TOP 30 Florida rentals in Longboat Key, Florida

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Shore Longboat Key is a charming waterfront restaurant located at 800 Broadway Street in Longboat Key, Florida. Offering a delightful dining experience with stunning views of the water, this institution specializes in serving delicious seafood and other culinary delights. Guests can enjoy a relaxing meal in a casual yet elegant atmosphere, perfect for both intimate dinners and group gatherings. With a menu featuring fresh, locally sourced ingredients and a variety of delectable dishes, Shore Longboat Key is a must-visit destination for food enthusiasts looking to savor the flavors of the Gulf Coast.

Lagoon Lawn at Longboat Key is a charming lodging establishment located at 201 Gulf of Mexico Drive in Longboat Key, Florida. Nestled in a serene and picturesque setting, this institution offers guests a tranquil escape with stunning views of the lagoon. The lush green lawn creates a peaceful atmosphere, perfect for relaxation and unwinding. With comfortable accommodations and top-notch amenities, Lagoon Lawn at Longboat Key is the ideal destination for a rejuvenating getaway on the beautiful Gulf Coast of Florida.

Siesta Key Watersports is a top-rated tourist attraction and travel agency located at 1536 Stickney Point Road in Sarasota, Florida. With over 28 years of experience in the business, our friendly staff and well-maintained equipment ensure a carefree outing for all our guests. Our highly trained parasail captains work year-round, and we have a professional mechanic on staff to keep all systems in top condition. Our boat rentals allow you to explore the Gulf of Mexico and visit popular beaches like Siesta Key Beach, Lido Beach, Longboat Key, and more. You can also cruise to islands and sandbars in the Intracoastal Waterway or pass by celebrity homes on your way to local hotspots. If you prefer not to drive the boat yourself, we can arrange for a licensed captain to guide you on your chosen trip.

Longboat Key Paddleboard and Kayak is a premier institution located at 4134 Gulf of Mexico Drive in Longboat Key, Florida. Offering kayaking and paddleboarding experiences on the bay, all rentals and tours include top-of-the-line equipment, thorough orientation and instruction, as well as launching and landing assistance at their stunning Sarasota Bay paddling site. Whether you're a beginner or experienced paddler, Longboat Key Paddleboard and Kayak provides everything you need for a memorable and enjoyable adventure on the water.

Rent The Keys is a lodging, real estate, and travel agency located at 3018 Gulf Drive in Holmes Beach, Florida. Start your vacation now by booking Florida Keys luxury vacation rentals through RentTheKeys.com. Discover the value and savings of staying in vacation rental homes or condominiums with amenities such as heated pools, gourmet kitchens, and custom-designed properties on the best beaches in the world. Explore the various keys on the Gulf Coast of Florida, including Siesta Key, Anna Maria Island, Lido Key, Longboat Key, and Casey Key. Experience island living on Anna Maria Island and Siesta Key with miles of white sandy shores and crystal-clear waters. RentTheKeys also offers Sarasota Florida Keys vacation rentals.

Coco Plum of Longboat Key Vacation Home Rental is a real estate and travel agency located at 690 Penfield Street in Longboat Key, Florida, United States. This amenity-packed 2-bedroom, 2-bathroom vacation rental offers a quiet and serene location, a fully equipped kitchen, multiple balconies with lounge furniture, and a patio with hammock swings for ultimate relaxation. Guests can rent a boat or bring their own to park at the on-site canal-front boat dock. Enjoy reading by the pool or sipping a drink on the beach during your month-long getaway. Explore the surrounding area by sea, with attractions such as Cannons Marina, Beer Can Island, and Siesta Key within easy reach. On land, visit Leffis Key Preserve, Portosueno Park, and Robinson Preserve for outdoor adventures. Nearby attractions include the Beach Market at Coquina Beach, the Florida Maritime Museum, and Downtown Sarasota.

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.

Florida Dream Home Team - Coldwell Banker Realty is a premier real estate agency located at 8334 Market Street in Bradenton, Florida, United States. Specializing in properties in the vibrant community of Lakewood Ranch, which is home to over 55,000 residents and 1,841 jobs, our team offers expertise in buying and selling homes in this desirable area. Lakewood Ranch boasts A-rated schools, town centers, golf courses, and the Lakewood Ranch Medical Center, making it an ideal place to live. Additionally, we also serve the beautiful barrier island of Longboat Key, known for its stunning beaches and mangroves. Sarasota, with its unique arts scene and beachy atmosphere, is another area we cover, along with the popular Siesta Key, home to the award-winning Siesta Public Beach. Whether you are looking for a vacation home, investment property, or your dream residence, our team can help you find the perfect property. Visit us today to access full property details and exclusive listings. Prices and inventory are current as of April 6, 2024. To continue your property search, agree to our Terms of Use.

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.

3 Palms by the Beach is a premier beachfront rental agency located on the stunning Longboat Key in Florida. Situated at 4325 Gulf of Mexico Drive, this institution offers luxurious vacation rentals with breathtaking views of the Gulf of Mexico. Whether you are looking for a romantic getaway, a family vacation, or a solo retreat, 3 Palms by the Beach has the perfect accommodations for you. With top-notch amenities and exceptional customer service, this real estate and travel agency is dedicated to helping you create unforgettable memories by the beach. Experience the beauty and tranquility of Longboat Key with 3 Palms by the Beach.

Longboat Key Luxury is a prestigious real estate agency located on Gulf of Mexico Drive in Longboat Key, Florida. Recognized as the top sales team in the state of Florida with Coldwell Banker in 2022, we are in the top 0.5% for all Coldwell Banker Realtors® worldwide. Led by the Kepecz-Hays Team, we have sold over $173 million in the last two years and five months, with a career sales total of over $2.4 billion. Our extensive network of REALTORS® in European countries has helped us establish a strong presence in the luxury real estate market. Located at 2251 Gulf of Mexico Drive, #204, Longboat Key, FL 34228, our agency specializes in luxury properties in Longboat Key, Lido Key, and Sarasota. We offer premier properties and private viewings for buyers, along with expert marketing strategies to ensure a seamless buying or selling experience. With a focus on waterfront neighborhoods, we provide unparalleled excellence in Florida's elite real estate market.

Kayak Jack's Paddle Sports is a premier destination for kayak and stand-up paddleboard rentals on Anna Maria Island, Longboat Key, and Robinson Preserve. Located at 5501 Marina Drive in Holmes Beach, Florida, this store and travel agency offers a wide range of watercraft for exploring the beautiful waters of the Gulf Coast. Whether you're a beginner looking for a leisurely paddle or an experienced adventurer seeking a thrilling excursion, Kayak Jack's has everything you need for an unforgettable outdoor experience. With top-of-the-line equipment, knowledgeable staff, and convenient location, Kayak Jack's is the perfect choice for your next aquatic adventure.

Ultimate Kayak SRQ located at 8918 Midnight Pass Road in Siesta Key, Florida, offers family-friendly and safe kayak and stand up board rentals and tours in the Sarasota area. With tours in Lido Key, Siesta Key, Longboat Key, and Celery Fields, visitors can explore the beauty of the mangrove tunnels and hidden beaches while spotting dolphins and manatees. The institution provides top-of-the-line paddle boards and equipment for an unforgettable experience. Whether you're looking for a guided tour or a self-guided adventure, Ultimate Kayak SRQ has something for everyone. Their tours are suitable for all ages and skill levels, ensuring a fun and educational experience in Florida's natural ecosystems. Contact them today to book your ultimate kayak adventure!

Cannons Marina Boat Sales & Rentals is a family-owned and operated boat dealership located at 6040 Gulf of Mexico Drive in Longboat Key, Florida. With over 68 years of experience, our boutique-style operation allows us to focus on providing a customized boating solution tailored to your needs and style. We are proud partners with Grady-White Boats, known for their performance, reliability, and quality. Our services include boat and yacht brokerage, new and used boat sales, and the best boat rentals program without high club fees. We also offer Yamaha outboard motors for sale and service. Our certified yacht brokers can help you buy or sell your boat with ease. Whether you're looking to rent a boat for a day, week, or longer, Cannons Marina has you covered. We are the only certified Yamaha Motor Service Center in Sarasota-Manatee, providing reliable service and repairs. Visit us today and let us help you make the most of your Florida boating experience.

Chart House, located at 201 Gulf of Mexico Drive in Longboat Key, Florida, is a top waterfront restaurant offering stunning views of Sarasota Bay. With a relaxing atmosphere both inside the dining room and outside on the terrace, this seafood restaurant is the perfect escape from the daily grind. Enjoy Happy Hour specials daily from 4PM to 6:30PM, as well as early dining hours from 4PM to 6PM. Indulge in delicious seafood specialties with a local twist, or sip on cocktails at the comfortable bar seating. Situated on beautiful Longboat Key, Chart House is a tropical retreat just a short drive away from outdoor destinations like South Lido County Park and Bay Island Park. With boat rentals, bike tracks, and more nearby, this restaurant is the ideal spot for a relaxing getaway. As they reopen their dining rooms, Chart House is committed to ensuring the safety of their guests and looks forward to serving you once again.

Beach Bum Divers is a premier diving school located at 6981 Lois Avenue in Longboat Key, Florida. Our institution offers a variety of courses for divers of all levels, from beginners to advanced. With experienced instructors and top-of-the-line equipment, we provide a safe and enjoyable learning environment for our students. Whether you're looking to get certified or improve your skills, Beach Bum Divers is the perfect place to explore the underwater world. Join us and experience the thrill of diving in the beautiful waters of Florida.

Island Adventure Outfitters is a family-run store and travel agency located at 6844 Gulf of Mexico Drive, Longboat Key, Florida. Our team of expert naturalists and certified paddling instructors are passionate about exploring and educating others about the beauty of our watery world. We offer kayak and paddleboard rentals, as well as award-winning tours around Anna Maria Island, Longboat Key, Lido Key, and Sarasota. Whether you want to kayak with friendly manatees and dolphins, explore Sarasota Bay's mangrove tunnels, or enjoy a spectacular sunset tour, we have the perfect adventure for you. Our Coastal Island Tour, where you can kayak with manatees and dolphins, has been a favorite for the past 10 years. Families love our Lido Key mangrove tunnel tours, which offer well-marked paddling trails through the mangrove forest.

Rolling Waves Beach Cottages is a charming lodging institution located at 6351 Gulf of Mexico Drive in Longboat Key, Florida, United States. Situated right on the beautiful shores of the Gulf of Mexico, this cozy retreat offers guests a peaceful and relaxing beachfront experience. The cottages are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy stunning ocean views, relax on the private beach, or take a dip in the crystal-clear waters. With its serene atmosphere and convenient location, Rolling Waves Beach Cottages is the perfect destination for a memorable beach getaway.

Cannons By the Sea Cottages is a charming lodging establishment located at 6051 Gulf of Mexico Drive in Longboat Key, Florida. Nestled along the beautiful Gulf Coast, this institution offers cozy and well-appointed cottages for rent, perfect for a relaxing beach getaway. As both a real estate and travel agency, Cannons By the Sea Cottages also assists guests in finding their dream vacation home or planning their next adventure in the Sunshine State. With its stunning location and personalized service, Cannons By the Sea Cottages is the ideal destination for those seeking a peaceful and idyllic escape.

Arbors By the Sea is a charming lodging institution located at 5441 Gulf of Mexico Drive in Longboat Key, Florida. Nestled in a picturesque coastal setting, this tranquil retreat offers guests a peaceful escape from the hustle and bustle of everyday life. With its cozy accommodations, stunning views of the Gulf of Mexico, and convenient location near the beach, Arbors By the Sea is the perfect destination for those seeking relaxation and rejuvenation. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, this hidden gem on the shores of Florida is sure to provide an unforgettable experience.

Bayfront Park Recreation Center is a vibrant and bustling park located at 4052 Gulf of Mexico Drive in Longboat Key, Florida. This institution offers a wide range of recreational activities and facilities for visitors of all ages to enjoy. From tennis courts and basketball courts to playgrounds and picnic areas, there is something for everyone at Bayfront Park. The beautiful waterfront location provides stunning views of the Gulf of Mexico, making it the perfect spot for a relaxing day outdoors. Whether you're looking to play sports, have a family picnic, or simply enjoy the natural beauty of the area, Bayfront Park Recreation Center is the ideal destination for outdoor fun in Longboat Key.

Captain Fin's Sightseeing and Boat Tours is a popular tourist attraction and travel agency located at 1325 Gulf Drive South in Bradenton Beach, Florida, United States. Specializing in sunset cruises, dolphin excursions, sandbar trips, shelling adventures, and Egmont Key charters, Captain Fin's offers a unique way to explore the beautiful intercoastal waterways of Anna Maria, Longboat Key, and Sarasota Bay. With over 45 years of experience on the waters of Anna Maria Island and Tampa Bay, Captain Fin's ensures a memorable and enjoyable experience for all guests. Don't miss the opportunity to relax and watch the stunning sunset while sipping on your favorite beverage, or to collect shells along the secluded beaches of Egmont Key. Book your sightseeing and boat tour with Captain Fin's today for an unforgettable adventure on the waters of Florida's Gulf Coast.

BouYah Watersports at Zota Beach Resort offers an exciting array of water activities and rentals for guests to enjoy on the beautiful Gulf of Mexico. Located at 4711 Gulf of Mexico Drive in Longboat Key, Florida, this premier watersports institution provides top-of-the-line equipment and expert instruction for activities such as jet skiing, paddleboarding, kayaking, and more. Whether you're seeking thrilling adventures or a relaxing day on the water, BouYah Watersports has something for everyone. Come experience the best of Florida's waterways at Zota Beach Resort.

Marys Maid Cleaning Corp, located at 6350 Gulf of Mexico Drive, Longboat Key, Florida, is dedicated to providing top-quality cleaning services to make your home feel like a vacation retreat. Our goal is to free you from the stress of cleaning so you can enjoy your time doing what you love. We offer customizable cleaning packages to meet your specific needs and ensure your home is clean and safe. Whether you need a Deep Cleaning Service for a special occasion or just want to maintain a tidy home, our experienced team uses non-toxic products to leave your space spotless and disinfected. Our Departure Cleaning Service is perfect for property owners who rent out their homes, ensuring a thorough clean before your next guest arrives.

Turtle Crawl Inn Resort is a beachfront paradise located at 4235 Gulf of Mexico Drive, Longboat Key, Florida. Offering easy living on the Gulf Coast, this resort features vacation beach condos near Sarasota, Florida. With a variety of room styles including accommodations at The Towers, The Gardens, and The Villas, guests can enjoy plush island luxury and quiet pleasures that cater to all personalities. The resort has 20 units directly facing the beautiful Gulf of Mexico, all with one bedroom, one bathroom, and a studio apartment style living area with a balcony overlooking the beach. Most units include a sleeper sofa and can accommodate up to 6 people. Guests can enjoy the heated pool, barbecue area, putting green, shuffleboard area, and easy access to the beach. The resort offers clean and comfortable rental condominiums and villas with fully equipped kitchens. Visitors can partake in activities such as shelling, biking, fishing, watersports, and dining, or simply relax on the white sand beaches and enjoy the warm Sarasota sun. With excellent views of the water and spectacular sunsets, Turtle Crawl Inn Resort is the perfect choice for a Longboat Key vacation. Previous guests have praised the resort for its friendly staff, peaceful atmosphere, and private beach access, making it a top choice for a relaxing getaway.

The Diplomat Beach Resort is a luxurious lodging destination located at 3155 Gulf of Mexico Drive in Longboat Key, Florida, United States. This prestigious resort offers unparalleled comfort and service, making it the perfect retreat for those seeking a relaxing getaway. With stunning views of the Gulf of Mexico and a range of amenities including a pool, spa, and fine dining options, guests are sure to have a memorable stay. Whether you're looking for a weekend escape or a long-term rental, The Diplomat Beach Resort is the ideal choice for your next vacation or real estate investment.

Beach Castle Resort is a luxurious beachfront property located at 5310 Gulf of Mexico Drive in Longboat Key, Florida. As a premier lodging destination, this resort offers guests a tranquil and relaxing atmosphere with stunning views of the Gulf of Mexico. With a range of accommodations to choose from, including spacious suites and private villas, guests can enjoy a comfortable stay with all the amenities they need. In addition to providing lodging, Beach Castle Resort also operates as a real estate agency, helping individuals find their dream beachfront property in the area. The resort also offers travel agency services, assisting guests with booking tours, excursions, and transportation during their stay. Whether you're looking for a vacation rental, a new home, or assistance with planning your trip, Beach Castle Resort has everything you need for a memorable stay in beautiful Longboat Key.

Four Winds Beach Resort is a charming lodging establishment located on the stunning Gulf of Mexico Drive in Longboat Key, Florida. This beachfront resort offers guests a serene and tranquil escape with breathtaking views of the ocean. The resort features comfortable accommodations, a sparkling outdoor pool, direct beach access, and a variety of amenities to ensure a relaxing stay. Whether you're looking to unwind by the water or explore the nearby attractions, Four Winds Beach Resort is the perfect destination for your next getaway.

RVA Resort Vacations is a premier lodging, real estate, and travel agency located at 4030 Gulf of Mexico Drive in beautiful Longboat Key, Florida. With a focus on luxury accommodations and top-notch customer service, RVA Resort Vacations offers an array of vacation rental options, real estate opportunities, and travel services to suit every need. Whether you're looking for a relaxing beachfront retreat or a prime investment property, RVA Resort Vacations has you covered. Book your next vacation or find your dream home with RVA Resort Vacations today!

The Starfish Motel is a cozy and charming lodging establishment located at 2813 Gulf of Mexico Drive in Longboat Key, Florida, United States. Situated just steps away from the beautiful Gulf of Mexico, this quaint motel offers comfortable accommodations for travelers looking to relax and unwind. The Starfish Motel provides a peaceful and serene atmosphere, perfect for a beach getaway or a weekend retreat. With its convenient location and friendly staff, guests can enjoy a memorable stay at this delightful seaside retreat.