TOP 30 Vacation rental properties 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.

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.

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!

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.

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.

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.

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 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 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.

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.

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.

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.

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.

Zilli Villa is a luxurious and elegant institution located at 4235 Gulf of Mexico Drive in Longboat Key, Florida, United States. This stunning property offers a serene and picturesque setting for guests to relax and unwind. With spacious accommodations, modern amenities, and attentive service, Zilli Villa is the perfect destination for a getaway or special event. Whether you are seeking a peaceful retreat or a memorable celebration, Zilli Villa is sure to exceed your expectations.

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.

Sand Cay Beach Resort is a luxurious beachfront property located at 4725 Gulf of Mexico Drive in Longboat Key, Florida. This stunning resort offers a range of real estate options, from beautiful beachfront condos to cozy cottages. Whether you're looking for a vacation rental or a permanent home, Sand Cay Beach Resort has something for everyone. With its prime location on the Gulf of Mexico, guests can enjoy breathtaking views, white sandy beaches, and a host of amenities such as a pool, tennis courts, and direct beach access. The resort also offers concierge services to help guests make the most of their stay in this idyllic seaside paradise. Experience the ultimate in beachfront living at Sand Cay Beach Resort.

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 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.