TOP 30 Best Cottage 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 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 Walter Group Real Estate - Longboat Key Realtors, where over 22 years of expertise and a personalized approach have established us as Longboat Key's premier local real estate agency. Located at 440 Gulf of Mexico Drive, Longboat Key, Florida, we are your trusted partners in navigating the vibrant local real estate market. Janet and Steve Walter bring a wealth of local knowledge and a deep understanding of Longboat Key and its surrounding areas. Their commitment to providing personalized service and expert guidance ensures a smooth, stress-free experience whether you're buying or selling a property.

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.

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.

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.

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.

The Beach on Longboat Key Resort offers a serene and luxurious getaway on the stunning Gulf of Mexico. Located in Longboat Key, Florida, this lodging institution provides a peaceful escape with breathtaking views of the vibrant sunsets and turquoise waters. With all the amenities of a large resort, guests can enjoy a relaxing vacation without the crowds and noise. Experience a vacation of a lifetime at The Beach on Longboat Key Resort.

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.

Casa Del Mar Beach Resort on Longboat Key is a luxurious lodging option located at 4621 Gulf of Mexico Drive in Longboat Key, Florida. This beachfront resort offers stunning views of the Gulf of Mexico and a tranquil atmosphere for guests to relax and unwind. With spacious rooms, upscale amenities, and a range of on-site activities, Casa Del Mar Beach Resort is the perfect destination for a beach vacation. Whether you're looking to lounge by the pool, take a stroll along the sandy shores, or explore the nearby attractions, this resort has something for everyone. Experience the ultimate in comfort and hospitality at Casa Del Mar Beach Resort on Longboat Key.

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.

Longboat Terrace Corporation is a reputable real estate agency located at 5393 Gulf of Mexico Drive in Longboat Key, Florida, United States. Specializing in luxury properties and waterfront homes, the agency offers exceptional service and expertise in the local real estate market. With a team of experienced agents, Longboat Terrace Corporation is dedicated to helping clients find their dream home or investment property in this beautiful coastal community. Whether buying or selling, clients can trust Longboat Terrace Corporation to provide personalized assistance and guidance every step of the way.

Welcome to Ian Greenberg - Longboat Key & Sarasota Realtor, your trusted partner in real estate located at 388 Firehouse Lane, Longboat Key, Florida. Specializing in the vibrant communities of Longboat Key and Sarasota, Ian Greenberg brings a wealth of local knowledge and a commitment to exceptional service. Whether you're buying, selling, or investing, Ian is dedicated to guiding you through every step of the real estate process with professionalism and personalized attention. Discover the perfect property that suits your lifestyle and let Ian's expertise help you turn your real estate dreams into reality. Contact us today to experience the difference of working with a local expert who truly understands the market and is passionate about helping clients achieve their goals.

Welcome to Longboat Key Realtor, Judy Mitchell – your trusted partner in navigating the real estate landscape of beautiful Longboat Key, Florida. Conveniently located at 517 Bay Isles Parkway, Longboat Key, FL 34228, Judy Mitchell offers unparalleled expertise and personalized service to help you find your dream home or investment property in this stunning coastal paradise. With years of experience and a deep understanding of the local market, Judy is dedicated to providing exceptional service tailored to your unique needs. Whether you're buying, selling, or investing, she takes pride in guiding clients through every step of the real estate process with professionalism and integrity.

Welcome to Jordan Chancey - Real Estate in Bradenton, Sarasota, and The Islands, your trusted partner for luxury real estate services in Florida's beautiful Gulf Coast region. Conveniently located at 3007 Manatee Avenue West, Bradenton, Florida, our office is dedicated to providing proven expert guidance in the dynamic real estate markets of Bradenton, Sarasota, and the surrounding coastal areas. As a Luxury Home Marketing Specialist and Million Dollar GUILD Member, Jordan Chancey brings unparalleled expertise and a deep-rooted passion for the Gulf Coast. A sixth-generation resident of the area, Jordan combines local knowledge with a consistent track record as a Top Producer and Top 100 Team Leader in Florida. Whether you're seeking a serene escape on the world-famous Anna Maria Island or the quiet elegance and privacy of Longboat Key, Jordan's in-depth understanding of these communities ensures a seamless real estate experience.

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.

Welcome to Coldwell Banker Realty - Siesta Key, your premier real estate agency located in the heart of the vibrant and picturesque village of Siesta Key, Sarasota, Florida. Nestled at 5145 Ocean Boulevard, our office enjoys a prime location that captures the essence of this tropical paradise, renowned for its stunning beaches, exceptional dining, lively music, and eclectic shopping experiences. Our Siesta Key office is a hub of activity, attracting a diverse clientele from local residents to international visitors, all drawn by the allure of our prominently displayed property listings. With over 70 dedicated and experienced independent sales associates, we are committed to providing unparalleled customer service, ensuring you find the perfect property to match your lifestyle.

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.

Welcome to The St. Regis Longboat Key Resort, a luxurious beachside sanctuary opening in the summer of 2024. Nestled on Longboat Key, Florida's most coveted barrier island, our pristine 18-acre resort offers a blend of refined elegance and unparalleled personalized services. Experience the epitome of luxury where the Gulf of Mexico meets the sky and the white sands of one of the country's best beaches. Immerse yourself in the Florida lifestyle at our private beach, enjoy pools with personal cabanas, and explore our exclusive saltwater lagoon wildlife experience featuring resident Aldabra tortoises. Indulge in serenity at our world-class oceanfront spa with vitality pools, or savor the vibrant flavors at our chef-driven dining outlets.

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.

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.

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.

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.

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.