Heritage Uncorked

Sip, stroll, and ride stress-free this Heritage Week.

Island Time guests enjoy seamless transportation to and from the tournament all week long—no parking hassles, no timing stress.

🚐 Shuttle & private ride options available
All guests receive 10% off transportation.

Easy, reliable rides so you can focus on enjoying Heritage.

If you have any questions, please call our office at 843-785-3456.

134 properties available

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful scenery of the marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? An expansive, gorgeous beach is just

Pet-Friendly

Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
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Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably. The first floor features a very open floor plan that offers easy access between the multiple living

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This home is spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight stre

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Located on a quiet street, with Harbour Town Golf Course just steps away, 35 Battery has a light, bright feel and an open, single-level floor plan. Upon entering the front door, a foyer leads guests directly into the living/dining room, which has cathedral ce

Booked for Heritage

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 245 Captains Quarters is the ideal villa for a small family getaway, offering picturesque views of the Intracoastal Waterway from your own private balcony, allowing you to fully immerse yourself in the tranquil atmosphere of Hilton Head. The fully stocked k

Water View

Enjoy stunning water views from every room. Explore our water view properties.
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245 Captains Quarters

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2390 Lighthouse Tennis Villa invites you to experience the Sea Pines Community on Hilton Head Island. In addition to its premier location surrounded by beautiful scenery, this well-appointed villa is an exceptional getaway retreat. From Harbour Town Marina to

Pet-Friendly

Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
Learn More

2390 Lighthouse Tennis

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Discover the ultimate island retreat in this newly built pet-friendly three-story home, perfectly designed for a relaxing getaway. With its elegant interiors and thoughtfully curated outdoor spaces, this stunning property is an oasis of comfort and style. T

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 9 Armada is a gorgeous second row home directly on the beach path in Palmetto Dunes Resort. This spacious 6,800 square foot home is perfect for entertaining, dining, reading, or relaxing! The kitchen features granite counters, two sinks, two dishwashers, a w

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This magnificently remodeled North Shore Place villa features two bedrooms. Walking into an open-concept floor plan. The master bedroom has a beautiful king bed and private ensuite bath. The ensuite bathroom features a walk-in shower. The guest bedroom has

103 North Shore Place

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures. The villa is designed to offer a perfect blend of modern ameniti

Water View

Enjoy stunning water views from every room. Explore our water view properties.
Learn More

253 Captains Quarters

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2519 Windsor Place is a beautifully appointed three-bedroom, three-bathroom oceanfront villa offering elevated coastal living from its top-floor location. With sweeping views of the Atlantic and the calming rhythm of the waves just beyond, this villa creates