TOP 30 Best Upscale vacation rentals 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.

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.

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.

Hilton Head, South Carolina is a luxurious lodging institution located at 8 Wimbledon Court on Hilton Head Island. This stunning resort offers guests a relaxing and upscale experience in the beautiful surroundings of South Carolina. With top-notch amenities, breathtaking views, and impeccable service, Hilton Head is the perfect destination for a memorable getaway. Whether you're looking to relax on the beach, play a round of golf, or explore the charming town, Hilton Head has something for everyone. Experience the ultimate in comfort and hospitality at Hilton Head, South Carolina.

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.

Windsor Court South at Palmetto Dunes is a luxurious lodging facility located at 57 Ocean Lane in Hilton Head Island, South Carolina. Situated in the beautiful Palmetto Dunes resort community, this institution offers guests a relaxing and upscale retreat with stunning ocean views and access to a variety of amenities. Whether you are looking for a romantic getaway, a family vacation, or a golfing trip, Windsor Court South at Palmetto Dunes provides a comfortable and elegant accommodation option for your stay on the island. With its prime location and top-notch service, guests can enjoy a truly memorable experience during their visit to Hilton Head.

Marriott's Grande Ocean is a luxurious lodging institution located at 51 South Forest Beach Drive in Hilton Head Island, South Carolina, United States. Nestled along the beautiful coastline, this resort offers stunning ocean views and upscale amenities for guests to enjoy. With spacious accommodations, multiple pools, a fitness center, and on-site dining options, Marriott's Grande Ocean provides a relaxing and memorable stay for visitors looking to experience the charm of Hilton Head Island. Whether you're seeking a romantic getaway, a family vacation, or a fun-filled retreat with friends, this resort is the perfect destination for a truly unforgettable experience.

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.

Chez Georges Bistro & Bar is a charming establishment located at 37 New Orleans Road in Hilton Head Island, South Carolina. This cozy bistro and bar offers a relaxed and inviting atmosphere for guests to enjoy delicious food and drinks. Whether you're looking for a casual meal or a night out with friends, Chez Georges has something for everyone. With a menu featuring a variety of tasty dishes and a wide selection of drinks, this restaurant is the perfect spot to unwind and indulge in a memorable dining experience. Visit Chez Georges Bistro & Bar for a taste of Southern hospitality and culinary delights in the heart of Hilton Head Island.

Barrington Court is a luxurious lodging institution located on Hilton Head Island in South Carolina, United States. Nestled in a beautiful coastal setting, Barrington Court offers guests a tranquil and upscale retreat with stunning views of the ocean. The accommodations are elegant and spacious, providing a comfortable and relaxing atmosphere for visitors. Guests can enjoy a range of amenities including a pool, fitness center, and access to the beach. Whether you are looking for a romantic getaway, a family vacation, or a peaceful escape, Barrington Court is the perfect destination for a memorable stay on Hilton Head Island.

Windsor Place II at Palmetto Dunes is a luxurious oceanfront resort located at 63 Ocean Lane in Hilton Head Island, South Carolina. This stunning property offers upscale accommodations with breathtaking views of the Atlantic Ocean and easy access to the pristine beaches of Palmetto Dunes. Guests can enjoy world-class amenities such as a sparkling swimming pool, fitness center, and tennis courts, as well as proximity to championship golf courses and top-rated restaurants. Whether you're looking for a relaxing beach getaway or an active vacation full of outdoor adventures, Windsor Place II at Palmetto Dunes is the perfect destination for your next trip to Hilton Head Island.

Southwind by Spinnaker Resorts is a luxurious lodging option located at 200 Southwind Drive in beautiful Hilton Head Island, South Carolina. This institution offers top-notch accommodations for travelers looking for a relaxing and enjoyable stay. Whether you are looking to rent a vacation property, purchase real estate, or plan your next travel adventure, Southwind by Spinnaker Resorts is the perfect destination. With stunning views, upscale amenities, and a convenient location near the beach, this institution is the ideal choice for your next getaway.

Marriott's Heritage Club is a luxurious lodging institution located at 12 Lighthouse Lane in the beautiful Hilton Head Island, South Carolina, United States. This resort offers spacious and elegant accommodations for guests looking to relax and unwind in a stunning beachfront setting. With top-notch amenities, including a pool, fitness center, and on-site dining options, Marriott's Heritage Club provides a perfect retreat for travelers seeking a blend of comfort and sophistication. Enjoy the charm of Hilton Head Island while indulging in the world-class hospitality of Marriott at this exquisite destination.

Hampton Place at Palmetto Dunes is a luxurious lodging option located at 41 Ocean Lane in Hilton Head Island, South Carolina, United States. This beautiful property offers upscale accommodations and top-notch amenities for guests looking to relax and unwind in style. Whether you're looking for a vacation rental, a real estate investment, or assistance planning your next trip, Hampton Place at Palmetto Dunes is the perfect destination. Experience the ultimate in comfort and convenience at this premier travel and real estate agency.

Royal Dunes Resort is a luxurious lodging facility located at 8 Wimbledon Court in Hilton Head Island, South Carolina. This stunning resort offers guests a peaceful and relaxing getaway with its beautifully landscaped grounds and upscale amenities. The spacious accommodations feature modern decor, fully equipped kitchens, and private balconies with breathtaking views of the surrounding area. Guests can enjoy the resort's outdoor pool, hot tub, fitness center, and tennis courts, as well as easy access to the nearby beach. With its convenient location and top-notch services, Royal Dunes Resort is the perfect choice for a memorable vacation on Hilton Head Island.

Marriott's Monarch at Sea Pines is a luxurious lodging institution located at 91 North Sea Pines Drive in Hilton Head Island, South Carolina, United States. Nestled in the picturesque Sea Pines Resort, this upscale property offers spacious accommodations, top-notch amenities, and stunning views of the surrounding area. Guests can enjoy access to pristine beaches, championship golf courses, and a variety of dining options. Whether you're looking for a relaxing getaway or an action-packed vacation, Marriott's Monarch at Sea Pines is the perfect destination for travelers seeking a memorable experience on the beautiful island of Hilton Head.

Carolina Club by Spinnaker Resorts is a luxurious lodging destination located at 200 Southwind Drive on Hilton Head Island in South Carolina, United States. This elegant resort offers spacious and well-appointed accommodations, perfect for a relaxing getaway or a family vacation. Guests can enjoy amenities such as a swimming pool, fitness center, and on-site dining options. With its prime location near the beach and various attractions, Carolina Club by Spinnaker Resorts is the ideal choice for those looking to experience the beauty and charm of 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.

Huntington by ResortQuest Hotel is a luxurious lodging institution located at 47 Ocean Lane, Hilton Head Island, South Carolina, United States. This stunning hotel offers a tranquil escape with its serene oceanfront location and upscale amenities. Guests can enjoy spacious and elegantly appointed rooms, a sparkling outdoor pool, a fitness center, and easy access to the beach. Whether you are looking for a romantic getaway or a family vacation, Huntington by ResortQuest Hotel is the perfect destination for a memorable stay on Hilton Head Island.

201 Colonnade is a luxurious lodging institution located at 201 Colonnade Drive in the beautiful Hilton Head Island, South Carolina, United States. Nestled in a serene and picturesque setting, this institution offers upscale accommodations and top-notch amenities for guests looking for a relaxing and unforgettable getaway. With its elegant decor, spacious rooms, and attentive staff, 201 Colonnade provides a perfect blend of comfort and sophistication for a truly memorable stay on Hilton Head Island.

South Beach Villas is a luxurious beachfront resort located at 225 South Sea Pines Drive in Hilton Head Island, South Carolina. Offering stunning views of the Atlantic Ocean, this upscale property features spacious villas with modern amenities and stylish decor. Guests can enjoy direct access to the beach, as well as a variety of on-site amenities including a swimming pool, fitness center, and tennis courts. With its prime location near popular attractions, dining, and shopping options, South Beach Villas is the perfect destination for a relaxing beach getaway.

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.