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.
135 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Notice: This property has recently undergone thoughtful updates, including a stunning new six-seat dining table, two stylish and cozy new chairs in the living room, and more! Brand new photos have been uploaded as of March 2026.
This stunning villa has been
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This Palmetto Dunes beach home features 4 bedrooms and is only a short walk to the beach—that is, if you ever want to leave this gem!
15 Sea Lane features a spacious open floor plan and plenty of natural sunlight! Unwind in the living room as you watch TV on
15 Sea Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning 5-bedroom, 5.5-bathroom oceanfront home is nestled in the heart of North Forest Beach, offering an unforgettable coastal experience with sweeping views of the Atlantic. As you step through the bright and welcoming entryway, you are immediately
3 Dune Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Modern comforts meet the classic styling of this traditional beach home. If you are looking for a house that has the look and feel of the beach house from your childhood memories, look no further. The home has gone through a complete renovation to restore it
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trai
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning, brand-new property was just completed in June 2025 and is ready to welcome its very first guests!
The heart of the home lies upstairs, where the main living room impresses with vaulted ceilings and a wall of windows that flood the space with n
10 Cassina Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or friends\' getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along! As soon as the sun comes up, your days
43 South Beach Lagoon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the tranquil charm of a beach vacation at 25 Singleton Beach, a grand and luxurious 7-bedroom retreat designed for unforgettable seaside getaways. This stunning brand-new home boasts large glass doors and windows that flood the interior with natura
25 Singleton Beach
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
As soon as you step through the front door of 4202 Windsor Court North, expansive views of the Atlantic Ocean greet you, framed by natural dunes and swaying palms. The living area is warm and inviting, furnished with Tommy Bahama Bali Hai rattan bamboo pieces
4202 Windsor Court North
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
1506 Villamare, Luxury 5th Floor, Closest to the Beach, Views All Around
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!
Nestled i
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
From the moment you arrive, the home welcomes you with its inviting façade featuring two balconies, a cozy front porch, and a secluded swing-bench nook tucked to the side, perfect for morning coffee or a quiet evening moment.
Stepping inside, you\'re greeted
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
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