, this hidden gem is sure to provide a memorable experience. Explore the beautiful surroundings, soak up the sun on the nearby beaches, or simply enjoy a leisurely stroll along the waterfront. Come and experience the laid-back charm of Casa Rio Islamorada for yourself.

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.

The Oceanview Inn & Sports Pub is a charming establishment located at 84500 Overseas Highway in Islamorada, Florida. This institution offers a unique combination of bar, food, and lodging, making it the perfect destination for a Keys vacation. The guest rooms at The Oceanview Inn & Pub are clean, comfortable, and have a tropical flair, providing guests with a relaxing and enjoyable stay. Whether you're visiting for a weekend getaway or a longer stay, this inn has everything you need for a perfect vacation.

SandBar is a lively and vibrant institution located at 83413 Overseas Highway in Islamorada, Florida. This beachfront bar and restaurant offers a relaxed and casual atmosphere where guests can enjoy delicious food, refreshing drinks, and stunning views of the ocean. With a diverse menu featuring fresh seafood, mouth-watering burgers, and tasty appetizers, SandBar is the perfect spot to unwind and enjoy a meal with friends and family. Whether you're looking to grab a quick bite or spend a leisurely afternoon soaking up the sun, SandBar is the ideal destination for a memorable dining experience in the heart of the Florida Keys.

Located at 80001 Overseas Highway in Islamorada, Florida, the Amara Cay Resort offers a luxurious and effortless island experience. From the chic coastal style of the rooms and suites to the breathtaking views of the Alligator Reef Lighthouse, every aspect of this resort embodies the essence of the Florida Keys. Guests can enjoy island-inspired cuisine and cocktails with stunning sea views, as well as a variety of amenities and activities such as boating excursions and beach lounging. Whether you're looking for a relaxing beach vacation or an adventurous day on the water, Amara Cay has something for everyone. With special offers for Florida and Georgia residents, military personnel, and other groups, there are plenty of opportunities to save on your stay. The resort also offers a range of activities, from beachside yoga to ocean adventures, as well as delicious dining options at the poolside Tiki Bar and other on-site restaurants.

Soggy Paws Pet Resort and Spa is a luxurious retreat for your furry friends located at 88165 Overseas Highway in Islamorada, Florida. Our resort offers top-notch accommodations and amenities for dogs and cats, including spacious suites, grooming services, and a variety of activities to keep your pets entertained and happy. With a team of experienced and caring staff members, Soggy Paws provides a safe and comfortable environment for pets to relax and enjoy their stay. Whether your pet needs a relaxing spa day or a fun-filled vacation, Soggy Paws Pet Resort and Spa is the perfect destination for all your pet care needs.

Island Trendz Boutique at Amara Cay Resort and Postcard Inn is a charming clothing store located at 80001 Overseas Highway in Islamorada, Florida. This boutique offers a curated selection of trendy and stylish clothing, accessories, and swimwear perfect for your vacation in the Florida Keys. With a relaxed island vibe and friendly staff, Island Trendz Boutique is the perfect place to shop for your next beach getaway. Whether you're looking for a new swimsuit, a cute sundress, or a unique souvenir to remember your trip, this boutique has something for everyone. Visit us today and experience the laid-back luxury of Island Trendz Boutique at Amara Cay Resort and Postcard Inn.

Island Dreamz is a vibrant and trendy clothing store located at 84001 Overseas Highway in Islamorada, Florida. This coastal-inspired boutique offers a wide selection of stylish and comfortable clothing for both men and women. From flowy sundresses to beach-ready swimwear, Island Dreamz has everything you need to create your perfect island getaway wardrobe. With its laid-back atmosphere and friendly staff, shopping at Island Dreamz feels like a dream come true. Visit us today and let us help you find the perfect pieces to make your island dreams a reality.

Located at 81801 Overseas Highway in Islamorada, Florida, Cheeca Lodge & Spa offers a luxurious retreat surrounded by turquoise waters, towering palms, and calm breezes. This oceanfront resort invites guests to experience barefoot luxury and embrace the laid-back lifestyle of the Florida Keys. With a range of thrilling activities, luxurious accommodations, exceptional dining options, and unparalleled relaxation, Cheeca Lodge & Spa promises an unforgettable getaway. Whether you're looking to celebrate love with a picturesque oceanfront wedding or host a productive corporate retreat, Cheeca Lodge & Spa offers the perfect venue. With over 15,000 square feet of meeting space, impeccable service from event planners, and a stunning backdrop of the Atlantic ocean, this resort is ideal for weddings, sales meetings, conferences, and more.

Located at 84001 Overseas Highway in Islamorada, Florida, the Postcard Inn Beach Resort and Marina offers a unique and authentic Keys experience. As the "Sportfishing Capital of the World," guests can bring their own boat or book an excursion to explore the waters surrounding this beautiful resort. With the merging of two Islamorada resorts into one destination, the Postcard Inn Resort & Marina is set to become the heartbeat of the Islamorada Resort Collection in 2024. Offering island-chic guestrooms, exciting culinary experiences, a lively marina, a stunning beachfront, and a variety of activities, guests can seamlessly transition between adventure and relaxation from sunrise to sunset.

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.

Drop Anchor Resort & Marina is a charming lodging establishment located at 84959 Overseas Highway in the beautiful Islamorada, Florida. This waterfront resort offers a serene and relaxing escape for guests looking to unwind and enjoy the stunning views of the Florida Keys. With comfortable accommodations, a marina for boat enthusiasts, and a range of amenities including a pool and beach access, Drop Anchor Resort & Marina is the perfect destination for a memorable vacation in the heart of the Keys.

Nestled in the picturesque town of Islamorada, Florida, Treasure Harbor is a charming lodging institution located at 200 Treasure Harbor Drive. Offering a tranquil and relaxing atmosphere, this hidden gem is the perfect destination for those seeking a peaceful getaway in the heart of the Florida Keys. With comfortable accommodations, stunning views of the harbor, and a range of amenities, including a pool and on-site restaurant, Treasure Harbor provides guests with a truly unforgettable experience. Whether you're looking to unwind by the water or explore the local attractions, Treasure Harbor is the ideal choice for your next vacation.

Ragged Edge Resort and Marina is a charming lodging establishment located at 243 Treasure Harbor Drive in the picturesque town of Islamorada, Florida. Situated right on the waterfront, this resort offers guests stunning views of the marina and the crystal clear waters of the Florida Keys. The resort features comfortable accommodations, a variety of amenities, and easy access to all the outdoor activities and attractions the area has to offer. Whether you're looking to relax by the pool, go fishing, or explore the local shops and restaurants, Ragged Edge Resort and Marina is the perfect place to unwind and enjoy a memorable vacation in paradise.