TOP 30 Best Island vacation in Clearwater, Florida

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.

Crab Island Dolphin Tours is a premier travel agency located at 314 Harbor Boulevard in Destin, Florida, United States. Our expert guides will take you on an unforgettable adventure to see dolphins up close in their natural habitat. Join us for a thrilling and educational experience as we cruise through the crystal-clear waters of the Gulf of Mexico. Book your tour today and create memories that will last a lifetime.

Welcome to Clearwater Beach Jet Ski Tours, your premier destination for thrilling water adventures in the heart of Clearwater, Florida! Nestled at the beautiful Barefoot Bay Resort and Marina, 401 East Shore Drive, we offer expertly guided Jet Ski tours that promise excitement for the entire family. Experience the Gulf's warm, crystal-clear waters and the stunning scenery of Clearwater Beach and its surrounding barrier islands. Our tours balance adrenaline-pumping open-water rides with serene cruising for a comprehensive and unforgettable experience. Whether you're a thrill-seeker or prefer a leisurely ride, our tours cater to all preferences and skill levels.

Clearwater Tiki Boat Tours is a unique travel agency located at 25 Causeway Boulevard in Clearwater, Florida. Step aboard one of their charming tiki boats and embark on a picturesque tour of Clearwater's stunning waterways. Enjoy the tropical atmosphere as you cruise along the coast, taking in the sights and sounds of this beautiful destination. With experienced guides and top-notch service, Clearwater Tiki Boat Tours offers an unforgettable experience for visitors looking to explore the area in style. Book your tour today and make memories that will last a lifetime.

Clearwater Party Boats, located at 445 East Shore Drive in Clearwater, Florida, is a travel agency that offers private and public boat tours customized to meet your needs. With options for up to 22 passengers, they can accommodate small and large groups, taking care of all the details and driving so you can relax and enjoy the day. Whether you're looking for a party on the water or a tour to explore Clearwater's hidden gems, their experienced captains know the best places for swimming, shelling, dolphin watching, and partying. Just bring your loved ones, drinks, and snacks, and they'll take care of the rest. Enjoy a breathtaking sunset from the water, swimming at sandbars, visiting islands, and shelling at Caladesi State Park. They offer daily 4 and 8-hour private tours for both small and large groups, making them the perfect choice for celebrations or vacations. With a focus on fun and safety, Clearwater Party Boats ensure an unforgettable experience for all their guests.

Schooner Clearwater is a premier travel agency located at 25 Causeway Boulevard in Clearwater, Florida. Specializing in unique and unforgettable travel experiences, Schooner Clearwater offers a wide range of services to help you plan the perfect getaway. Whether you're looking for a relaxing beach vacation, an adventurous cruise, or a cultural tour, our knowledgeable staff is dedicated to providing top-notch customer service and personalized travel recommendations. Let Schooner Clearwater be your guide to the world's most exciting destinations.

Welcome to Clearwater Beach PaddleBoard & Rental, your ultimate destination for all your beach adventure needs in Clearwater, Florida! Conveniently located at 439 Poinsettia Avenue, just next to the Clearwater Beach Visitor Center, we offer a wide range of rentals and gear to enhance your coastal experience. Whether you're looking to explore the stunning waters on a paddleboard, kayak through the serene harbor, or simply cruise along the beachfront on a bicycle, we have everything you need. Our extensive rental inventory includes paddleboards, kayaks, bikes, fishing poles, beach chairs, umbrellas, and much more. We even offer electric bicycles for those looking to add a bit of excitement to their ride.

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!

Shell Island Beach is a stunning natural park located in Panama City, Florida, United States. This picturesque beach is a haven for nature lovers and beach enthusiasts alike. With its pristine white sand, crystal clear waters, and abundance of seashells, Shell Island Beach offers a tranquil escape from the hustle and bustle of everyday life. Visitors can relax on the beach, go for a swim, or explore the island's diverse wildlife and marine life. Whether you're looking for a peaceful retreat or an adventurous day out, Shell Island Beach has something for everyone.

Island House Resort Hotel, located at 17103 Gulf Boulevard in North Redington Beach, Florida, offers spacious and well-appointed guest rooms for an ideal stay. Conveniently located near top tourist attractions in St. Pete Beach, Florida, the hotel provides attentive service and top on-site amenities to enhance your North Redington Beach getaway. The hotel invites guests to enjoy the beautiful surroundings of North Redington Beach, nestled between St. Pete Beach and Clearwater Beach. With easy access to the Gulf of Mexico, guests can soak up the sun and explore museums, botanical gardens, aquariums, and more in the area.

Picnic Island Disc Golf Course is a hidden gem located at 7409 Picnic Island Boulevard in Tampa, Florida. This spacious park is the perfect destination for families looking to relax or have a picnic. Children can enjoy the sandy playground and beach, while adults can take advantage of the sand volleyball court and disc golf course. The park also features a dog beach near the boat ramp and pier. With a beautiful white sand beach, tranquil waters, and breathtaking sunsets, Picnic Island offers a beach experience that rivals those in Clearwater. The park's extra-wide concrete boat ramp is open 24 hours and includes a fishing pier and restroom facilities. Spacious shelters equipped with picnic tables, grills, and trash receptacles are available for outdoor events, with a large corporate event shelter also on site.

Holiday Inn Express & Suites Clearwater North/Dunedin, an IHG Hotel, is a comfortable and convenient lodging option located at 975 Broadway in Dunedin, Florida, United States. This modern hotel offers a range of amenities including free Wi-Fi, a complimentary breakfast buffet, an outdoor pool, a fitness center, and spacious rooms and suites with comfortable beds and modern furnishings. Situated in a prime location near Clearwater Beach and Honeymoon Island State Park, guests can enjoy easy access to the area's top attractions, restaurants, and shops. Whether you're traveling for business or leisure, Holiday Inn Express & Suites Clearwater North/Dunedin is the perfect choice for a relaxing and enjoyable stay.

Welcome to Clearwater Beach Scooter and Bike Rentals, your go-to destination for fun and convenient transportation in beautiful Clearwater Beach, Florida! Located at 619 South Gulfview Boulevard, behind Shephard’s Beach Resort, we offer a fantastic selection of rental options to suit your beachside adventures. Choose from our new Kymco scooters, 3-Speed Beach Cruiser bikes, or stylish golf carts equipped with Bluetooth audio and LED lights. Our quick and easy rental process ensures you spend more time enjoying the sights and sounds of Clearwater Beach. Whether you're cruising along the coast on a scooter, exploring town on a bike, or making a statement with one of our golf carts, we have flexible rental options available by the hour, day, or week.

Clearwater Beach Marriott Suites on Sand Key is a luxurious lodging option situated at 1201 Gulf Boulevard in Clearwater, Florida. This stunning beachfront property offers spacious suites with modern amenities, breathtaking views of the Gulf of Mexico, and easy access to the pristine white sand beaches of Sand Key. Guests can enjoy a range of on-site facilities including a tropical outdoor pool, fitness center, and delicious dining options. With its prime location and top-notch services, Clearwater Beach Marriott Suites on Sand Key is the perfect destination for a relaxing beach getaway.

Welcome to Crooked Island Beach, a hidden gem nestled in the heart of Panama City, Florida. Located at the address Panama City, Florida 32403, this pristine natural feature offers a tranquil escape from the hustle and bustle of everyday life. Known for its unspoiled beauty, Crooked Island Beach is the perfect destination for nature lovers, beachgoers, and adventure seekers alike. With its crystal-clear waters, soft white sands, and breathtaking views, Crooked Island Beach provides a serene backdrop for a day of relaxation or exploration. Whether you're looking to sunbathe, enjoy a leisurely swim, or indulge in a peaceful stroll along the shoreline, this beach has something for everyone. The surrounding natural landscape also offers opportunities for birdwatching, fishing, and photography, making it a favorite spot for outdoor enthusiasts.

SeaBreeze Island Grill is a tropical paradise located at 17855 Gulf Boulevard in Redington Shores, Florida. This waterfront restaurant offers a culinary experience that will transport you to the islands with every bite and sip. From mouthwatering seafood dishes to refreshing tropical cocktails, you'll feel like you're on vacation. Join us every third Friday for a special Luau event featuring free roasted pig samples, Waikiki dancers, games, and a Limbo contest. Indulge in dishes like jerk-spiced shrimp, coconut-crusted shrimp, and jerk chicken linguini. Don't miss the grilled salmon with a sweet and tangy glaze over fire-roasted corn salsa.

Clearwater Jetski Tours and Rentals is a travel agency located at 25 Causeway Boulevard in Clearwater, Florida, United States. They offer exciting jet ski tours to Honeymoon Island, Caladesi State Park, and Three Rooker Island where guests can shell, swim, and even catch a glimpse of dolphins. With the largest fleet of jet skis in Clearwater, Florida, visitors can explore the area at their own pace or with experienced guides. Safety is a top priority, and all prices include everything with no hidden fees. Customers rave about their experiences with knowledgeable and friendly guides who ensure a memorable and safe adventure. To operate a wave runner, guests must have a boaters safety license and photo ID if born after 12/31/87. Clearwater Jetski Tours and Rentals also offer a discounted online test to obtain the required license. Book your jet ski tour online today for an unforgettable experience on the waters of Clearwater Beach!

Santa Rosa Island Beach is a pristine park located at 30 State Highway in Destin, Florida, United States. This beautiful beach offers crystal clear waters, soft white sand, and stunning views of the Gulf of Mexico. Visitors can relax on the shore, swim in the ocean, or take a leisurely stroll along the coastline. With its tranquil atmosphere and picturesque surroundings, Santa Rosa Island Beach is the perfect destination for a day of sun, surf, and relaxation.

Located at 325 South Gulfview Boulevard in Clearwater, Florida, The Beachview Inn Clearwater Beach is the perfect destination for those looking to experience the warm sun, white sandy beaches, and soothing gulf breezes of beautiful Clearwater Beach. With the motto of "Rest. Play. Repeat.", the goal of The Beachview is to take relaxation to the next level...sea level. Situated across Beachwalk, guests can easily kick off their flip flops, dig their toes into the sand, and escape from the stresses of everyday life. The Beachview offers breathtaking views of Clearwater Beach during the day, and guests can enjoy poolside firepits at dusk while taking in an unforgettable sunset. Whether guests are seeking romance, relaxation, or family time, The Beachview provides exceptional service, a friendly atmosphere, and modern accommodations to cater to all needs.

301 Island Key is a cozy lodging institution located at 692 Bayway Boulevard in Clearwater, Florida, United States. This charming establishment offers comfortable accommodations for guests looking to relax and enjoy the beautiful surroundings of Clearwater. With its convenient location near the waterfront, guests can easily access the beach and other attractions in the area. Whether you're looking for a weekend getaway or a longer stay, 301 Island Key provides a welcoming atmosphere for all travelers.

Sand Dollar Island Tours Coquina boat ramp is a travel agency located at 1507 Gulf Drive South in Bradenton Beach, Florida. They offer exciting tours to Sand Dollar Island, where visitors can enjoy the beautiful white sandy beaches and crystal clear waters. The Coquina boat ramp provides easy access to the island, making it convenient for tourists to embark on their adventure. With knowledgeable guides and top-notch amenities, Sand Dollar Island Tours ensures a memorable and enjoyable experience for all who visit.

Fins Up Clearwater is a travel agency located at 25 Causeway Boulevard in Clearwater, Florida, United States. Embark on the ultimate coastal adventure with Fins Up Clearwater as they offer a variety of tours to explore the beauty of Clearwater Beach and its surroundings. From exhilarating Sandbar Tours to Dolphin Cruises and Sunset Cruises, Fins Up Clearwater provides unforgettable experiences along Florida's stunning coastline. Experience the Island Sandbar & Dolphin Adventure Tour, where you can enjoy a day of sun-soaked bliss on a secluded island with white sandy shores and crystal-clear waters. Keep an eye out for playful dolphins on the Dolphin Cruises and witness the breathtaking beauty of a Gulf Coast sunset on the Sunset Cruises.

Welcome to Island in the Sun 55 Community, a premier lodging and RV park located in the heart of Clearwater, Florida. Nestled at 100 Hampton Road, our community offers a serene and vibrant environment designed specifically for active adults aged 55 and over. At Island in the Sun, we pride ourselves on providing an exceptional living experience that combines the comforts of home with the excitement of a resort. Our beautifully maintained grounds and well-appointed facilities make it the perfect place to relax, socialize, and enjoy the Florida sunshine. Whether you're staying in our modern lodging accommodations or parking your RV in one of our spacious sites, you'll find everything you need for a comfortable and enjoyable stay.

JolliMons Island is a charming restaurant located at 301 South Belcher Road in Clearwater, Florida. This tropical-themed eatery offers a delightful dining experience inspired by the flavors of the Caribbean. Guests can enjoy a variety of delicious dishes, from fresh seafood to flavorful jerk chicken, all served in a relaxed island atmosphere. Whether you're looking for a casual meal with friends or a romantic dinner for two, JolliMons Island is the perfect destination to satisfy your cravings for tropical cuisine. Come and escape to a culinary paradise at this unique restaurant in the heart of Clearwater.

Luxury Homes by BeachTime Rentals Treasure Island is a premier real estate and travel agency located at 10088 Gulf Boulevard in Treasure Island, Florida. This stunning beach villa offers 4 bedrooms and 4 bathrooms, accommodating up to 14 guests. The property features a private pool, game room with pool table, outdoor kitchen, and balconies with breathtaking views of the Gulf and Intercoastal waterways. The fully equipped kitchen, spacious living areas, and comfortable bedrooms make this vacation home a luxurious retreat for families and groups. Located on Florida's Gulf Coast, Treasure Island offers a laid back atmosphere with easy access to nearby attractions such as John's Pass and St. Pete Beach. Guests can also enjoy the convenience of the Jolley Trolley for exploring the area. Travel insurance is recommended for added peace of mind. Contact Beach Time Rentals for more information and to book your unforgettable beachfront vacation.

Salt Life Island Attitude is a trendy clothing store located at 399 Mandalay Avenue in Clearwater, Florida. Embodying the laid-back and carefree spirit of island life, this store offers a wide selection of beachwear, casual apparel, and accessories that exude a relaxed, beachy vibe. Whether you're looking for the perfect outfit for a day at the beach or simply want to add some coastal flair to your wardrobe, Salt Life Island Attitude has something for everyone. Visit us today and embrace the island attitude!

Patio Palms of Clearwater is a charming lodging institution located at 1295 Cleveland Street in Clearwater, Florida, United States. Nestled in a peaceful and tropical setting, this cozy retreat offers comfortable accommodations and a relaxing atmosphere for guests to enjoy. With its convenient location near popular attractions and amenities, Patio Palms of Clearwater is the perfect choice for travelers seeking a tranquil stay in the Sunshine State. Whether you're visiting for business or pleasure, you'll feel right at home at this welcoming oasis.

Welcome to Clearwater Beach Slingshots, your ultimate destination for an exhilarating ride along the stunning shores of Clearwater Beach! Conveniently located at the beautiful Courtyard by Marriott Clearwater Beach, 455 East Shore Drive, Clearwater, Florida 33767, we offer the only Polaris Slingshots on the beach. Our rentals promise the perfect blend of safety, style, and excitement for your adventure. Rev up your vacation and explore Clearwater Beach like never before in one of our stylish Slingshot rentals. Whether you're seeking the thrill of a motorcycle with the safety of a car or simply want a unique way to see the beach, Clearwater Beach Slingshots is your go-to choice. We provide assistance with planned routes along the breathtaking barrier islands of Clearwater, Indian Rocks, St. Pete, and Pass-A-Grille, or you can chart your own course and explore at your leisure.

Rodeway Inn Clearwater-Dunedin is a cozy and budget-friendly lodging option located in Clearwater, Florida. Situated at 28596 US Highway 19 North, this hotel offers comfortable rooms and convenient amenities for travelers looking to explore the beautiful beaches and attractions of the area. With a prime location near Dunedin and Clearwater Beach, guests can easily access popular destinations such as Honeymoon Island State Park and Caladesi Island State Park. Whether you are in town for a relaxing beach vacation or a business trip, Rodeway Inn Clearwater-Dunedin provides a welcoming and affordable stay for all guests.

Clearwater Vacation Homes is a premier real estate and travel agency located in Treasure Island, Florida. Situated at 8584 West Gulf Boulevard, this institution offers a wide range of luxurious vacation homes for rent in the beautiful Clearwater area. Whether you are looking for a cozy beachfront cottage or a spacious waterfront villa, Clearwater Vacation Homes has the perfect accommodation for your next getaway. With top-notch customer service and a commitment to excellence, this agency is dedicated to providing unforgettable vacation experiences for all guests. Book your dream vacation home with Clearwater Vacation Homes today and make memories that will last a lifetime.