TOP 30 Island vacation deals in Florida

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Anna Maria Island Getaway is a premier real estate and travel agency located in Bradenton Beach, Florida. Our dedicated team is committed to helping you find the perfect getaway on the beautiful Anna Maria Island. Whether you're looking for a beachfront vacation rental, a cozy cottage, or a luxurious villa, we have a wide selection of properties to choose from. Our experienced staff is here to assist you every step of the way, from booking your accommodation to planning your itinerary. Come experience the beauty and tranquility of Anna Maria Island with us at Anna Maria Island Getaway.

Anchor Down Real Estate & Rentals on Anna Maria Island offers top Bradenton & Anna Maria Island vacation rentals. Located at 9801 Gulf Drive in Anna Maria, Florida, this institution serves as a lodging, real estate, and travel agency. With a "No Worry Guest Guarantee" from reservation to check-out, Anchor Down Vacation Rentals provides the finest homes on the Florida Gulf Coast. Guests can enjoy spacious accommodations, beautiful outdoor areas, and excellent customer service. Whether you're looking for a family gathering, a romantic getaway, or a relaxing vacation, Anchor Down Vacation Rentals has the perfect property for you. Book today and experience the beauty of Anna Maria Island with Anchor Down!

Reunion Vacation Homes is a lodging, real estate, and travel agency located at 7531 Osceola Polk Line Road in Davenport, Florida, United States. Specializing in bringing friends and family together in Orlando Vacation Home Rentals and Anna Maria Island Rentals, Reunion Vacation Homes offers a wide range of vacation rentals in select Orlando area resorts close to Disney® such as Reunion Resort, The Retreat at Champions Gate, Windsor at Westside, and more. With options ranging from 2-3 bedroom condos to 10-14 bedroom luxury villas, there is something for everyone. Whether you're looking for top villa rentals near Disney World® in Kissimmee & Davenport, or luxury mansions in Reunion Resort, Reunion Vacation Homes has you covered. With over 300 luxury villas and condos to choose from, guests can enjoy amenities such as private pools, golf course views, and proximity to major attractions.

Island Echos in Fort Walton Beach by Vacasa is a lodging, real estate, and travel agency located at 676 Santa Rosa Boulevard in Fort Walton Beach, Florida, United States. This institution offers vacation rentals for every type of getaway, with 64 rentals equipped with internet access for staying connected during your stay. The professional housekeeping team at Island Echos ensures that each rental is thoroughly cleaned and stocked with amenities for a stress-free arrival. Choose Island Echos - Fort Walton Beach for your next vacation and enjoy a relaxing and comfortable stay.

The Gulf on Okaloosa Island is a unique institution located in Fort Walton Beach, Florida. This establishment stands out with its trademark design elements of shipping containers, reclaimed materials, and a chic yet casual ambiance. The focus on local ingredients ensures that each dish on the seasonal menu is fresh and flavorful. The bar and music selection are carefully curated to enhance the overall experience, while the friendly staff creates a welcoming atmosphere for every visitor. Whether you're looking for a bayfront hideaway for a gathering with friends or a romantic evening with a loved one, The Gulf on Okaloosa Island is the perfect destination. With a rotating menu that changes with the seasons, you can always expect to enjoy the freshest meals in the area. Visit The Gulf on Okaloosa Island for a memorable dining experience that combines great food, music, and hospitality.

Island Outpost is a charming establishment located at 14231 West Ozello Trail in Crystal River, Florida. This unique institution offers a variety of services including a bar, restaurant, gas station, and food options. Whether you're looking for a delicious meal, a refreshing drink, or a pit stop for fuel, Island Outpost has you covered. The laid-back atmosphere and friendly staff make it a perfect spot to relax and recharge while exploring the beautiful surroundings of Crystal River. Visit Island Outpost for a true taste of Florida hospitality.

Coney Island Crystal River is a popular food institution located in Crystal River, Florida. Situated at 674 Northeast 5th Street, this restaurant specializes in serving delicious John Morrell all Meat Hot Dogs. Customers can choose from both short and foot long hot dogs, all cooked to perfection with steam. The menu at Coney Island Crystal River offers a variety of options, including their famous Coney Sauce - a meat sauce with no beans, and homemade chili with beans. In addition to hot dogs, the restaurant also serves specialty hot dogs, corn dogs, and a selection of sandwiches.

Island Wing Company - Rolling Oaks is a lively bar and restaurant located at 3267 Rolling Oaks Boulevard in Kissimmee, Florida. You don't need a passport to experience the delicious food and drinks at this establishment. From crispy chicken wings to juicy burgers, there is something for everyone on the extensive menu. Choose from a large selection of draft beers, frozen drinks, and cocktails to pair with your meal. Whether you're watching the game, enjoying live music, or catching up with loved ones, Island Wing Company is the perfect spot to relax and have a good time. Visit an Island Wing Company location near you or while on vacation to experience why it's always a little better on the Island. And if you've ever dreamed of owning your own island, consider joining the Island Wing Co. family as they continue to expand their locations.

Island Ocean Star is a popular food establishment located at 902 South Bay Boulevard in Anna Maria, Florida, United States. Specializing in Japanese cuisine, Island Ocean Star offers a wide variety of delicious dishes that have been expertly crafted to provide a delightful culinary experience. Whether you're in the mood for sushi, sashimi, or stir-fried noodles, Island Ocean Star has something for everyone. With a seamless ordering process through Beyond Menu, you can easily enjoy your favorite meals through pickup or delivery. Visit Island Ocean Star today and treat yourself to a taste of Japan right here in Anna Maria.

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.

Island Crew is a vibrant and lively restaurant located at 2210 East Hillsborough Avenue in Tampa, Florida. Specializing in delicious Caribbean cuisine, this institution offers a unique dining experience with a tropical twist. From flavorful jerk chicken to savory seafood dishes, Island Crew aims to transport diners to the sunny shores of the Caribbean with every bite. With a welcoming atmosphere and friendly staff, this restaurant is the perfect destination for those looking to escape the ordinary and indulge in a taste of island paradise.

Island Time is a vibrant and lively bar, food, and restaurant located at 937 East Gulf Drive in Sanibel, Florida. With its laid-back island atmosphere and delicious menu offerings, it is the perfect place to unwind and enjoy a taste of tropical paradise. Whether you're looking for a refreshing cocktail, a satisfying meal, or just a relaxing spot to soak up the sun, Island Time has something for everyone. Come experience the true essence of island living at this must-visit establishment in the heart of Sanibel.

Island House is a popular bar, cafe, and restaurant located at 3801 Bonita Beach Road Southwest in Bonita Springs, Florida. Known for its delicious food and great atmosphere, Island House offers a variety of menu options including roasted prime rib, pizza, hot dogs, and cocktails. The institution also hosts live music events on the patio on select nights, featuring talented bands like TIDE UP BAND, LIMITED EDITION BAND, and more. In addition to the entertainment, Island House also offers trivia nights, sports packages, and welcomes private events. Customers rave about the excellent service, friendly staff, and tasty food, making Island House a must-visit spot in Bonita Springs. Whether you're looking for a fun night out with live music or a relaxing meal with friends, Island House has something for everyone.

Island Wing Company - UCF is a vibrant bar and restaurant located at 4100 North Alafaya Trail in Orlando, Florida, United States. Step into our tropical oasis where you can enjoy delicious food, refreshing drinks, and a lively atmosphere with friends and family. No need for a passport to experience the best in wings, burgers, and more from our extensive menu. Choose from a variety of draft beers, frozen drinks, and cocktails to complement your meal. Whether you're watching the game, listening to live music, or catching up with loved ones, Island Wing Company is the perfect spot to unwind and enjoy Island Time. With locations nationwide, you can always find an Island close to you or on your next vacation. Interested in owning your own island? Island Wing Company is rapidly expanding, so learn more about franchise opportunities today. Come see why everything is a little better on the Island!

Black's Island is a luxurious lodging institution located at 2049 Florida 30A, Port St. Joe, Florida, United States. Situated in the heart of St. Joseph Bay, this private island getaway is perfect for anglers and outdoor enthusiasts seeking seclusion and natural beauty. Accessible only by boat, seaplane, or helicopter, guests can enjoy the pristine waters and serene surroundings of this exclusive retreat. With accommodations in private vacation homes, a clubhouse, cabana, pool, sundecks, and various water activities available, Black's Island is the ideal destination for families, friends, corporate retreats, and more. Guests can also explore the mainland with a short trip to the historic village for shopping, dining, and entertainment.

Alvin's Island #2 in Panama City Beach is a popular clothing store and department store located at 9401 Thomas Drive. This store offers a wide range of trendy clothing, beachwear, accessories, and souvenirs for visitors and locals alike. With its convenient location in the heart of Panama City Beach, Alvin's Island #2 is a must-visit destination for those looking for stylish and affordable fashion options. Come explore the latest fashion trends and find the perfect outfit for your next beach adventure at Alvin's Island #2.

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.

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.

The Retreat at Anna Maria Island Inn is a charming lodging establishment located at 2305 Gulf Drive North in Bradenton Beach, Florida. Situated on the beautiful Anna Maria Island, this inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With cozy accommodations, stunning ocean views, and a convenient location near the beach, shops, and restaurants, The Retreat is the perfect destination for a weekend getaway or extended vacation. Whether you're looking to unwind by the pool, explore the island's natural beauty, or simply relax in your comfortable room, The Retreat at Anna Maria Island Inn has everything you need for a memorable stay.

Anna Maria Island Beach Sands is a charming lodging institution located at 601 Gulf Drive North in Bradenton Beach, Florida. Situated right on the beautiful shores of Anna Maria Island, this beachfront property offers guests stunning ocean views and easy access to the pristine sandy beaches. The accommodations are cozy and comfortable, perfect for a relaxing getaway by the sea. With its convenient location, guests can enjoy a variety of water activities, shopping, dining, and exploring the local attractions. Whether you're looking for a romantic escape or a fun family vacation, Anna Maria Island Beach Sands provides the perfect setting for a memorable stay in sunny Florida.

The Islander Resort is a charming lodging establishment situated at 17006 Gulf Boulevard in the beautiful North Redington Beach, Florida. This beachfront resort offers guests a relaxing and peaceful retreat with stunning views of the Gulf of Mexico. The resort features comfortable accommodations, a sparkling swimming pool, a private beach area, and easy access to a variety of local attractions and activities. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, The Islander Resort provides the perfect setting for a memorable stay in sunny Florida.

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.

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.

The Amelia Island Williams House, located at 103 South 9th Street in Fernandina Beach, Florida, is a historic inn offering unparalleled Southern hospitality. With a perfect blend of old-world charm and modern luxury, our award-winning bed and breakfast features ten distinctive guest rooms, each with a private bath. Guests can enjoy a delicious breakfast in a sunlit dining room, explore the charming town of Fernandina Beach, relax on nearby beaches, or unwind in nature preserves. In the evening, unwind with a glass of wine on the veranda. Experience boutique accommodations with Victorian charm on beautiful Amelia Island. Our inn offers vacation packages, romantic getaways, and travel specials to enhance your Florida getaway. Gift certificates are available for any special occasion. Come and experience the rich history and elegant ambience of the Amelia Island Williams House.

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.

Venice Island is a premier hair care institution located at 505 South Tamiami Trail in Venice, Florida. Our skilled and experienced stylists are dedicated to providing top-notch hair care services to our valued clients. From trendy haircuts to vibrant hair coloring, we offer a wide range of services to help you achieve your desired look. Sit back and relax in our modern and comfortable salon while our team works their magic to give you the perfect hairstyle. Come visit us at Venice Island and experience the ultimate hair care experience in the heart of Venice.

The Lido Islander is a premier institution located at 528 South Polk Drive in Sarasota, Florida. As a multi-faceted establishment, it serves as a lodging facility, real estate agency, and travel agency all in one. Whether you are looking for a luxurious place to stay, seeking to invest in property on Lido Key, or planning your next vacation, the Lido Islander offers a one-stop solution for all your needs. With a prime location in the beautiful city of Sarasota, the Lido Islander provides top-notch services and accommodations to ensure a memorable experience for all guests and clients.

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.

Comfort Suites Fernandina Beach at Amelia Island is a cozy and welcoming lodging option located at 2801 Atlantic Avenue in Fernandina Beach, Florida, United States. The hotel offers spacious and comfortable suites, perfect for both leisure and business travelers. Guests can enjoy amenities such as free hot breakfast, a fitness center, and a refreshing outdoor pool. The hotel is conveniently located near the beach, shops, and restaurants, making it a great choice for those looking to explore the beautiful Amelia Island area.

Courtyard by Marriott Amelia Island is a charming lodging destination located at 2700-1 Atlantic Avenue in Fernandina Beach, Florida, United States. This beachfront hotel offers comfortable accommodations and modern amenities for guests looking to relax and unwind. With its convenient location near the beach, guests can enjoy stunning ocean views and easy access to water activities. The hotel also features a fitness center, outdoor pool, and on-site dining options for a convenient and enjoyable stay. Whether visiting for a leisurely vacation or a business trip, Courtyard by Marriott Amelia Island provides a welcoming and comfortable atmosphere for all travelers.