TOP 30 Cozy vacation rentals in Longboat Key, Florida

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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.

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.

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.

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.