TOP 30 Best Island vacation deals in Destin, Florida

Banyan House Vacation Rentals is a charming Mediterranean-style lodging located at 519 Harbor Drive South in Venice, Florida. Step back in time and experience the old-world charm of one of Venice Island’s most historic homes. Guests can immerse themselves in peace and tranquility while enjoying the tropical gardens, Koi Pond, and majestic Banyan tree on the property. The award-winning vacation destination offers a range of amenities including a pool, hot tub, onsite gym, billiards and games room, elegant common areas, and comfortable accommodations. The institution is ideally located just a few blocks from historic downtown Venice, with its unique shops, restaurants, art galleries, theaters, parks, and beaches.

Grace River Island Resort is a hidden gem located at 14524 Riverside Drive in Fort Myers, Florida. This private tropical island vacation home is nestled on the Caloosahatchee River, accessible via a land bridge that transforms it into a peninsula. Whether you are looking for a memorable family vacation, a romantic honeymoon, an intimate wedding venue, or simply some time away, Grace River Island Resort offers the perfect setting. The resort features a spacious 6-bedroom, 8-bathroom house that can accommodate up to 20 guests, making it ideal for family reunions or group getaways. Guests can enjoy a large air-conditioned bonus room, a 2000 sq ft deck overlooking the river with market lighting, a heated swimming pool, a beautiful gazebo, an upscale courtyard, and a grassy point with stunning sunsets. The bridal suite upstairs is perfect for wedding preparations, while the groomsman area downstairs provides a space for the guys to relax before the ceremony.

Stay & Play Vacation Rentals and Watersports Clearwater Beach is a dynamic hospitality concept located at 657 Bay Esplanade in Clearwater, Florida. This all-inclusive vacation destination offers waterfront vacation rentals and a wide range of on-site activities and amenities. From jet skiing and parasailing to kayaking, paddle boarding, and fishing expeditions, there is something for everyone to enjoy. Guests can also explore the local sights with golf cart rentals. The institution also offers a unique stay-and-play experience with a custom-built houseboat rental located on the intracoastal Mandalay Bay, just two blocks from the Gulf of Mexico. Complimentary kayak and paddle board rentals, beach cruiser bikes, and beach equipment are provided to ensure a comfortable and enjoyable stay.

Destin Sailing Adventures is a travel agency located at 1201 Miracle Strip Parkway Southeast in Okaloosa Island, Florida, United States. Step aboard the Stiletto 27 Special Edition Catamaran for an unforgettable experience on the majestic waters of the Emerald Coast. Our boat is designed for maximum sailing pleasure and performance, perfect for adventure and racing enthusiasts. With a 20hp motor on board, we can ensure that you have an amazing time even if the wind isn't blowing. Our private charters come with a local captain to guide you to all the best spots in Destin, Okaloosa Island, and Navarre Beach. Whether you're looking for a relaxing sunset cruise, a thrilling dolphin tour, or a romantic marriage proposal setting, we have something for everyone. Avoid the crowds and enjoy a personalized experience with just your group on board. Book early to secure your spot and beat the summer rush!

FunShine Island Services LLC is a premier travel agency located on Starboard Drive in Bokeelia, Florida. Our dedicated team of travel experts is committed to providing exceptional service and creating unforgettable experiences for our clients. Whether you're looking to book a tropical getaway, a romantic honeymoon, or a family vacation, we are here to help you plan the perfect trip. From luxury accommodations to exciting excursions, FunShine Island Services LLC has everything you need to make your travel dreams a reality. Contact us today to start planning your next adventure!

Crab Island Tiki Boats is a popular tourist attraction located at 316 Harbor Boulevard in Destin, Florida. Visitors can enjoy a unique and fun experience on the water aboard tiki-style boats, complete with thatched roofs and tropical decor. Cruise around the beautiful waters of Destin, soaking up the sun and enjoying the stunning views of the Gulf Coast. Whether you're looking for a relaxing day on the water or a lively party atmosphere, Crab Island Tiki Boats offers something for everyone. Don't miss out on this one-of-a-kind experience during your visit to Destin!

Bay Harbor One Vacation is a premier lodging and real estate agency located at 1100 100th Street in the beautiful Bay Harbor Islands of Florida, United States. Our institution offers luxurious vacation rentals and properties for sale in one of the most sought-after destinations in South Florida. With stunning waterfront views, top-notch amenities, and a prime location near shopping, dining, and entertainment options, Bay Harbor One Vacation is the perfect choice for a relaxing getaway or a permanent residence in paradise. Come experience the ultimate in luxury living at Bay Harbor One Vacation.

Virgin Island Sailing® is a renowned travel agency located at 8900 North Armenia Avenue in Tampa, Florida, United States. With over 30 years of experience, we specialize in providing world-class yacht charters and sailing vacations in destinations such as the Caribbean, Mediterranean, South Pacific, and more. Our team is dedicated to ensuring that your sailing trip is trouble-free and unforgettable. Whether you're looking for a romantic retreat, a family adventure, or a fun getaway with friends, Virgin Island Sailing® offers a wide selection of sailboats, catamarans, motor yachts, and luxury yachts to suit your preferences. Our partnerships with reputable charter companies and crewed yacht management companies ensure that we only recommend the best yachts and crews in the industry.

Welcome to On Island, your ultimate gateway to the vibrant life of Sanibel and Captiva Islands. Conveniently located at 975 Rabbit Road, Sanibel, Florida 33957, our store is your one-stop destination for all things island-related. Immerse yourself in the spirit of the islands with our curated selection of island gear that lets you carry a piece of paradise wherever you go. At On Island, we are more than just a store; we are your connection to the heart of Sanibel and Captiva. Stay updated with our local "news" and enjoy stunning pictures that capture the essence of island life. Our insider guide, crafted by locals, offers you the best recommendations on where to eat, play, and stay, ensuring you experience the islands like a true native.

Welcome to Pass-a-Grille Beach House Vacation Rental, located at 2202 Sunset Way in St. Pete Beach, Florida. Our institution offers a range of rental properties perfect for a romantic getaway or a family-friendly vacation. Pass-a-Grille Beach Island is a captivating destination, consistently ranked among the top beaches in the United States. The pristine white sands, historical charm, and recreational opportunities make it a must-visit location. Explore the historic area with specialty shops and vibrant bars, or indulge in the local cuisine at beachfront restaurants with panoramic views of the Gulf of Mexico. Immerse yourself in the rich history of the area at the Gulf Beaches Historical Museum and discover the captivating past that has shaped this idyllic coastal community.

Crab Island is a popular floating water park and party spot located in Destin, Florida, United States. This unique institution offers visitors the opportunity to relax and have fun in the crystal-clear waters of the Gulf of Mexico. With various water activities, such as paddleboarding, kayaking, and snorkeling, Crab Island is the perfect destination for those looking to enjoy a day out on the water. Visitors can also enjoy delicious food and drinks from the various vendors and restaurants located on the floating platforms. Whether you're looking to soak up the sun or dance to live music, Crab Island has something for everyone to enjoy.

The Sanibel & Captiva Islands Chamber of Commerce is a travel agency located at 1159 Causeway Boulevard in Sanibel, Florida, United States. Despite the damage caused by Hurricane Ian in September 2022, the islands are quickly recovering and remain a beautiful destination for visitors. The Chamber provides information on open businesses, hotels, restaurants, and activities on both Sanibel and Captiva Islands. Whether you're looking for a relaxing beach vacation or outdoor adventures like biking, fishing, and bird watching, these islands offer a unique and serene experience. The Chamber also offers resources for real estate, dining options, shopping, and more. Visit the Chamber's Visitor Center for assistance in planning your trip to these picturesque islands.

Crab Island Runner and Destin Dolphin Tours offers an unforgettable experience in Destin, Florida. Located at 7 Calhoun Avenue, this institution provides comfortable and fast Yamaha VX Deluxe Jet Skis with a breaking system and boarding ladders. Enjoy a ride next to Crab Island with no idle time, as you explore Destin Harbor, East Pass, Crab Island, Choctawhatchee Bay, and get up close and personal with dolphins. Bachelorette Packages Upgrades are also available for those looking to celebrate special occasions. With licensed captains ensuring your safety and relaxation, you can spend quality time cruising through the emerald green waters, fishing, or relaxing on Crab Island. The personalized dolphin tour allows you to get up close and personal with these amazing creatures, with dolphins often coming right up to you. Parasailing offers a bird's eye view of the stunning Destin skyline, while witnessing dolphins playing in the crystal clear waters.

Gulf Islands National Seashore, located in Gulf Breeze, Florida, is a popular destination for millions of visitors seeking the beauty of the Gulf of Mexico. With its emerald coast waters, stunning white beaches, lush marshes, and historical sites, this campground, lodging, and park offers a wide range of activities for all ages to enjoy. From exploring the beaches, trails, and forts to renting pavilions for special events, there is something for everyone at Gulf Islands National Seashore. Fees may apply for entrance and pavilion rentals, so be sure to reserve your campsite in advance for direct access to all the attractions. Whether you choose to visit the mainland or one of the barrier islands, you'll have the opportunity to discover hidden gems away from the crowds. Before your visit, make sure to familiarize yourself with the rules and regulations of the national seashore to ensure a safe and enjoyable experience. Come explore the natural beauty and rich history of Gulf Islands National Seashore today!

Gulf Islands Ferry: Your Gateway to the Best of Bradenton and Anna Maria Island Located on Gulf of Mexico Drive in beautiful Longboat Key, Florida, Gulf Islands Ferry offers a seamless and scenic transportation experience between Bradenton and Anna Maria Island. Say goodbye to traffic woes and hello to breathtaking views as you cruise across the water to your island adventure.

The St George Island Florida Beach Cam is a must-visit destination located on the beautiful Saint George Island in Florida, United States. This institution offers a unique experience for visitors to enjoy the stunning views of the beach through their live webcam. Whether you're planning a trip to the area or simply want to take in the beauty of the beach from afar, the St George Island Florida Beach Cam is the perfect place to do so. Stop by this store and travel agency to get all the information you need for your visit to this picturesque location.

Off the Charts Inn & Out Island Resort is a unique and trendy establishment located at 2938 Sanibel Boulevard in Saint James City, Florida. This one-of-a-kind institution offers a combination of a clothing store, lodging, and store all in one convenient location. Guests can shop for the latest fashion trends, relax in comfortable accommodations, and browse through a variety of merchandise all under one roof. The resort is known for its laid-back atmosphere, friendly staff, and beautiful island surroundings.

Club Regency of Marco Island is a cozy gem located on Florida's Gulf Coast, offering 2-bedroom suites with full kitchens and outdoor spaces. Guests can enjoy a private pool, sport courts, and beach access, making it the perfect retreat for families. The spacious suites feature screened lanais, fully equipped kitchens, and comfortable living areas. On-site amenities include tennis, shuffleboard, and basketball courts, while nearby attractions such as restaurants, boutiques, golf courses, and historic sites provide plenty of entertainment options. Membership with Hilton Grand Vacations is also available for those interested in timeshare ownership. Prices range from $7,800 to $758,990 for deeded interest, with additional options for U.S. and Hawaii Collections and Embarc Collection. Restrictions and financing requirements apply, and offerings may vary by location. Hilton Grand Vacations is a registered trademark of Hilton Worldwide Holdings Inc. and operates under a license agreement.

Treasure Island Beach is a popular tourist attraction located at 11260 Gulf Boulevard in Treasure Island, Florida, United States. This stunning beach offers pristine white sands, crystal clear waters, and breathtaking views of the Gulf of Mexico. Visitors can enjoy sunbathing, swimming, beachcombing, and water sports such as paddleboarding and parasailing. The beach is also lined with shops, restaurants, and hotels, making it the perfect destination for a relaxing day by the sea. Whether you're looking to unwind and soak up the sun or enjoy some fun in the water, Treasure Island Beach has something for everyone.

Destin Crab Island Adventures is a premier tourist attraction and travel agency located at 7 Calhoun Avenue in Destin, Florida. Offering unforgettable experiences on the crystal-clear waters of Crab Island, visitors can embark on exciting adventures such as snorkeling, paddleboarding, and jet ski tours. With knowledgeable guides and top-of-the-line equipment, guests can explore the stunning natural beauty of the area and create lasting memories. Whether you're looking for a relaxing day on the water or an adrenaline-pumping excursion, Destin Crab Island Adventures has something for everyone. Book your next adventure with us and discover the magic of Destin's famous Crab Island!

Blue Crab Water Sports of Destin is the ultimate destination for those looking to experience the best of the Emerald Coast's waters. Located at 404 Harbor Boulevard in Destin, Florida, this tourist attraction offers a variety of water sport rentals including jet skis and pontoon boats. By renting in advance, visitors can secure their vessel and guarantee a memorable trip on the water. Whether you want to explore the Destin Harbor, cruise the Choctawhatchee Bay, or party at Crab Island, Blue Crab Water Sports has top-of-the-line equipment to make your experience unforgettable. Conveniently situated just 10 minutes from Crab Island, this institution is the perfect place to gather your crew and enjoy a day of fun in the sun. Don't miss out on the opportunity to make a splash and soak up the sun at Blue Crab Water Sports of Destin.

Suntide Island Beach Club is a charming beachfront lodging institution located at 850 Benjamin Franklin Drive in Sarasota, Florida, United States. This tropical oasis offers guests a relaxing and rejuvenating stay with its cozy accommodations and stunning views of the Gulf of Mexico. The resort features a variety of amenities including a heated outdoor pool, beach access, BBQ grills, and complimentary Wi-Fi. Whether you're looking to unwind on the sandy shores, explore the local attractions, or simply soak up the sun, Suntide Island Beach Club is the perfect destination for your next vacation getaway.

Florida Vacation Connection is a premier lodging, real estate, and travel agency located at 3720 Gulf of Mexico Drive in Longboat Key, Florida. We specialize in providing top-notch vacation rentals, real estate services, and travel accommodations for those looking to experience the beauty and excitement of Florida. Our team of experienced professionals is dedicated to helping clients find the perfect vacation rental, buy or sell property, and plan unforgettable travel experiences in this stunning destination. Whether you're looking for a beachfront condo, a luxury estate, or a customized vacation package, Florida Vacation Connection has everything you need to make your Florida getaway truly unforgettable.

Vacation Villas at Longboat Key Club offers luxurious and spacious accommodations on the stunning Longboat Key in Florida. Situated at 220 Sands Point Road, this lodging institution provides guests with a perfect blend of relaxation and upscale amenities. With breathtaking views of the Gulf of Mexico and top-notch service, guests can enjoy a truly unforgettable vacation experience. Whether you're looking to unwind by the pool, play a round of golf, or explore the nearby attractions, Vacation Villas at Longboat Key Club is the perfect destination for a memorable getaway.

Orange Lake Resort River Island is a luxurious lodging establishment located in Kissimmee, Florida. Situated at 8505 West Irlo Bronson Memorial Highway, this resort is the perfect destination for those looking for a relaxing and enjoyable vacation experience. The resort offers a wide range of amenities including spacious accommodations, multiple pools, a lazy river, on-site dining options, and a variety of recreational activities for guests of all ages. Whether you are looking to unwind by the pool or explore the nearby attractions, Orange Lake Resort River Island has something for everyone. Book your stay now and experience the ultimate in comfort and hospitality in the heart of sunny Florida.

Treasure Island Beach Resort is a luxurious lodging destination located at 10800 Gulf Boulevard in the beautiful Treasure Island, Florida. This beachfront resort offers stunning views of the Gulf of Mexico and provides guests with a tranquil and relaxing atmosphere. The resort features modern and stylish accommodations, including spacious rooms and suites with upscale amenities. Guests can enjoy a variety of on-site facilities such as a heated outdoor pool, fitness center, and beach access. The resort's prime location also allows guests to easily explore the nearby attractions, restaurants, and shopping options. Whether you are looking for a romantic getaway or a fun family vacation, Treasure Island Beach Resort provides the perfect setting for a memorable stay.

Sunshine Island Inn is a charming lodging located at 642 East Gulf Drive in Sanibel, Florida. This cozy inn offers a peaceful retreat for guests looking to relax and unwind in a tropical paradise. With its convenient location just steps away from the beach, guests can enjoy easy access to the sun, sand, and surf. The inn features comfortable accommodations, friendly staff, and a welcoming atmosphere that will make you feel right at home. Whether you're seeking a romantic getaway or a family vacation, Sunshine Island Inn is the perfect destination for your next trip to Sanibel.

Located at 4700 Amelia Island Parkway in Florida, United States, The Golf Club of Amelia Island is the premier choice for those seeking a private club experience on one of the most stunning barrier islands along the East Coast. With updated amenities and a picturesque setting, members can enjoy gourmet and casual dining options both indoors and outdoors, relax by the pool, play tennis, or take on the challenging 18-hole championship golf course. While there are other clubs in the Amelia Island area, such as Amelia River and National Golf Club, we believe that The Golf Club of Amelia Island is the perfect destination for you.

Happy's Crab Island Watersports is the ultimate destination for all your water adventure needs in Destin, Florida. Located at 316 Harbor Boulevard, we offer the best Pontoon Rentals in town with our Harris Kayot Pontoon Boats. Take your family out for a day of fun as you captain your own boat on the beautiful waters of the Emerald Coast. Experience the thrill of riding Yamaha Waverunners with your friends and family. Whether you prefer a leisurely sightseeing cruise or an adrenaline-pumping ride, Happy's Crab Island Watersports has something for everyone. Don't miss out on our guided dolphin excursions for a truly unforgettable experience.

The Islander is a real estate agency located at 502 Gulf Shore Drive in Destin, Florida. Take advantage of our Spring Savings promotion and save up to 20% on stays of 3 nights or more between April 6th and May 3rd, 2024. Our family-friendly condo rental resort on Holiday Isle offers stunning views of the Gulf of Mexico and Destin Pass/Lake Christine. Enjoy our private beach with free beach services, two pools (heated when needed), hot tubs, tennis court, pickleball courts, and basketball half-court. Guests can also access equipment from the on-site front desk. Our resort is close to championship golf courses, attractions, dining, and shopping in Destin. All guests receive an Islander Beach Resort VIP Pass for special discounts. The Islander is the perfect location for a destination wedding, with a newly remodeled event space overlooking the Gulf. Let us help you find your new favorite Destin condo for your next vacation! Visit us at 502 Gulf Shore Drive, Destin, FL 32541.