TOP 30 Best island vacations in Clearwater, Florida

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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Welcome to Beso Del Sol Resort! Located at 1420 Bayshore Boulevard in Dunedin, Florida, our waterfront resort offers stunning views of Caladesi and Honeymoon Island on Florida's gulf coast. Whether you're looking for a studio, one- or two-bedroom suite, we have accommodations designed with your comfort and convenience in mind. Situated near Clearwater Beach and Caladesi Island, our resort is the perfect spot for a vacation getaway or destination wedding in delightful Dunedin. On-site, we offer swimming pools, a jacuzzi, Marker 8 tiki bar and grill, complimentary bikes, and the Jolley Trolley to explore the town.

Welcome to Compass Hotel Anna Maria Sound, your personal slice of paradise located at 12324 Manatee Avenue West in Bradenton, Florida. This boutique hotel brings the easy, breezy fun of Margaritaville resorts to the beautiful Anna Maria Island, just a short drive from Sarasota Bradenton International Airport. With 123 gorgeously appointed rooms overlooking a marina and Neal Preserve, this seaside destination is the perfect home base for exploring the Florida Gulf. Enjoy complimentary breakfast buffets, delicious dining, and an attentive team that will make you feel right at home in paradise. Whether you're visiting IMG Academy, Premier Sports Campus, or attending a wedding at The Beach House, Sandbar, or Palma Sola Botanical Gardens, Compass Hotel Anna Maria Sound is the ideal year-round destination.

Provident Oceana Beachfront Suites is a beautiful privately owned all-suite, beachfront, and bayfront boutique condo-resort located at 10091 Gulf Boulevard in Treasure Island, Florida. This family-inspired resort offers the best of both worlds with condo-sized 2 & 3 bedroom suites and resort amenities all under one roof. Conveniently situated on the central-west coast of Florida, just a few miles south of one of America's "Top 7 Beaches," Provident Oceana Beachfront Suites is the perfect destination for a family vacation. With 38 fully equipped suites in two towers, guests can choose between stunning views of the powdery white beach and turquoise waters of the Gulf of Mexico or the peaceful bay and private marina.

Sheraton Sand Key Resort is a luxurious lodging option located at 1160 Gulf Boulevard in Clearwater, Florida. Situated on the beautiful Sand Key barrier island, this resort offers stunning views of the Gulf of Mexico and easy access to the pristine white sand beaches. Guests can enjoy spacious and comfortable accommodations, a variety of dining options, a sparkling outdoor pool, a fitness center, and a range of on-site activities. With its convenient location and top-notch amenities, Sheraton Sand Key Resort is the perfect destination for a relaxing beach getaway in Florida.

Salt Water Suites is a lodging institution located at 16813 Gulf Boulevard in North Redington Beach, Florida, United States. Our uniquely decorated suites are just steps away from the beautiful white sand and serene waters of Florida’s Gulf Coast beaches. Following a complete renovation in late 2022, our accommodations provide all the comforts of home infused with a delightful twist of happiness. Our mission is to make your stay unforgettable, leaving you with lasting memories. With 12 thoughtfully curated suites boasting unique personalities, Salt Water Suites offers the perfect retreat for your vacation getaway. Our prime location in North Redington Beach unveils 35 miles of heavenly coastline, showcasing some of America’s top-rated beaches such as St. Pete’s Beach, Treasure Island, Sand Key, and Clearwater Beach.

Meranova Guest Inn is a hidden gem located at 458 Virginia Lane in Dunedin, Florida. This historic inn offers nine unique apartments and suites for guests to choose from, each with its own charm and character. The inn features a gazebo where guests can relax with a glass of wine and watch the bustling activities of Main Street. The Secret Garden at Meranova Guest Inn provides a peaceful retreat, with a raised vegetable and herb garden for guests to explore. The pool area is the perfect spot to soak up the Florida sun and unwind after a day of exploring the nearby beaches and attractions.

Page Terrace Beachfront Hotel in Treasure Island, Florida offers a relaxing and comfortable stay directly on the beautiful Gulf of Mexico beach. Our family-owned and operated hotel provides modern amenities such as a heated pool, gulf front patio, BBQ grill, and free WiFi. With newly renovated rooms and a commitment to cleanliness, we ensure a pleasant vacation experience for all our guests. Located within walking distance of dining, entertainment, and shopping options in Treasure Island, our hotel is the perfect place to unwind and enjoy the sun, sand, and surf of the Gulf Coast. Whether you prefer to relax on our sundeck or explore the area's attractions, Page Terrace Beachfront Hotel is the ideal choice for your vacation getaway.

Sunset Vistas Beachfront Suites is a premier lodging institution located at 12000 Gulf Boulevard in Treasure Island, Florida, United States. Offering condo-size suites with resort amenities, this property has been awarded a TripAdvisor Certificate of Excellence. With 154 two- and three-bedroom suites, each featuring a spacious living/dining area, full kitchen, and private balcony overlooking the Gulf of Mexico, guests are sure to enjoy their stay. The property also offers a non-refundable advanced purchase option with 20% off for stays of 2 nights or more. Amenities include a resort and children's pool, whirlpool spas, Cafe & Beach Bar, and extended stay options. The large outdoor cafe deck is perfect for family gatherings and events. Nearby dining options in Treasure Island, Tampa, St. Petersburg, and Clearwater provide plenty of choices for guests. Sunset Vistas Beachfront Suites is the ideal destination for a family vacation on the award-winning beaches of southern Florida.

Twins Inn & Apartments, formerly known as Twins Apartments, is a premier lodging destination located at 12520 Gulf Boulevard in Treasure Island, Florida. Situated next to Florida's beautiful white sand beach, between Clearwater Beach and St. Pete Beach, the institution is easily accessible from Tampa International Airport. For over 40 years, Twins has been a popular choice for families seeking a beach vacation experience. The spacious one-bedroom and two-bedroom vacation apartments offer fully equipped kitchens, a heated outdoor swimming pool, and stunning views of the Gulf of Mexico. Each apartment is tastefully decorated with tropical flair and includes amenities such as free Wi-Fi, cable television, and long distance telephone calling.

Voyager Beach Club is a charming lodging and real estate agency located at 11860 Gulf Boulevard in Treasure Island, Florida. The institution is managed by Voyager Beach Club Condo Association, Inc. Guests can enjoy a range of amenities and activities in the St. Pete/Clearwater area, making it the perfect destination for a fun and relaxing vacation. Whether you want to relax on the beach, explore local attractions, or indulge in delicious cuisine, Voyager Beach Club has something for everyone. Book your stay today and experience all that this beautiful area has to offer!

Dockside Condos is a real estate and travel agency located at 445 South Hamden Drive in Clearwater, Florida. Stay with us and experience the beauty of Clearwater Beach, voted the Number 1 Best Beach in the United States by tripadvisor in 2018 and 2019. Our waterfront and beachfront rentals offer a convenient location near popular areas such as St. Petersburg, Tampa, St. Pete Beach, Treasure Island, Indian Shores, and Madeira Beach. Come relax and enjoy all that Clearwater Beach and Tampa Bay have to offer at Dockside Condos.

Coral Cottage IRB is a charming vacation rental located at 202 14th Avenue North in Indian Rocks Beach, Florida. This classic, old Florida beach house features 3 bedrooms and 2 bathrooms, comfortably accommodating up to six guests. The cottage is available for monthly rentals of 30 nights, making it the perfect choice for an extended stay by the beach. Situated just one block off of Gulf Blvd and a short 3-minute walk to the beach, Coral Cottage offers a prime location for a relaxing beach getaway. Indian Rocks Beach is a quiet and less crowded destination, yet it is filled with plenty of activities and amenities within walking distance. Guests can enjoy nearby restaurants, cafes, seafood eateries, grocery markets, and even a playground for families to enjoy.

B&W Management, Inc. is a real estate and travel agency located at 11 Idlewild Street in Clearwater, Florida, United States. Search for vacation rentals by your arrival and departure dates, with arrangements possible for off-season stays. Beach Bobby Rowe offers tips for preparing to stay in vacation rentals on Clearwater Beach. Enjoy your stay on the award-winning Clearwater Beach, ranked as the number one beach in the United States by TripAdvisor in 2018 and 2019, and the number six beach in the world. B&W Management offers beachfront rentals and condominium rentals in Clearwater Beach, Florida, conveniently located near St. Petersburg, Tampa, St. Pete Beach, Treasure Island, Indian Shores, Madeira Beach, and all of Tampa Bay. Book your vacation rental with B&W Management, Inc. for a memorable beach getaway.

John's Pass Condos is a real estate and travel agency located at 12924 Gulf Boulevard in Madeira Beach, Florida. Our condos are ideally situated just steps away from historic John's Pass Village and Boardwalk, offering a wide range of retail outlets, dining options, and activities for the whole family to enjoy. With easy access to nearby beaches like Clearwater Beach and St Pete Beach via the Free Beach Ride Service or Suncoast Beach Trolley, our location is perfect for exploring the Gulf Coast. We offer newly furnished 1, 2, and 3 bedroom beachfront rental condos at various properties including Beach Place, Sandy Shores, Surf Song, Madeira Bay Resort, Villa Madeira, and Madeira Norte. Each condo is designed to provide the ideal vacation environment with amenities such as secure buildings, heated outdoor swimming pools, BBQ grills, and private balconies. Our condos also come fully equipped with cable TV, Wi-Fi, and fully equipped kitchens.

Gulf Coast Luxury Rentals is a premier institution located at 10641 1st Street East, Treasure Island, Florida, United States. We offer a range of services including finance, lodging, real estate agency, and travel agency. With over 15 years of experience in the industry, we are committed to providing exceptional value and excellent customer service to our guests. Our vacation properties in Pinellas County are carefully selected to ensure cleanliness, comfort, and top-notch amenities. Whether you're looking for a cozy cottage or a luxurious getaway, we have something for everyone. From downtown St. Petersburg to Clearwater Beach, there are endless possibilities for attractions and activities to suit every taste.

Sharkey's Glass Bottom Tours is a travel agency located at 4237 Gulf Boulevard in St. Pete Beach, Florida. They offer the original and only Glass Bottom Kayak LED illuminated Fish Feeding Night Tours, providing an unforgettable experience at various locations throughout Florida. The tours take place from sunset to night at 8pm and a full dark night tour at 9:30pm, allowing guests to illuminate the sea-floor while viewing sea-life up close. Visitors can explore the Nature Preserve & Mangrove Tunnels, relax on sandbars, and enjoy snorkeling with the provided equipment. The institution also offers Daytime Island & Mangrove Tunnel Adventures where dolphins and manatees are often spotted. With locations in St. Pete Beach, Clearwater Beach, Sarasota, and West Palm Beach, Sharkey's Water Sports is known for its unique tours that attract sea-life with high powered underwater LED lights. Guests have raved about their experiences, praising the knowledgeable guides, calm waters, and the opportunity to interact with marine life. Whether you're looking for a fun family outing or a romantic date night, Sharkey's Glass Bottom Tours offers a memorable adventure for all ages.

Dolphin Snorkeling Cruise is a travel agency located at 4630 29th Avenue South, Gulfport, Florida, United States. As the official tourism marketing and management organization for St. Pete Clearwater, we offer a unique experience for all ages. Our custom-built single-hull boats provide the perfect opportunity to witness wild dolphins jumping and playing in the warm waters of the Gulf of Mexico. Our tours include a visit to Egmont Key State Park, where you can explore the tropical island with ruins dating back to the 1700s, a working lighthouse, and pristine beaches filled with sea shells. Snorkeling in the clear waters of Egmont Key is a highlight of the trip, perfect for both beginners and experienced swimmers.

A Boat Day is a travel agency located at 401 2nd Street in Indian Rocks Beach, Florida, United States. They offer boat tours and charters in Clearwater Beach, Dunedin, and St. Pete Beach. With experienced boat captains to guide you, you can relax and enjoy the beautiful waterways without having to worry about driving the boat. Choose from a variety of boats, including luxury pontoons, deck boats, and yachts, to explore state park barrier islands, go island hopping, or relax at sand bars. Whether you want a relaxing day on the water or an adventurous experience, A Boat Day has something for everyone. Perfect for birthdays, bachelor and bachelorette parties, family reunions, and corporate events, their private boat parties can accommodate groups of any size. Families with children are welcome, as the boats are family-friendly and provide life jackets for all ages. Whether you're looking for a unique way to celebrate a special occasion or just want to enjoy a day on the water with loved ones, A Boat Day has you covered. TripAdvisor's #1 Boat Tour in Clearwater & Indian Rocks Beach, guests rave about their experiences with friendly and knowledgeable captains who go above and beyond to create unforgettable memories on the water.

A Boat Day is a travel agency located at 198 Seminole Street in Clearwater, Florida, offering unique and unforgettable boating experiences. With friendly and experienced boat captains to guide you, you can enjoy cruising the waterways, island hopping, or anchoring up at sand bars in Clearwater Beach, Dunedin, Indian Rocks Beach, and St. Pete Beach. Choose from a variety of boats, including the luxurious Tahoe Funship, the spacious Hurricane deck boat, the Platinum Funship with a water slide, the Avalon Funship with a Bluetooth sound system, the Buccaneer Funship for a pirate adventure, the Four Winns yacht class deck boat, and more. Sailing charters on the 41-Foot Morgan Out Island Ketch are also available for a relaxing day on the water.