Christmas Getaway
Spend Christmas in Paradise! Escape the cold and celebrate the holidays on beautiful Hilton Head Island! Picture this; warm ocean breezes, twinkling lights, and festive events for the whole family. Look forward to peaceful beach strolls or a cozy gathering by the fire, Hilton Head has the perfect mix of holiday magic and coastal charm.
We are now offering a 4-night minimum for homes and a 3-night minimum for villas over the holidays.
42 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
7 Sea Front is a recently updated, elegant 2nd row ocean home with a golf simulator. Located in Burkes Beach, this home has 7 bedrooms with great porches, a private pool, and a game room featuring a brand new golf simulator and ping pong table. This home is
7 Sea Front
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.
This completely renovated Palmetto Dunes villa is sure to make you feel right at home! Welcome to 89 The Moorings, featuring 2 bedrooms and 3 bathrooms with enough room to host up to 8 guests very comfortably. Guests can enjoy the feel of brand new flooring,
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.
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.
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.
Please Note: Exterior improvement work will be taking place at Lighthouse Road Villas beginning the week of 4/20/2026. Work will include tree removal, driveway resurfacing, new sidewalk installation, electrical updates, and landscaping. Tree removal will begi
3 Lighthouse Road Villa
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 7,500-square-foot beachfront home features a private, in-ground pool with a spa and a patio overlooking the Atlantic Ocean. With private beach access, this home is perfect for those long beach days! The kitchen is equipped with stainless steel appliances
23 Black Skimmer
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
32 Bradley Beach Road is a gorgeous beach house located a short walk to the beach, sleeping 9 guests in 3 bedrooms, 3 bathrooms, and a bonus room. This lovely home is exceptionally well maintained and has ample room to spread out in the living room, which has
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This two-story Fazio villa boasts peaceful golf course views and is perfect for a family vacation. With close proximity to the spectacular beaches of Palmetto Dunes with new furnishings, flooring and remodeled baths, and an oversized covered deck overlooking
26 Fazio Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful oceanfront property features three spacious bedrooms, providing ample space for a relaxing and enjoyable stay. A gorgeous foyer with a spiral staircase ascends to a massive open floor plan with open living, dining, and kitchen areas with high-e
101 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Located in Palmetto Dunes and only a few minutes walk to the beach, this four bedroom home has all you need for the perfect stay on the island. 3 Cartgate offers four bedrooms and four and a half bathrooms, large spacious rooms, an open kitchen and private po
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