The 30 Best Adventurous vacations in Islamorada, Florida

Located at 84001 Overseas Highway in Islamorada, Florida, the Islamorada Dive Center is your go-to destination for all things ocean adventure. As part of the Scuba Town USA family, we offer a wide range of activities for the whole family, including scuba diving charters, courses, snorkeling, spearfishing, shark encounters, and more. Our experienced and friendly guides, instructors, and crew are dedicated to providing you with the best experience possible during your visit to the Keys. Whether you're a seasoned diver or a beginner, our team at Islamorada Dive Center is committed to ensuring a safe and enjoyable experience for all. With top-notch equipment, skilled staff, and breathtaking underwater life to explore, you're guaranteed to have a memorable and exciting time with us.

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 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.

Islamorada Ocean Oasis is a premier real estate and travel agency located at 75831 Overseas Highway in Islamorada, Florida. Our team of dedicated professionals specialize in providing clients with luxurious oceanfront properties and unforgettable travel experiences in the stunning Florida Keys. Whether you are looking to invest in a beachfront paradise or plan your dream vacation, Islamorada Ocean Oasis is here to make your dreams a reality. Contact us today to start your journey to paradise.

Barefeet Vacation Rentals is a real estate and travel agency located at 103400 Overseas Highway in Key Largo, Florida. Specializing in Key Largo and Islamorada vacation rentals, Barefeet Rentals offers a variety of private homes and condos to fit any budget, some even featuring docks for boaters. Whether you're a boater, fisherman, scuba diver, sun worshiper, or snowbird, Barefeet Rentals has something for everyone in the fabulous Florida Keys. From snorkeling coral reefs to deep-sea fishing excursions, there are endless activities to enjoy in this tropical paradise. Explore the Everglades National Park on an airboat tour or kayak through the Florida Keys for a unique eco-adventure.

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.

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.

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!

Aquablue Adventures is a premier travel agency located in the beautiful coastal town of Islamorada, Florida. Situated at 85501 Overseas Highway, our agency specializes in creating unforgettable aquatic experiences for our clients. Whether you're looking to explore the crystal-clear waters of the Florida Keys or embark on a thrilling deep-sea fishing excursion, our team of experienced travel experts is dedicated to planning the perfect adventure for you. From snorkeling with vibrant marine life to sailing along the stunning coastline, Aquablue Adventures is your gateway to the ultimate aquatic escape. Contact us today to start planning your next unforgettable journey.

Sea The Keys Island Adventures is a premier travel agency located in the beautiful coastal town of Islamorada, Florida. Specializing in unique and unforgettable island adventures, our team of experienced professionals is dedicated to providing top-notch service and creating unforgettable experiences for our clients. Whether you're looking to explore the stunning underwater world of the Florida Keys, embark on a thrilling fishing excursion, or simply relax on a pristine beach, Sea The Keys Island Adventures has something for everyone. Let us help you plan the perfect island getaway and make memories that will last a lifetime.

The Islamorada Visitors Centre is a travel agency located at 50 Russell Street in Islamorada, Florida. This center serves as a one-stop destination for tourists seeking information, assistance, and resources for exploring the beautiful surroundings of Islamorada. From booking accommodations to planning excursions, the friendly staff at the Visitors Centre are dedicated to helping visitors make the most of their time in this tropical paradise. Whether you're looking for recommendations on local attractions, dining options, or outdoor activities, the Islamorada Visitors Centre is your go-to resource for all things travel-related in this charming seaside town.

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.

The Islamorada Chamber of Commerce & Visitors Center is a travel agency located at 87100 Overseas Highway in Islamorada, Florida. As the gateway to the beautiful Florida Keys, this institution serves as a one-stop destination for tourists and locals alike looking for information on local businesses, attractions, events, and accommodations. Whether you're planning a vacation, a weekend getaway, or just passing through, the friendly staff at the Islamorada Chamber of Commerce & Visitors Center are ready to assist you with all your travel needs. Visit us today and let us help you make the most of your time in this tropical paradise.

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.

Sand Hopper Adventure Tours LLC is a premier adventure tour company located at 76777 Overseas Highway in Islamorada, Florida. We offer a variety of exciting experiences for the whole family, including Florida Keys family fishing, visits to the Islamorada sandbar, snorkeling at the Alligator Reef Lighthouse, boat tours, custom tours, and more! Book your private charter today with Sand Hopper Adventures and experience the beauty of Islamorada and Key Largo in Florida. Contact Captain Rob directly for an immediate response and start planning your unforgettable adventure on the water.

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.

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.

Forever Young Charter Company is a premier travel agency located in the beautiful Islamorada, Florida. Our company offers a wide range of charter services for those looking to explore the stunning waters of the Florida Keys. Whether you're interested in deep sea fishing, snorkeling, or simply cruising along the coast, our experienced crew will ensure you have an unforgettable experience. Visit us at 80461 Overseas Highway and let us help you create memories that will last a lifetime.

Paddle the Florida Keys is a top-rated institution located in Tavernier, Florida, offering kayak and paddleboard rentals, eco-tours, sales, and deliveries. Whether you're a beginner or experienced paddler, our professional guides will lead you on an unforgettable journey through the beautiful mangrove tunnels and seagrass meadows of the Florida Keys. With flat rates and the option to rent for 24 hours or longer, you can paddle at your own pace and explore at your leisure. Owner Deven Carrier, a lifelong Keys local and competitive paddle board racer, is passionate about the sport and has helped grow the local paddlesport community for over a decade. Our retail store offers a wide selection of paddle boards, skateboards, gear, and accessories, ensuring you have everything you need for a day on the water or onshore.

Key Dives is a premier dive school and store located at 79851 Overseas Highway in Islamorada, Florida. Our institution offers a wide range of scuba diving courses for all skill levels, from beginners to advanced divers. Our experienced instructors provide personalized training in a safe and supportive environment. In addition to our courses, Key Dives also offers a variety of high-quality dive gear and equipment for purchase. Whether you are looking to learn how to dive or upgrade your gear, Key Dives is your go-to destination for all things scuba diving in the beautiful waters of Florida Keys.

A1A Watersports & Boat Rentals is a popular tourist attraction located at 85970 Overseas Highway in Islamorada, Florida. We offer a variety of boat rentals for you to explore the stunning waters of the Florida Keys. Please note that snorkel gear is not available for rental, so be sure to bring your own. Our location on the bayside at MM 85.9 makes us easily accessible, close to Venetian Shores and Snake Creek Bridge. Whether you're looking to fish, snorkel, or simply enjoy a day out on the water, A1A Watersports & Boat Rentals is the perfect place to start your adventure in the "Sport Fishing Capital of the World."

The Theater of the Sea is a unique park and tourist attraction located at 84721 Overseas Highway in Islamorada, Florida. This institution combines elements of a zoo and an entertainment venue, offering visitors the opportunity to interact with a variety of marine animals in a beautiful tropical setting. From dolphin and sea lion shows to guided tours and educational programs, Theater of the Sea provides a fun and informative experience for visitors of all ages. Come explore the wonders of the sea at this exciting attraction in the heart of the Florida Keys.

Saltwater Outfitters is a premier clothing store located at 81913 Overseas Highway in Islamorada, Florida. Specializing in high-quality outdoor apparel and gear, this store is a must-visit for anyone looking to explore the beautiful waters of the Florida Keys. From fishing and boating attire to beachwear and accessories, Saltwater Outfitters has everything you need for your next adventure on the water. With a wide selection of top brands and knowledgeable staff, this store is the go-to destination for all your outdoor clothing needs. Visit Saltwater Outfitters and gear up for your next coastal excursion!

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.

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.