TOP 30 Relaxing beach vacation homes for rent in Longboat Key, Florida

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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.

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.

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.

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.

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.