Longboat Key Vacation Homes for Sale

A breathtaking tribute to the grandeur of Renaissance Venice, Serenissima—meaning “The Most Serene”—stands as one of Florida’s most revered residences. With its coveted architectural detail and Gulf-front address, this palatial estate is unmatched in design splendor, craftmanship, and artistry.

Under Construction. A vision of architectural brilliance, this extraordinary estate, nestled on a nearly two-acre site on the Gulf of Mexico, is poised to redefine comfortable coastal living. Currently under construction with a cost basis of approximately $25 million, this landmark residence is destined to be one of the most iconic homes on Sarasota’s Gulf Coast.

Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle.

Welcome to 5861 Gulf of Mexico Drive, a contemporary home that exudes Zen-like calm in a tropical jungle garden located on over an acre beachfront estate on Longboat Key. This masterpiece of tropical modernism spans a stunning 1.1 acres with 100 feet of direct Gulf frontage, offering privacy, breathtaking views, and a sophisticated lifestyle experience.

Under Construction. Enjoy the ultimate Longboat Key lifestyle in your very own direct Gulf Front private access with stunning Gulf of Mexico views! The progress at this Seaward Homes Curated Collection at 6489 Gulfside is moving right along, with completion expected by August of 2025. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail.

Sought after slice of beachfront paradise on the exclusive island of Longboat Key. Rarely available 2 acre property with 200 feet of beach frontage on the Gulf of America. Currently it hosts a quaint inn featuring ten suites and one cottage, all had been renovated with timeless old Florida decor.

Under Construction. You're in for something special with this new beachfront construction set to be completed by December, 2025. Located on over a quarter acre on Longboat Key, this contemporary luxury home is directly on the beach with stunning Gulf views. Designed with a modern coastal aesthetic, it’s built for both style and comfort. Inside no detail is overlooked.

Expansive, gated, waterfront family estate featuring custom designed main home along with a separate three bedroom guest home. Enjoy private deeded beach access and deep water dockage. This Private two acre gated estate on the north end of Longboat Key is a rare gem. Entrance, Driveway and Main home are illuminated with Bevelo gas lanterns.

This stunning Bayfront estate delivers over 880 feet of pristine Bayfront waterfront on nearly an acre and a half of prime point property. True Longboat Key gold. Special features of this home include five bedrooms, five full bathrooms, hardwood floors, sky-high ceilings plus walls of glass.

Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living.

Discover the pinnacle of coastal luxury at 50 Lighthouse Point Drive, an extraordinary estate nestled in the exclusive gated community of Lighthouse Point. A 13-acre community with only 16 estate homes on Longboat Key.

Experience the ultimate in beachfront living with this extraordinary 1.6-acre estate on Longboat Key, offering a rare 156 feet of direct frontage along the Gulf of Mexico. Embrace breathtaking water views and spectacular sunsets from every room and multiple balconies.