The 30 Best Florida vacation rentals in Longboat Key, Florida

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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.

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.

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.

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.

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.

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.

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.

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.

Kokomo Charters is a luxury travel agency located at 5 Bayfront Drive in Sarasota, Florida. We specialize in providing private boat charters in the Sarasota area, including Siesta Key, Anna Maria Island, Lido Key, Casey Key, and Longboat Key. Our visitors consistently praise us as the highlight of their vacation, while locals book us regularly to impress their guests. Our fleet includes the beautiful 37-foot Sea Ray "Top Shelf" and the massive 50-foot three-story yacht "Memory Maker." Both vessels are yacht certified and offer a luxurious and upscale boating experience unlike any other in the market. Each charter is completely customized to your preferences, ensuring an unforgettable day for you and your crew.

ULTRA-MARINE is a premier store located at 520 Cedar Street in Longboat Key, Florida, offering a wide range of high-quality boats and yacht charters. Specializing in Zodiac Inflatable Boats, Duffy Electric Boats, Yacht Charters, Boat Charters, and Electric Motors, ULTRA-MARINE is your go-to destination for all your boating needs. At ULTRA-MARINE, we pride ourselves on providing top-of-the-line ZODIAC boats that are unmatched in quality, safety, and performance. Our experienced team will help you find the perfect ZODIAC model to suit your specific needs, whether you're looking for a versatile MEDLINE boat for family outings or a stylish YACHTLINE RIB tender for your yacht.

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.