TOP 30 Best Florida gulf coast vacation rentals in Longboat Key, Florida

Welcome to Coastal Key Realty, your premier real estate agency located at 6750 Gulf of Mexico Drive, Longboat Key, Florida. As a leading realtor in the vibrant areas of Anna Maria Island and Longboat Key, Amy Jones and her dedicated team are committed to providing personalized service and expert guidance for all your real estate needs. Whether you are looking to buy, sell, or invest, Coastal Key Realty offers the experience and expertise necessary to navigate the dynamic Florida real estate market. Our website showcases a diverse range of listings, each offering unique opportunities to find your perfect vacation home or permanent residence. From the picturesque community of Cedars Longboat Key to the luxurious Key Royale golf community on Anna Maria Island, we provide comprehensive guides to help you make informed decisions.

Welcome to Longboat Pass Bridge, a charming local landmark and must-visit destination located on the scenic Gulf of Mexico Drive in the beautiful Longboat Key, Florida. Nestled in the heart of the stunning Sarasota Bay area, our location offers breathtaking views of the shimmering waters and vibrant sunsets that define Florida's Gulf Coast. Longboat Pass Bridge is not just a crossing point but a gateway to a world of natural beauty and outdoor adventure. Whether you're a local resident or a visitor, you'll find plenty to explore and enjoy in the surrounding area. From pristine beaches and lush parks to an array of water activities like fishing, boating, and kayaking, there’s something for everyone.

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.

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.

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.

The Longboat Bay Club is a premier institution located at 3200 Gulf of Mexico Drive on Longboat Key, Florida. This luxurious establishment offers a unique blend of lodging, real estate, and travel services. Whether you are looking for a relaxing getaway, a new home by the beach, or assistance in planning your next vacation, the Longboat Bay Club has everything you need. With stunning views, top-notch amenities, and exceptional customer service, this institution is the perfect destination for those seeking a truly unforgettable experience on the beautiful Gulf Coast of Florida.

Gulf Tides of Longboat Key is a charming lodging institution located at 3008 Gulf of Mexico Drive in the beautiful coastal town of Longboat Key, Florida. Nestled along the pristine shores of the Gulf of Mexico, this resort offers guests a tranquil and relaxing getaway with stunning ocean views and easy access to the beach. The accommodations are spacious and well-appointed, providing a comfortable and inviting atmosphere for guests to unwind and enjoy their stay. Whether you're looking for a romantic retreat, a family vacation, or a solo escape, Gulf Tides of Longboat Key offers the perfect setting for a memorable and rejuvenating experience.

The Resort at Longboat Key Club is a luxurious lodging institution located at 220 Sands Point Road in beautiful Longboat Key, Florida. This upscale resort offers stunning views of the Gulf of Mexico, pristine beaches, and world-class amenities. Guests can enjoy spacious accommodations, a championship golf course, tennis courts, a full-service spa, multiple dining options, and a marina for water activities. Whether you're looking for a relaxing getaway or an active vacation, The Resort at Longboat Key Club has something for everyone. Experience the ultimate in luxury and relaxation at this premier resort destination in the United States.

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.

Gulf Coast Property Management is a leading real estate agency located at 243 North Lime Avenue in Sarasota, Florida. Specializing in property management services, we understand the appeal of living in the Sarasota area, with its warm climate, inviting waters, and endless recreational opportunities. Whether you own rental properties near Siesta Key, Longboat Key, or in the Lakewood Ranch community, we are here to help you maximize the potential of your investments. Our experienced team is dedicated to providing top-notch services to property owners, ensuring that your rental properties are well-maintained and leased to qualified tenants. We are responsive, accessible, and committed to making the success of your investments a priority. With Gulf Coast Property Management, there are no hidden fees or surprise costs—just reliable and transparent service.

Welcome to Michael Saunders & Company - Longboat Key Real Estate, your premier destination for real estate and travel services in the heart of Florida's stunning Gulf Coast. Conveniently located at 440 Gulf of Mexico Drive, Longboat Key, Florida, our agency is dedicated to helping you discover the perfect property and travel experiences in this beautiful and serene locale. With a rich history of excellence, Michael Saunders & Company offers unparalleled expertise in the Longboat Key real estate market. Whether you're looking to buy, sell, or rent a property, our team of experienced and knowledgeable agents is here to guide you every step of the way. We pride ourselves on our personalized service, ensuring that your unique needs and preferences are met with the utmost care and professionalism.

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.

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!

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.

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.

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.

Happy Paddler Kayak Tours & EcoVentures is a family-owned travel agency located at 6844 Gulf of Mexico Drive in Longboat Key, Florida. Our team of water-loving naturalists and paddling instructors are dedicated to exploring and educating others about 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. Join us for a Coastal Island Tour where you can kayak with manatees, dolphins, and a variety of ocean life. Explore the mangrove tunnels at Lido Key, a popular destination for families. Experience the stunning Florida Gulf Coast sunsets on our Sunset Kayak Tour. Or rent a kayak or paddleboard for a half-day and chart your own course through the crystal clear waters of Longboat Pass.

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.

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.

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.

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.

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.

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.

Veranda Beach Club is a luxurious lodging destination located on the stunning Gulf of Mexico Drive in Longboat Key, Florida. This exclusive resort offers a range of beautiful accommodations, from cozy beachfront villas to spacious suites with breathtaking ocean views. Guests can relax by the pool, stroll along the white sandy beach, or enjoy a variety of water sports and activities. With its prime location and top-notch amenities, Veranda Beach Club is the perfect getaway for those seeking a tranquil and upscale vacation experience. Additionally, as a real estate agency, the institution also offers opportunities to own a piece of paradise in this desirable coastal community.

Dog Island is a charming and pet-friendly institution located on the Gulf of Mexico Drive in Longboat Key, Florida. This unique destination offers a variety of accommodations including a campground, lodging options, and a beautiful park for both humans and their furry friends to enjoy. With stunning views of the Gulf of Mexico and plenty of outdoor activities to partake in, Dog Island is the perfect spot for a relaxing getaway with your beloved canine companion. Whether you choose to pitch a tent, stay in a cozy cabin, or simply explore the park grounds, Dog Island provides a peaceful and picturesque setting for a memorable vacation experience.

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.

SeaHorse Beach Resort is a charming lodging establishment located at 3453 Gulf of Mexico Drive on the beautiful Longboat Key in Florida, United States. Situated right on the Gulf of Mexico, this resort offers guests a peaceful and relaxing retreat with stunning ocean views. With comfortable accommodations, friendly staff, and a variety of amenities, SeaHorse Beach Resort is the perfect destination for a beach vacation. Whether you're looking to relax on the sandy shores, take a dip in the crystal-clear waters, or explore the nearby attractions, this resort has something for everyone. Welcome to SeaHorse Beach Resort, where your beach getaway awaits.

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.

Welcome to Public Beach Access on Longboat Key, Florida! Nestled at 6399 Gulfside Road, our beautiful beach access points offer you a serene escape to the pristine shores of the Gulf of Mexico. Longboat Key is known for its tranquil beaches, bordered by private homes and condominiums, but our public access points ensure everyone can enjoy the natural beauty of this coastal paradise. Explore the 12 public beach access points along Gulf of Mexico Drive, each marked by distinct blue and white signs. While these access points do not offer facilities like bathrooms or lifeguards, restrooms are conveniently located at the Bayfront Park parking area. Please note that alcohol is prohibited on the beach, in keeping with Longboat Key's regulations.

Cabana Beach Club is a luxurious lodging institution located on the pristine shores of Longboat Key, Florida. Situated at 5851 Gulf of Mexico Drive, this exclusive beach club offers guests a tranquil and upscale retreat with breathtaking views of the Gulf of Mexico. The Cabana Beach Club features well-appointed accommodations, including spacious rooms and suites, as well as a range of amenities such as a private beach, swimming pool, and on-site dining options. Whether you're looking for a romantic getaway or a relaxing family vacation, Cabana Beach Club provides the perfect setting for a memorable stay in paradise.