TOP 10 Best Upscale vacation homes in Hilton Head Island, South Carolina

Luxury Homes of Hilton Head is a full-service real estate agency located at 62A New Orleans Road in Hilton Head Island, South Carolina. Specializing in resort and luxury properties, we offer comprehensive services for all your homeownership needs. Our team goes above and beyond to provide exceptional service and expertise to meet our clients' expectations. Whether you're a first-time buyer or a seasoned investor, we are here to guide you through the process of owning a home on Hilton Head Island. We pride ourselves on offering the most up-to-date information about real estate on Hilton Head Island and Bluffton, including details about Homeowner's Associations, Condo Management Regimes, and Property Regulations.

Hilton Grand Vacations Club Ocean Oak Resort Hilton Head is a luxurious lodging option located at 41 South Forest Beach Drive in Hilton Head Island, South Carolina, United States. Nestled along the picturesque coastline, this resort offers guests a relaxing and upscale vacation experience. With spacious accommodations, top-notch amenities, and stunning ocean views, guests can unwind and indulge in the beauty of Hilton Head Island. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Hilton Grand Vacations Club Ocean Oak Resort Hilton Head has everything you need for a memorable stay.

The Island Club is a luxurious lodging destination located on Island Club Road in Hilton Head Island, South Carolina. This exclusive institution offers a range of upscale accommodations, including spacious villas and condos, all surrounded by pristine beaches and lush tropical landscapes. Guests can enjoy access to a variety of amenities, such as swimming pools, tennis courts, fitness facilities, and private beach access. Whether you're looking for a relaxing getaway or an action-packed vacation, The Island Club provides the perfect retreat for travelers seeking a tranquil and upscale experience on Hilton Head Island.

Hilton Head Plantation is a luxurious residential community located on Jingle Shell Lane in Hilton Head Island, South Carolina, United States. This prestigious institution offers an array of amenities including golf courses, tennis courts, swimming pools, marinas, and walking trails. Residents and guests can enjoy breathtaking views of the surrounding natural beauty and access to a variety of recreational activities. With its prime location on Hilton Head Island, Hilton Head Plantation provides a serene and upscale lifestyle for those seeking a peaceful retreat.

The Sales Gallery at Marriott Vacation Club in Hilton Head is a luxurious destination located at 50 South Forest Beach Drive, offering an exquisite experience in the heart of Hilton Head Island, South Carolina. This upscale lodging institution is designed to provide guests with unparalleled comfort and convenience, featuring elegant accommodations, top-notch amenities, and exceptional service. Whether you're looking for a relaxing getaway or a fun-filled vacation, the Sales Gallery at Marriott Vacation Club is the perfect choice for your next escape.

Experience ultimate luxury and relaxation at our stunning Oceanfront Estate Vacation Rental located at 18 Grey Widgeon Road, Hilton Head Island, South Carolina. This exquisite property offers breathtaking views of the ocean, spacious living areas, top-of-the-line amenities, and a private beach access. Perfect for a family getaway or a romantic retreat, this estate is the epitome of upscale coastal living. Indulge in the beauty of the surroundings and create unforgettable memories at this exclusive vacation rental.

WaterWalk at Shelter Cove Towne Centre Apartments is a luxurious real estate agency located in the heart of Hilton Head Island, South Carolina. Situated at 47 Shelter Cove Lane, this institution offers stunning waterfront apartments with breathtaking views of the marina. Residents can enjoy resort-style amenities such as a swimming pool, fitness center, and private balconies overlooking the serene waters. With top-notch customer service and a prime location within the vibrant Shelter Cove Towne Centre, WaterWalk is the perfect place to call home for those seeking a blend of luxury and convenience.

Sea Pines Country Club, located at 30 Governors Road in Hilton Head Island, South Carolina, offers a luxurious lifestyle that feels like home. With world-class amenities, members can enjoy gourmet dining, exciting activities and events, and exceptional service in resort-quality surroundings. The club provides a sanctuary where lifelong friendships are formed, making it the private side of Sea Pines. Indulge in the very best of everything at Sea Pines Country Club.

Located at 11 Lighthouse Lane on Hilton Head Island in South Carolina, Links, an American Grill is a premier dining destination within The Sea Pines Resort. Offering a wide range of accommodations, including villas, homes, and luxury hotel rooms, our resort is the perfect place to relax and enjoy all that Hilton Head has to offer. As a top golf destination, loved by PGA TOUR pros and enthusiasts alike, The Sea Pines Resort boasts stunning landscapes, sandy beaches, and family-friendly activities. Our resort restaurants provide a true Lowcountry dining experience, with menus inspired by South Carolina's vibrant culinary scene.

Marriott's Harbour Club is a luxurious lodging institution located at 144 Lighthouse Road in Hilton Head Island, South Carolina, United States. Situated in a picturesque coastal setting, this resort offers upscale accommodations and top-notch amenities for guests looking for a relaxing getaway. With spacious rooms, stunning views, and impeccable service, Marriott's Harbour Club is the perfect destination for those seeking a memorable vacation experience. Whether you're looking to unwind by the pool, hit the nearby beaches, or explore the charming town of Hilton Head Island, this institution provides the perfect home base for your stay.

The Plaza at Shelter Cove Shopping Center is a premier shopping destination located at 50 Shelter Cove Lane in Hilton Head Island, South Carolina. This bustling shopping mall offers a wide variety of stores, restaurants, and entertainment options for visitors to enjoy. From upscale boutiques to popular chain retailers, there is something for everyone at The Plaza. With its convenient location and picturesque surroundings, The Plaza at Shelter Cove Shopping Center is the perfect place to spend a day of shopping and dining on Hilton Head Island.

Sound Villas is a luxurious accommodation located at 251 South Sea Pines Drive in Hilton Head Island, South Carolina. Nestled in the heart of a vibrant community, this institution offers upscale villas with stunning views of the surrounding landscape. Guests can enjoy spacious living areas, modern amenities, and access to a range of recreational activities. Whether you're looking for a relaxing getaway or an adventure-filled vacation, Sound Villas provides the perfect setting for a memorable stay on the beautiful island of Hilton Head.

Port Villas is a luxurious waterfront community located on Port Villa Drive in Hilton Head Island, South Carolina, United States. Nestled along the picturesque shoreline, Port Villas offers stunning views of the water and easy access to boating and water activities. The well-appointed villas feature modern amenities and spacious living areas, perfect for relaxing and entertaining. Residents can enjoy a variety of on-site amenities, including a swimming pool, fitness center, and private dock. With its prime location and upscale accommodations, Port Villas is the ideal destination for those seeking a tranquil and upscale coastal living experience.

Magnolia Beach Rentals HHI offers luxurious lodging in paradise on Hilton Head Island. Located at 19 Wimbledon Court in South Carolina, United States, this institution provides a comfortable and upscale experience for guests. Whether you are looking for a relaxing beach vacation or an adventurous getaway, Magnolia Beach Rentals HHI has everything you need for a memorable stay. Enjoy the beauty of Hilton Head Island while staying in style at this exquisite accommodation.

Plantation Club Villas, Regime 20 is a luxurious lodging option located at 22 Lighthouse Road on Hilton Head Island, South Carolina. This institution offers a range of upscale accommodations for visitors looking to experience the beauty of the island. Whether you are looking for a relaxing vacation rental or a permanent residence, Plantation Club Villas, Regime 20 can assist you with your real estate needs. Additionally, their travel agency services can help you plan the perfect getaway to this stunning destination. Experience the ultimate in comfort and hospitality at Plantation Club Villas, Regime 20.

Barrington Arms Villas is a luxurious real estate and travel agency located at 75 Ocean Lane in Hilton Head Island, South Carolina, United States. Our villas offer stunning ocean views and upscale amenities, making them the perfect destination for a relaxing vacation or a permanent residence. With a prime location near the beach and top-rated restaurants and shops, Barrington Arms Villas is the ideal choice for those seeking a sophisticated and convenient lifestyle in Hilton Head Island. Contact us today to learn more about our available properties and vacation rental options.

220 Turnberry Village at Palmetto Dunes Resort is a luxurious lodging option located in the heart of Hilton Head Island, South Carolina. This beautiful resort offers stunning views of the surrounding landscape and provides guests with top-notch amenities and services. Whether you are looking for a relaxing getaway or an action-packed adventure, 220 Turnberry Village has something for everyone. With its convenient location and upscale accommodations, this resort is the perfect destination for a memorable vacation experience.

Sea Side Villa Complex is a luxurious beachfront resort located at 23 South Forest Beach Drive in Hilton Head Island, South Carolina. With stunning views of the ocean and direct access to the pristine sandy beaches, this complex offers a perfect getaway for those looking to relax and unwind. The villas are beautifully appointed with modern amenities and spacious layouts, providing a comfortable and stylish retreat for guests. The resort also features a sparkling pool, fitness center, and on-site dining options, making it a convenient and enjoyable destination for travelers seeking a beachfront escape. Experience the ultimate in coastal living at Sea Side Villa Complex.

4RentOnFripp.com, LLC is a real estate and travel agency located at 64 Davis Love Drive on Fripp Island, South Carolina. Our upscale vacation home is designed for couples and families looking to enjoy a beautiful and well-maintained rental property on Fripp Island. The home includes an elevator, ADA bathroom with shower, and a party deck for relaxation and entertainment. Additionally, two Club Car 6-seater golf carts are included with all rentals for easy transportation around the island. The vacation home was custom-built to accommodate elderly or wheelchair-bound guests, with comfortable furnishings and a fully stocked gourmet kitchen. Fripp Island is a private 3,000-acre community located near historic Beaufort, Savannah, Charleston, Hilton Head, and Edisto Beach. It offers cool sea breezes, moonlit beaches, two highly-rated golf courses, a tennis complex, and a full-service marina with access to stunning marshes.