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Our curated Collection of Hilton Head vacation rentals includes carefully selected homes and villas that are among the finest properties on the island. We offer luxury rentals in Hilton Head Island's most popular locations including Sea Pines, Palmetto Dunes, North Forest Beach, South Forest Beach, and Shelter Cove. Choose from an impressive selection of oceanfront rentals, private homes, and pet friendly rentals. We offer rentals with private pools as well as properties with access to heated pools in addition to many other sought-after amenities including keyless entry, wifi internet, updated furnishings, expansive porches, fireplaces, garage access, and more. Our vacation rentals are handpicked to help create a memorable experience during your Hilton Head vacation.

8 properties available

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This Sea Pines villa is outfitted with elegance in every detail, offering guests complete coastal luxury. An alluring yet spacious layout offers guests plenty of room to spread out, all while being together. Upon entry, to the left, you will find the fully

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1838 Beachside Tennis

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 2 bedroom, 2-bath Beachside Tennis villa has panoramic views of Calibogue Sound. Located in the South Beach area of Sea Pines on the first floor of a five-story building, just steps to the pool and beach, When entering the villa, you will find the mast

Water View

Enjoy stunning water views from every room. Explore our water view properties.
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1866 Beachside Tennis Villa

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This waterfront villa in Sea Pines offers a blend of coastal charm and relaxed sophistication, with sweeping views of the Calibogue Sound from nearly every angle. Designed to host family and friends, the stunning villa features three bedrooms, two and a half

New Property

New arrivals, just released. Explore our most recent properties.
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1922 South Beach Club

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. 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.
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253 Captains Quarters

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 510 Mainsail is a gorgeous two-bedroom, two-and-a-half-bath, top-floor villa with breathtaking panoramic views of Shelter Cove Harbour. Designer-decorated, this property is perfect for a Hilton Head vacation and comfortably accommodates up to four people. Th

Water View

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

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to t

Booked for Heritage

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Penthouse 3-bed villa overlooking the world-famous Harbour Town Yacht Basin, just steps away from Harbourtown A great room with dual sofas facing a large flat-screen TV A set of sliders gives entrance to a whimsically tiled patio with a postcard-perfect view

Booked for Heritage