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.


Properties Available 43 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This gorgeous Sea Pines villa has been recently renovated and features golf and lagoon views. Walk into an open-concept kitchen, dining room, and living room. Relax on either of the comfortable couches in the living room and watch your favorite programs on th
Pet-Friendly Pet-Friendly
Pet-Friendly
Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
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3 Lighthouse Road Villa Fairway Collection Icon
Villa - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (98)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 435 Captain\'s Walk overlooks the pool out to the ocean! Lots of recent updates! 435 Captain\'s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that overlooks the pool and out to the ocean. A beautiful, updated villa with great views—you couldn\'t ask
Oceanfront Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
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435 Captains Walk
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (50)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably. The first floor features a very open floor plan that offers easy access between the multiple living
Hot HOT 73
2 Royal Tern Icone Collection Icon
House -
Bedrooms 5 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 14 guests
Rating 5 (25)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This oceanfront home offers unforgettable views and a private pool, spa, a game room and an open great room. The open floor plan is a must and is perfect for entertaining. The gourmet kitchen features updated appliances and is perfect for gathering together.
Hot HOT 76
7 Guscio Way Icone Collection Icon
House -
Bedrooms 8 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 25 guests
Rating 4.9 (41)
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!
Oceanfront Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
533 Shorewood Place Icone Collection Icon
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (33)
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
Hot HOT 50
23 Black Skimmer Icone Collection Icon
House -
Bedrooms 8 bedrooms
Bathrooms 9 baths
Half Bathrooms 1 half bath
Guests 26 guests
Rating 5 (21)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautifully renovated 3-bedroom, 2.5-bath home has an open floor plan. The living room has ample room to relax and watch TV on the large flat screen; the dining area seats six people; and the kitchen has stainless steel appliances, granite counters, and
26 Forest Drive
House -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (53)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 9 Armada is a gorgeous second row home directly on the beach path in Palmetto Dunes Resort. This spacious 6,800 square foot home is perfect for entertaining, dining, reading, or relaxing! The kitchen features granite counters, two sinks, two dishwashers, a w
9 Armada Icone Collection Icon
House -
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 1 half bath
Guests 19 guests
Rating 5 (13)
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
Oceanfront Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
27 South Beach Lagoon
House -
Bedrooms 9 bedrooms
Bathrooms 10 baths
Half Bathrooms 1 half bath
Guests 28 guests
Rating 5 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 2-bedroom villa has been recently renovated and is the perfect oasis for a beach vacation. Nestled in the private oceanfront complex of Palmetto Dunes with perfect access to the beach and pool, the property features a complex pool, indoors and out! You w
Oceanfront Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
1204 Villamare Icone Collection Icon
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (45)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 3 Bedroom Villa in Harbour Town Area, Newly Renovated, and Golf View. Gorgeous renovations in 2020 make this villa the right choice for you. As you enter, you are greeted with a two-story, open, and airy space. This open-concept living, dining, and kitchen ar
Booked for Heritage Booked for Heritage
Booked for Heritage
2371 Racquet Club Fairway Collection Icon
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (42)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. With a scenic spot on the 11th hole, a private pool and spa to spend the day in, and spectacular views of the lagoon and golf course, this South Carolina home is the perfect vacation spot. Vaulted ceilings make this property feel comfortably spacious, which
Booked for Heritage Booked for Heritage
Booked for Heritage
38 Stoney Creek Road | Carolina Getaway Fairway Collection Icon
House -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (30)

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