Longboat Key Vacation Homes for Sale

Bay Isles Harbor, Longboat Key - Stunning 4BR/5.5BA, 5,080 SF waterfront home in the Bay Isles Harbor section of Longboat Key. Unique Multiple Circular Pad Architectured home blends luxury, contemporary style and Costal living. This home features 16 foot great room with soaring tongue-and-groove ceilings and floor-to-ceiling windows showcasing sweeping water views.

Experience unparalleled luxury in this beautifully updated 3-bedroom condo at the highly coveted L’Ambiance condominium behind the exclusive gates of the Longboat Key Club. This seventh floor sabal floorplan offers sweeping views of the Gulf of Mexico, the Bay and downtown Sarasota.

Experience elevated coastal living in this updated, elegantly styled waterfront residence in the coveted community of Country Club Shores on South Longboat Key.

PreConstruction. Soon to grace Longboat Key, an exquisite coastal contemporary masterpiece by Brista Homes awaits, boasting a generous 4,176 square feet of luxurious living space on a spacious .42-acre residential parcel. This meticulously designed sanctuary encompasses five bedrooms, each featuring its own ensuite bath, providing ultimate comfort and privacy.

Gulf-Front Luxury Living at Vizcaya on Longboat Key! Experience refined coastal living in this exceptional three-bedroom residence at Vizcaya at Longboat Key, a boutique beachfront community offering the comfort of a single-family home paired with first-rate amenities.

Discover an elegant and gracious two-bedroom residence featuring spacious rooms, expansive glass windows, and soaring ceilings that create an airy, inviting atmosphere. The well-appointed gourmet kitchen boasts top-of-the-line Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, and a side-by-side refrigerator, perfect for culinary enthusiasts.

BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only.

The Quintessence of Coastal Living: A British West Indies Masterpiece on Longboat Key - Where Architecture Meets Paradise. Offered turn-key, this exquisite 4,000+ sq. ft., 4-bedroom, 4.5-bath residence in Longboat Key’s prestigious Bonaire subdivision is a rare union of refined British West Indies architecture and the serene beauty of Florida’s Gulf Coast.

DIRECT BEACH FRONT WALKOUT !! Completely redone in 2024!!The west facing private terrace off the living room and master bedroom has the exclusive feature of a Gulf front terrace with a private staircase that leads directly to the sandy beach and azure waters of the Gulf of Mexico. This rarely available floor plan is a stunning residence with front and back terraces.

Significant price improvement on this beautifully maintained canal home in Country Club Shores, one of Longboat Key’s premier waterfront communities. This solid-block residence offers 4,438 sq. ft. of bright, open living with wide sailboat-water canal views and a layout ideal for full-time or seasonal living.

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Why choose between breathtaking beach views, serene golf course vistas or the twinkling city lights when you can have them all? Welcome to Regent Place on Longboat Key, where this sixth-floor residence offers 270-degree panoramic views spanning the Gulf of Mexico, Sarasota Bay and downtown Sarasota.

GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary masterpiece by Floridian Crafted Homes, perfectly positioned on Longboat Key with breathtaking Gulf and Bay views. This 13 FEET ELEVATED, hurricane-fortified residence offers 5 bedrooms, 5 full bathrooms, and 2 partial bathrooms across 4,176 square feet of luxurious living space.