Windward Village Vacation Rentals

Discover the charm and convenience of Windward Village vacation rentals in the heart of Shipyard on Hilton Head Island. This peaceful villa community offers a relaxing coastal setting surrounded by towering pines, lush landscaping, and scenic lagoons, making it an excellent choice for families, couples, golfers, and snowbirds looking for a quiet island getaway.

Located within the gated Shipyard community, Windward Village provides easy access to Hilton Head's beautiful beaches, championship golf courses, world-class tennis and pickleball facilities, and miles of leisure trails. Guests can bike to the beach, spend the day exploring Shipyard's natural beauty, or take a short drive to the shopping, restaurants, and entertainment of Coligny Plaza and Shelter Cove Harbour & Marina.

Windward Village vacation rentals feature spacious villa layouts with comfortable living areas, fully equipped kitchens, private balconies or patios, and many overlook tranquil lagoons or beautifully landscaped grounds. Community amenities often include a private swimming pool, outdoor grilling areas, and convenient parking, providing everything you need for a relaxing vacation.

Shipyard is one of Hilton Head Island's most popular vacation destinations thanks to its central location and resort-style atmosphere. Golf enthusiasts can enjoy 27 holes of championship golf at Shipyard Golf Club, while tennis and pickleball players have access to the renowned Van Der Meer Tennis Center nearby. The beach is just a short bike ride or walk away, allowing guests to enjoy miles of wide sandy shoreline, breathtaking sunrises, and unforgettable days by the Atlantic Ocean.

Whether you're planning a summer beach vacation, a golf weekend, a family getaway, or an extended winter escape, Windward Village offers the perfect combination of comfort, convenience, and value. Browse our available Windward Village vacation rentals and experience everything Shipyard and Hilton Head Island have to offer.