The 30 Best Florida keys vacations in Islamorada, Florida

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Rich Trottnow is a real estate agency located at 81579 Old Highway in Islamorada, Florida, United States. Specializing in upscale homes and condos with spectacular views and amenities, Island Management, owned by Judy Rossignol, offers top-notch customer service and attention to detail for both renters and homeowners. With a team of experienced agents, including Rich Trottnow, clients can trust that their property will be well cared for in their absence. Whether you are looking to rent a vacation home for a week or longer, or seeking to maximize the return on your investment property, Island Management is the perfect choice. Additionally, Judy Rossignol and her team at Realty One Group Engage the Keys are available to assist with buying or selling real estate in the Florida Keys. Contact Island Management today to find your next vacation home or discuss property management options.

The Heart of Morada is a unique institution located at 81906 Overseas Highway in Islamorada, Florida. As a real estate agency, we specialize in helping clients find their dream homes in this beautiful coastal town. Our team of experienced agents is dedicated to providing personalized service and expert guidance throughout the buying or selling process. In addition to our real estate services, we also operate as a travel agency, offering vacation rental properties and booking assistance for those looking to explore all that Islamorada has to offer. Whether you're searching for a permanent residence or a temporary getaway, the Heart of Morada is here to help you find the perfect property to suit your needs.

Little Basin Villas is a premier real estate and travel agency located in the picturesque Islamorada, Florida. Situated at 84 Johnston Road, our institution offers luxurious villas for rent or purchase in this stunning seaside town. Whether you are looking for a vacation rental or a permanent residence, our team of experts is dedicated to helping you find the perfect property to suit your needs. With a focus on personalized service and attention to detail, Little Basin Villas is the ideal choice for those seeking a slice of paradise in the Florida Keys. Contact us today to start your journey towards owning or renting your dream villa in Islamorada.

Anchors Away Boat Rentals is a tourist attraction located in Tavernier, Florida, United States. Serving Islamorada, Key Largo, Tavernier, and Marathon, they offer the perfect solution for experiencing all that the Florida Keys has to offer by getting out on the water. Special discounted rates are available for Military, Law Enforcement, and Fire Fighters. To enhance your experience, they offer rental add-ons such as fishing poles and a GoPro Hero 9 with an 8gb SD card that you get to keep. All boats are equipped with brand new Garmin navigation systems to ensure you can easily navigate to your favorite spots.

Rental Boat Co is a premier boat rental company located at 79851 Overseas Highway in Islamorada, Florida. We offer a wide selection of high-quality boats for rent, perfect for exploring the beautiful waters of the Florida Keys. Whether you're looking for a relaxing day of fishing, a thrilling ride on a speedboat, or a leisurely cruise to enjoy the sunset, Rental Boat Co has the perfect vessel for you. Our experienced and friendly staff are dedicated to providing top-notch customer service and ensuring you have a safe and enjoyable boating experience. Come visit us at Rental Boat Co and start your adventure on the water today!

Safe Harbor Angler House is a premier storage facility located at 80500 Overseas Highway in Islamorada, Florida. As a member of Safe Harbor, you will have access to a network of premium locations, amenities, events, and boating lifestyle opportunities. Located near the Florida Everglades National Park Marine Sanctuary, Safe Harbor Angler House is the perfect place for those who love to explore the largest subtropical wilderness in the United States. The sanctuary is home to a variety of endangered species, making it a must-visit destination for nature enthusiasts.

American Caribbean Real Estate is a premier real estate agency located at 81800 Overseas Highway in Islamorada, Florida. With over 30 years of experience in the Florida Keys real estate market, we have built a reputation for integrity, professionalism, and unparalleled market expertise. Our two locations in Islamorada and Key Largo cater to buyers and sellers looking for the perfect property in the Keys. As an industry leader in the Florida Keys marketplace, we have closed billions of dollars in sales and listings. Our dedicated sales team and administrative staff are committed to exceeding the expectations of our clients. One of our unique strengths is our affiliation with Christie's International Real Estate, the world's luxury real estate leader. This affiliation recognizes our superb performance in marketing and selling the most prized residences in the Florida Keys.

The Beach House at Tarpon Point is a luxurious oceanfront home located at 77521 Overseas Highway in Islamorada, Florida. This stunning property offers amazing ocean views, a sandy beach, pool, and an observation pier perfect for watching sunrises and sunsets. As a real estate and travel agency, The Beach House provides top-notch amenities and furnishings to ensure a relaxing and memorable vacation experience for all guests. Whether you're looking for a peaceful retreat or a fun-filled getaway, The Beach House at Tarpon Point is the perfect destination for your next trip to the beautiful Florida Keys.

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.

Welcome to The "Nest" Villa, located at 82236 Overseas Highway in Islamorada, Florida. Our villa is the perfect home away from home for your next Florida Keys vacation. Situated in a central part of Islamorada, our property is close to local attractions, shops, bars, and restaurants, many of which are within walking distance. Our villa is one of only seven units on the property, nestled on a shaded one-acre tropical hammock that stretches from the highway down to the beautiful shores of Florida Bay. The villa is secluded and private, with stunning views of the water and spectacular sunsets.

Beacon Reef Condominiums is a luxurious waterfront property located at 83201 Old Highway in Islamorada, Florida. These stunning condominiums offer breathtaking views of the ocean and are surrounded by lush tropical landscaping. Residents can enjoy resort-style amenities such as a pool, fitness center, and private beach access. The spacious units feature modern finishes and open floor plans, perfect for entertaining guests or relaxing in style. With its prime location in the heart of the Florida Keys, Beacon Reef Condominiums is the perfect place to call home for those seeking a peaceful and upscale coastal lifestyle.

The Oasis is a unique institution located at 82703 Old Highway in Islamorada, Florida. As a combined real estate and travel agency, we specialize in providing our clients with exceptional service and guidance in all aspects of buying, selling, or renting properties in the beautiful Florida Keys. Our team of experienced professionals is dedicated to helping you find your own personal oasis in this tropical paradise. Whether you are looking for a vacation rental, a permanent residence, or a lucrative investment property, The Oasis is here to make your real estate dreams a reality. Contact us today to start your journey to paradise.

Venetian Tropics is a luxurious lodging and real estate agency located at 106 San Remo Drive in the stunning Islamorada, Florida. Nestled in the heart of the Florida Keys, this institution offers a unique blend of tropical charm and Venetian elegance. Whether you are looking for a relaxing vacation rental or seeking to invest in a piece of paradise, Venetian Tropics has a team of expert agents ready to assist you. With a prime location near the turquoise waters of the Atlantic Ocean, guests and clients alike can enjoy the ultimate tropical getaway experience. Book your stay or find your dream property with Venetian Tropics today!

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.

CENTURY 21 Circle is a reputable real estate agency located at 86000 Overseas Highway in Islamorada, Florida, United States. With a team of experienced and knowledgeable agents, they specialize in helping clients buy and sell properties in the beautiful Florida Keys. Whether you are looking for a vacation home, investment property, or your dream waterfront estate, CENTURY 21 Circle is dedicated to providing top-notch service and finding the perfect property to meet your needs. Contact them today to start your real estate journey in paradise.

KeyZ Charters is a premier tourist attraction and travel agency located at 77522 Overseas Highway in Islamorada, Florida. Offering a variety of private boat tours and charters, KeyZ Charters is the perfect choice for exploring the Florida Keys, Everglades National Park, and South Florida. From snorkeling adventures to sunset cruises, bird-watching excursions, and eco-tours, KeyZ Charters provides exhilarating experiences for the whole family. Located in South Florida, KeyZ Charters can take you up close to popular landmarks such as Indian Key, Lignumvitae Key, Alligator Reef lighthouse, and Everglades National Park. Our experienced guides will ensure you have a memorable experience while observing local wildlife and enjoying the natural beauty of the area.

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.

I Can See CLEAR Kayaking is a unique travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Specializing in clear kayaking adventures, they offer a one-of-a-kind experience where guests can explore the crystal-clear waters of the Florida Keys while paddling through mangrove forests and coral reefs. With knowledgeable guides and top-of-the-line equipment, I Can See CLEAR Kayaking provides a safe and unforgettable journey for nature lovers and adventure seekers alike. Join them for a truly immersive and mesmerizing kayaking experience unlike any other.

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.

Berkshire Hathaway HomeServices Freewheeler Realty is a premier real estate agency located at 85992 Overseas Highway in Islamorada, Florida. With a focus on providing exceptional service and expertise in the local real estate market, our team of experienced agents are dedicated to helping clients find their dream home or investment property in the beautiful Florida Keys. In addition to our real estate services, we also offer travel assistance to those looking to explore the stunning surroundings of Islamorada. Whether you're looking to buy, sell, or rent, Berkshire Hathaway HomeServices Freewheeler Realty is here to help make your real estate dreams a reality.

Allergic to Land Charters is a travel agency located at 84371 Overseas Highway in Islamorada, Florida, United States. Led by Captain Sue DuBon, a seasoned mariner with over 40 years of experience, this agency offers exclusive aquatic adventures in the heart of the Florida Keys. Whether you're interested in snorkeling at vibrant coral reefs, enjoying serene sunset cruises, or exploring eco-friendly tours, Allergic to Land Charters promises unforgettable experiences on the water. With a spacious 22′ Twin Vee Catamaran, Captain Sue provides personalized tours tailored to your interests, ensuring a memorable journey every time. From snorkeling adventures to eco-tours and private excursions, each trip is designed to showcase the natural beauty of the Florida Keys. With over 300 5-star reviews, guests rave about the incredible experiences they've had with Captain Sue and her team. Whether you're a family looking for a fun day out or an enthusiast eager to explore the sea, Allergic to Land Charters offers the perfect adventure for everyone. Book your tour today and discover the wonders of the Florida Keys with Captain Sue DuBon at the helm.

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.

Wild Dolphin Tours is a travel agency located at 80001 Overseas Highway in Islamorada, Florida, offering a variety of boat tours for your enjoyment. Take advantage of our SPRING SALE PRICING and choose from options such as Islamorada Sandbar, Snorkel, Eco Tours, Sightseeing Tours, and more. We also offer Go Pro Camera & Wet Suit Rentals for your convenience. Our Large Group Boat Charter can accommodate 7 to 12 passengers on our 2 boats, providing a more intimate experience compared to larger boats. Explore the beautiful coral reefs of Islamorada and spot tropical fish like angelfish, damselfish, and parrot fish during our Snorkel & Sandbar Charters. Depending on sea conditions, we may visit Alligator Lighthouse, Cheeca Rocks, or Hen & Chickens for snorkeling.

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.

Blu Dog Charters is a travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Specializing in private charters, they offer a variety of tours including snorkeling, sandbar trips, sunsets, BBQ excursions, sightseeing, lobster hunting, fishing, eco tours, and bar hopping adventures. Captain Steve, a seasoned mariner with experience in the United States Coast Guard and Merchant Marines, leads the trips and is known for his love of the ocean and bad jokes. The newest addition to their fleet, Serenity Blu, is now available for bookings.

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.

Skins and Fins Charters is a premier tourist attraction and travel agency located at 81924 Overseas Highway in Islamorada, Florida. Specializing in fishing charters and guides in the Florida Keys, Skins and Fins offers a unique experience for anglers of all levels. Captain Ted Benbow, a skilled fisherman and Florida Keys native, has over 20 years of experience fishing the waters of Key Largo, Islamorada, Marathon, and the Everglades. With a focus on families and trips with kids, Captain Ted provides stress-free instructions and tips for both novice and experienced anglers. Targeting a variety of species including tarpon, redfish, snook, shark, and bonefish, guests are guaranteed an enjoyable and fun day on the water. Father and son fishing team, Captain Donnie, is a second-generation captain with a lifelong passion for fishing. With over ten years of experience as a licensed captain, Captain Donnie offers a unique and educational fishing experience for guests of all ages. Whether you're looking for your first catch or a dream fishing adventure, Captain Donnie will go above and beyond to ensure a memorable experience on the water.

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!