Lock in your stay with a low deposit
Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.
Lock in your stay with a low deposit of $550 on homes & $350 on villas!
Valid for any booking between 9/1/26 - 3/31/27.
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.
This offer cannot be combined with other offers. Valid for new stays only.
136 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautifully updated 3-bedroom villa in Shelter Cove. Come in, take a seat, and relax in the living room. The living room, kitchen, and dining room have an open layout. The kitchen has granite countertops, new stainless steel appliances, and smooth ceilings.
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property will be undergoing construction and unavailable for rental during 2026. If you have any questions, please reach out to us at or call
This beautifully upgraded vacation home combines sophisticated design, high-end finishes, and abundant natur
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
No details were missed in this amazing 3-bedroom Palmetto Dunes home. Amazing golf course views greet you as soon as you walk in the door. The large living room\'s main sitting area has a sleeper sofa, a loveseat, and a desk.
Heading further through this ho
10 Troon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property now offers an exciting new amenity with a free pickleball and tennis pass in Palmetto Dunes, which includes two free hours of court time every day of your stay!
Find tranquility in this cozy two-bedroom, two-and-a-half-bath Palmetto Dunes villa
8103 Wendover Dunes
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
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
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
The property is situated among the palmettos and oak trees of Hilton Head Island and steps away from the Atlantic Ocean. The lapping of the waves on the beach of this oceanfront home will put you to sleep, while the bedrooms on the street side of the house ge
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
533 Shorewood is an amazing 2-bedroom, 2-bathroom oceanfront villa with a pool and ocean views! This stunning beach condo sleeps 7 and is on the 5th floor with elevator access, featuring all new furniture and décor, a community pool, beach access, and more!
533 Shorewood Place
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Tucked away on a quiet cul-de-sac in the heart of Sea Pines, 28 Battery Road is a delightful single-level retreat designed for effortless coastal living.This charming home offers a thoughtful layout, inviting gathering spaces, and a serene outdoor oasis, maki
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home sits in the prestigious Palmetto Dunes Resort and offers panoramic ocean views from every angle.
The great room, kitchen, and dining area make up the great room of the home; the extremely open floor plan allows for an easy flow and plent
10 Ketch
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Thoughtfully refreshed and beautifully appointed, this 4-bedroom, 4.5-bath home in the heart of Sea Pines Plantation offers inviting coastal comfort with multiple gathering spaces, serene golf-course views, and a renovated pool deck perfect for relaxing days
2 Tupelo Drive
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been freshly updated with brand new exterior paint, kitchen countertops, renovated bedrooms and bathrooms, a new grill, and more exciting upgrades throughout! Photos have been updated to reflect these updates as of February 2026.
This pet-frien
36 Red Oak
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