TOP 10 Beach vacation rentals in Longboat Key, Florida

Welcome to Public Beach Access on Longboat Key Discover the serene beauty of Longboat Key's beaches with convenient public access points along Gulf of Mexico Drive. Located at 4795 Gulf of Mexico Drive, Longboat Key, Florida 34228, our park offers a tranquil escape to the Gulf of Mexico's stunning shoreline.

Welcome to Longboat Key Little Beach, a hidden gem nestled along the stunning shores of Longboat Key, Florida. Located at 201 Florida 789, our charming beach offers a serene escape for tourists and locals alike. Known for its pristine white sands and crystal-clear waters, Longboat Key Little Beach is the perfect destination for those seeking tranquility and natural beauty. Whether you're looking to relax under the warm Florida sun, take a leisurely stroll along the shore, or enjoy a picturesque picnic with loved ones, our beach provides the ideal setting. The gentle waves and calm atmosphere make it a favorite spot for families and beachgoers of all ages.

Welcome to Banyan Beach Estates, your premier real estate agency located at 6917 Longboat Drive South, Longboat Key, Florida. Nestled in the picturesque surroundings of Longboat Key, we specialize in offering exquisite beachfront properties and luxurious estates that capture the essence of coastal living. Our dedicated team of experienced real estate professionals is committed to providing personalized service and expert guidance, ensuring that your property buying or selling experience is seamless and rewarding. Whether you are searching for your dream home, a vacation getaway, or an investment opportunity, Banyan Beach Estates is here to help you navigate the vibrant real estate market of Longboat Key. Discover the tranquil beauty and unparalleled lifestyle that our exceptional properties have to offer. Visit us today and let us turn your real estate dreams into reality.

Welcome to White Sands of Longboat, your perfect tropical getaway nestled in the heart of Longboat Key, Florida. Located at 5114 Gulf of Mexico Drive, our charming lodging offers a serene escape just steps away from the pristine beaches and turquoise waters of the Gulf of Mexico. At White Sands of Longboat, we pride ourselves on providing a tranquil and comfortable stay for every guest. Our well-appointed accommodations range from cozy rooms to spacious suites, each designed to offer a relaxing retreat with all the modern amenities you need. Enjoy the warm Florida sun as you lounge by our sparkling pool, or take a leisurely stroll along the powdery white sands just moments from your door.

Welcome to Michael Saunders & Company – Longboat Key Real Estate Agents, your premier destination for exceptional real estate services in the beautiful Longboat Key, Florida. Located in the heart of this stunning coastal paradise, our dedicated team of experienced real estate professionals is committed to helping you find your dream home or investment property in this sought-after location. At Michael Saunders & Company, we pride ourselves on our deep local knowledge and personalized service, ensuring that every client receives the attention and expertise they deserve. Whether you're looking to buy, sell, or invest, our agents are here to guide you through the process with integrity, professionalism, and a keen understanding of the Longboat Key market.

The Sandpiper Inn is a charming lodging located at 5451 Gulf of Mexico Drive in Longboat Key, Florida. This cozy inn offers a peaceful retreat for guests looking to relax and unwind in a serene beachfront setting. With comfortable accommodations and a friendly staff, the Sandpiper Inn provides a home away from home for travelers seeking a tranquil getaway. Whether you're looking to soak up the sun on the nearby beach or explore the local attractions, the Sandpiper Inn is the perfect place to stay during your visit to Florida.

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.

Outrigger Resort by RVA is a charming lodging establishment located at 5155 Gulf of Mexico Drive in Longboat Key, Florida, United States. This resort offers a peaceful and relaxing atmosphere, perfect for a getaway by the beach. Guests can enjoy spacious accommodations, beautiful ocean views, and a range of amenities including a pool, tennis courts, and easy access to the beach. With friendly staff and a convenient location, Outrigger Resort by RVA is the ideal destination for a memorable vacation in Florida.

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.

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 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.

Little Gull Cottages is a charming real estate and travel agency located at 5330 Gulf of Mexico Drive in Longboat Key, Florida. Our cozy cottages offer a perfect retreat for those looking to escape the hustle and bustle of everyday life. With stunning views of the Gulf of Mexico, our properties provide a peaceful and serene atmosphere for guests to relax and unwind. Whether you're looking for a weekend getaway or a longer stay, Little Gull Cottages is the perfect destination for your next vacation. Contact us today to book your stay and experience the beauty of Longboat Key.

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.

Coldwell Banker Realty is a premier real estate agency located at 100 North Tamiami Trail in Sarasota, Florida. Our office is conveniently situated near the Ritz and Westin, making it easily accessible for all of Sarasota. With over 150 agents, we have a strong customer service reputation and make a significant impact on the real estate market in Sarasota and Manatee Counties. Our office serves a wide range of areas including Sarasota, Bradenton, Bradenton Beach, Lakewood Ranch, Longboat Key, Siesta Key, Venice, Nokomis, Osprey, Anna Maria, and Holmes Beach. We offer a variety of properties including luxury homes, condominiums, new construction, resales, commercial properties, condo-hotels, and fractional ownership. Our experienced agents have received national recognition for their dedication and production.

LaPlaya Condominiums is a luxurious beachfront property located at 4425 Gulf of Mexico Drive in Longboat Key, Florida. This stunning complex offers a range of beautifully appointed condominiums for sale or rent, perfect for those seeking a tropical getaway or a permanent residence in paradise. With pristine white sand beaches just steps away and breathtaking views of the Gulf of Mexico, LaPlaya Condominiums is the perfect destination for those looking to relax and unwind in style. Whether you're looking for a vacation rental or a new home, LaPlaya Condominiums has something for everyone. Contact us today to learn more about this exclusive property and start living the beachfront lifestyle you've always dreamed of.

SURFIT USA-Kayaks, Paddleboards & Surf is a travel agency located at 190 Taft Drive in Sarasota, Florida. They offer exceptional kayak and stand up paddleboard eco-tours and rental equipment in the Sarasota area. Deliveries are available to Lido Key, Siesta Key, and Longboat Key, making it convenient for visitors to explore the beautiful waters of Florida. One of the highlights of their tours is paddling through mangrove tunnels to reach secluded beaches only accessible by boat, providing a unique and peaceful experience. With a guarantee to see dolphins or manatees on tours from April to September, guests are sure to have an unforgettable encounter with local wildlife. Whether you're a beginner looking to try surfing or an experienced paddler seeking new adventures, SURFIT USA has something for everyone. Their knowledgeable guides, led by Aaron, ensure a safe and enjoyable experience for all guests. With years of experience and a passion for sharing the beauty of Sarasota, SURFIT USA-Kayaks, Paddleboards & Surf is the perfect choice for exploring the waters of Florida.

AMI Escapes Boat Tours is located at 6398 Marina Way in Holmes Beach, Florida. It is Anna Maria Island's most popular adventure boat tour, offering private and all-inclusive experiences customized for each group. Guests have the opportunity to visit secluded islands, beaches, and sandbars such as Egmont Key, Passage Key, Jewfish Key, and Beer Can Island. The tours include amenities such as paddle boards, snorkeling gear, fishing poles, and underwater scooters, with no set schedule so guests can enjoy the experience for as long as they desire. In addition to island hopping, the tours also offer stops at local restaurants and opportunities for swimming, snorkeling, and paddle boarding. The institution also offers dolphin tours, snorkeling trips with underwater scooters, and sunset cruises with a premium Bluetooth sound system. With comfortable boats, complimentary water and soft drinks, and the option to bring adult beverages on board, AMI Escapes Boat Tours provides a luxurious and customizable boating experience for visitors to Anna Maria Island, Longboat Key, and Bradenton Beach.

GulfCart Fishing Charters, located in Cortez, Florida, is a top tourist attraction and travel agency offering private fishing charters in the Anna Maria Island, Bradenton, Holmes Beach, Longboat Key, and Cortez Beach areas. Captain Eric Chaignet, with over twenty years of experience fishing the local waters, provides a first-hand perspective on where the fish are biting. Anglers can expect to catch a variety of fish such as Snapper, Grouper, Shark, Redfish, Mackerel, Tarpon, Snook, and Trout on their inshore and offshore fishing excursions. Customers rave about the 5 star experience with GulfCart Charters, praising Captain Eric's knowledge and expertise. Whether it's your first time fishing or you're a seasoned angler, Captain Eric ensures a fun-filled day on the water. With access to some of the most bountiful fishing destinations in Holmes Beach and Cortez Beach, GulfCart Charters promises an unforgettable fishing experience.

Welcome to Twin Shores Inc, your serene getaway on the picturesque Longboat Key in Florida. Nestled at 3740 Gulf of Mexico Drive, our RV park offers a perfect blend of comfort and natural beauty, making it an ideal destination for travelers seeking relaxation and adventure. Surrounded by the stunning Gulf of Mexico, our location provides easy access to pristine beaches, breathtaking sunsets, and a tranquil atmosphere. At Twin Shores Inc, we pride ourselves on offering top-notch amenities and services to ensure your stay is as comfortable as possible. Our well-maintained RV sites are equipped with modern conveniences, catering to both short-term vacationers and long-term residents. Whether you are a solo traveler, a couple, or a family, our friendly staff is dedicated to making your experience memorable.

Welcome to the Gulf of Mexico Dr/5200 Block (White Sands) Transit Station, conveniently located in the picturesque town of Longboat Key, Florida. Nestled along the stunning Gulf Coast, this transit station serves as a vital hub for locals and visitors alike, providing easy access to the beautiful white sand beaches and the vibrant community of Longboat Key. Whether you're commuting to work, exploring the island, or simply enjoying a day by the ocean, our well-maintained station offers a seamless and efficient transportation experience. With its strategic location and user-friendly services, the Gulf of Mexico Dr/5200 Block (White Sands) Transit Station is your gateway to the best that Longboat Key has to offer.

Welcome to AMI Discovery Charters, your ultimate gateway to exploring the stunning waters and hidden gems of Anna Maria Island and beyond. Located at 1507 Gulf Drive South, Bradenton Beach, Florida, our charters offer an unforgettable experience for tourists and locals alike. Led by Captain Max Huber, a Florida native with a lifelong passion for the sea, our excursions promise adventure, relaxation, and a taste of true Florida charm. Step aboard our brand new 24ft Tahoe Cascade Saltwater Series Luxury Tri-toon, powered by a 175 Suzuki motor, and discover the beauty of the Gulf Coast in style and comfort. With space for up to 20 guests, our vessel is equipped with upgraded upholstery and cushions for ultimate relaxation. We provide underwater scooters, paddle boards, and big floating rafts, ensuring fun for the whole family. Plus, enjoy complimentary water and ice with our extra-large cooler for your beverages and snacks.

Welcome to The O'Steen Group, Inc. - Your Trusted Property Partner Located at 6680 Cortez Road West, Bradenton, Florida, The O'Steen Group, Inc. is a family-owned and operated real estate brokerage and property asset management company, proudly serving the community since 2007. We specialize in finance, real estate, and travel services, catering to the unique needs of our clients with a personal touch.