The 30 Best Vacation rentals in Longboat Key, Florida

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.

Sea Grape Inn is a charming lodging establishment located on the picturesque Longboat Key in Florida. Situated at 5125 Gulf of Mexico Drive, this inn offers comfortable accommodations with a touch of coastal elegance. Whether you are looking for a relaxing beach getaway or a romantic retreat, Sea Grape Inn is the perfect choice for your stay. In addition to providing lodging services, Sea Grape Inn also offers real estate and travel agency services to help you make the most of your time in this beautiful destination. Book your stay at Sea Grape Inn and experience the beauty of Longboat Key, Florida.

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.

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.

Beaches of Longboat Key is a luxurious oceanfront institution located at 775 Longboat Club Road in Longboat Key, Florida. This exclusive beachfront property offers stunning views of the Gulf of Mexico and pristine white sandy beaches. Guests can relax in style in beautifully appointed accommodations, enjoy world-class amenities, and indulge in gourmet dining options. Whether you're looking for a romantic getaway, a family vacation, or a relaxing retreat, Beaches of Longboat Key provides the perfect setting for a memorable experience by the sea.

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!

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.

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.

INFINITY Longboat Key is a luxurious waterfront institution located at 4765 Gulf of Mexico Drive in Longboat Key, Florida, United States. This prestigious destination offers unparalleled views of the Gulf of Mexico and a serene beachfront setting. With world-class amenities and exceptional service, INFINITY Longboat Key is the ideal retreat for those seeking a sophisticated and relaxing escape. Whether you are looking to unwind by the pool, indulge in gourmet dining, or explore the natural beauty of the surrounding area, this exclusive institution promises a truly unforgettable experience.

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.

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.

Longboat Bay Charters is a premier travel agency located at 518 Bayview Drive in beautiful Longboat Key, Florida. Specializing in luxury yacht charters, Longboat Bay Charters offers unforgettable experiences on the crystal-clear waters of the Gulf of Mexico. Whether you're looking for a romantic sunset cruise, a day of fishing with friends, or a week-long island-hopping adventure, our experienced crew will ensure your trip is nothing short of spectacular. Contact us today to start planning your dream getaway with Longboat Bay Charters.

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 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 Gina Ursini - Brista Realty, your premier real estate agency located in the heart of Longboat Key, Florida. Situated at 388 Firehouse Lane, our agency is dedicated to providing exceptional real estate services tailored to your unique needs. With a deep understanding of the Longboat Key area, Gina Ursini and her team offer unparalleled expertise in buying, selling, and investing in local properties. At Gina Ursini - Brista Realty, we pride ourselves on delivering personalized service, ensuring that every client receives the attention and care they deserve. Whether you're looking for a luxurious waterfront home, a cozy vacation retreat, or an investment opportunity, our extensive knowledge of the local market will guide you every step of the way.

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.

Sara Bay Sailing School and Charter is a premier institution located at 4134 Gulf of Mexico Drive in Longboat Key, Florida. Our school offers top-notch sailing lessons and charters for all levels of experience, from beginners to advanced sailors. With a team of experienced instructors and a fleet of well-maintained boats, we provide a safe and enjoyable learning environment for all our students. Whether you are looking to learn the basics of sailing or want to improve your skills, Sara Bay Sailing School and Charter is the perfect place for you. Join us for an unforgettable sailing experience on the beautiful 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.

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.

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.

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.

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.

Whitney Beach is a charming lodging institution located at 8240 Florida 789, Longboat Key, Florida, United States. Nestled in a beautiful coastal setting, Whitney Beach offers guests a serene and relaxing atmosphere to unwind and enjoy their vacation. With comfortable accommodations and top-notch amenities, guests can enjoy a memorable stay at this idyllic retreat. Whether you're looking to relax on the beach, explore the nearby attractions, or simply soak in the stunning views, Whitney Beach is the perfect destination for a peaceful getaway.