Make Hilton Head Home for the Holidays
Planning Thanksgiving, Christmas or New Year’s on Hilton Head?
Bring everyone together at the beach this holiday season and secure the home you want now with a lower upfront deposit.
Reserve your holiday stay with just $550 down on homes or $350 down on villas.
From spacious homes made for gathering to cozy villas for a holiday escape, find your place to celebrate on Hilton Head Island.
Valid for new bookings. Low deposit offer applies to qualifying stays through March 31, 2027. Cannot be combined with other offers.
136 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
5 Jessamine Place is only a 10-minute walk to the best beach on Hilton Head Island!
This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quie
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautiful 3-bedroom villa with 3 full baths So close to the truly spectacular beaches of Palmetto Dunes Remodeled kitchen and baths Oversized covered deck overlooking the community pool.
Overlooking the Fazio Golf Course in Palmetto Dunes, this spacious town
57 Fazio Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property has recently undergone thoughtful updates, including a full kitchen renovation with new appliances, a fresh paint job, brand new bedding, brand new flooring, updated primary bathroom and more! Brand new photos have been uploaded as of March 2026
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy endless coastline views from this corner villa on the fifth-floor face of the Windsor Court South building in Palmetto Dunes. Take in breathtaking panoramic views from the screened porch or one of the many balconies that can be found off the living room
3507 Windsor Court South
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Walk into this welcoming coastal retreat and immediately feel right at home. Thoughtfully designed with spacious gathering areas and comfortable accommodations, this property offers the perfect setting for a relaxing Hilton Head getaway.
As you enter the hom
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful, nine-bedroom Beachcomber house sports a private pool and spa and provides expansive living spaces, as well as fabulous views of the beach and the Atlantic Ocean from the sweeping picture windows.
Situated on the most prestigious street in Sea
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
For a limited time, this property is offering complimentary pool heat for all new stays booked in October and November, making it even easier to enjoy the pool throughout your fall getaway.
32 Bradley Beach Road is a gorgeous beach house located a short walk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This Sea Pines home is nestled on a quiet street and places you only minutes away from Harbour Town and the sandy beaches!
Upon entry, you walk into the sitting room, which has plenty of comfortable seating around the cozy brick fireplace (not for guest use)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
504 Barrington Arms is a lovely three-bedroom, three-bathroom direct oceanfront condo on the fifth floor. Enjoy panoramic ocean views and updated furnishings and décor throughout. The dining area is adjacent to both the living room and the well-equipped kitch
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled within the picturesque surroundings of Palmetto Dunes on Hilton Head Island, South Carolina, this exquisite 5-bedroom house offers the epitome of coastal luxury living. Just a leisurely stroll away from the pristine sandy shores of the beach, this hom
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!
Indulge in the tranquility of coastal living with this exquisite 3-bedroom, 3-bathr
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Welcome to this stunningly renovated fourth row beach home in the heart of Palmetto Dunes, where luxurious indoor living, resort-style outdoor spaces, and breathtaking lagoon views come together on an oversized double lot just moments from the beach. Guests w
135 Mooring Buoy
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