Longboat Key Vacation Homes for Sale

Arrive by private elevator into this 2BR + den, 3.5BA residence offering 2,550 sq. ft. in Grand Bay. Wood floors run throughout the main living areas, leading to floor-to-ceiling sliders with views of the Harbourside Golf Course and Sarasota Bay. The covered terrace extends the living space and is well suited for enjoying daylight and coastal breezes.

Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water.

Located in the gated waterfront community of Coreys Landing within Bay Isles, this beautifully maintained 3BR residence offers refined design, comfort, and privacy. A paver walkway and lush tropical landscaping lead to the home’s centerpiece - a private courtyard pool surrounded by high privacy walls and tropical foliage, creating a tranquil space for relaxing or entertaining.

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy the best of island living in this beautifully remodeled and property remediated single-level home on Longboat Key. Perfectly positioned in a desirable mid-Key location on a quiet, friendly street, this coastal retreat combines relaxed sophistication with modern comfort.

Experience the best of Florida’s Gulf Coast in this remodeled and elevated single-family home, ideally located on a quiet street that ends at Sarasota Bay and includes deeded beach access. Surrounded by the tropical beauty of Joan M. Durante Park’s nature preserve, this residence blends modern coastal design with the serenity of island living.

Timeless sophistication meets resort-style elegance in this fully renovated 3-bedroom residence at the coveted Players Club on Longboat Key. Ideally situated on the sought-after south end of the island, this home places you moments from the prestigious St. Regis Hotel, the Longboat Key Club, Publix, and the upscale dining, boutique shopping, and cultural attractions of St.

Welcome to Your Waterfront Paradise! Discover this coastal retreat in the highly desirable Sleepy Lagoon community, perfectly positioned on a deep-water, saltwater canal just seconds from the Intracoastal and the Gulf.

Embrace beachfront living with this two-bedroom, two-bath residence, offering mesmerizing direct views of the Gulf of Mexico. An exceptional feature is the oversized private terrace with breathtaking ocean views, a rarity in beachfront properties. Your private rooftop terrace seamlessly connects to your balcony, extending your outdoor oasis to over 60 feet.

FULLY RENOVATED - Set high on the 10th floor with direct Gulf and beachfront vistas, this 2BR, 2BA residence in the Islander Club offers a front-row seat to a breathtaking panorama on Longboat Key. From the moment you step through the foyer, the horizon opens wide, unveiling sweeping blues and azures that stretch up the shoreline and out to the Gulf.

Sands Point, a sought-after beachfront community within the gates of the Longboat Key Club, set on the gorgeous southern tip of Longboat Key. This newly remodeled 3BR/2BA, split plane with a large open living space to relax or entertain family and friends.

Nestled behind the exclusive gates of the Longboat Key Club, Longboat Key Towers stands as one of the island’s most distinguished Gulf-front communities.

Under contract-accepting backup offers. Spectacular Gulf Front Views! West Exposure With Amazing Sunset Views! This Private Boutique Building Located Directly On The Beach in Longboat Key! With Only 9 Total Units In The Building, This Condo Offers Excellent Privacy, Direct Beach Access and Resort Style Amenities at Pelican Harbour. Featuring 3 Bedrooms & 3 Washrooms, With 1660 Sq.Ft.