Thanksgiving Getaway

Create a new tradition of spending the holidays by the ocean, making lasting memories with your loved ones. Avoid the stress of hosting and take a more relaxed route by spending Thanksgiving with us. With ample space, activities for everyone, and the stunning beach at your doorstep, it's the perfect way to enjoy the season. Want to unwind even more? Let our Luxury Concierge arrange in-house services for you: grocery delivery, catering meals and activities for your entire crew.

We are now offering a 4-night minimum for homes and a 3-night minimum for villas over the holidays.



Properties Available 20 properties available
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
Hot HOT 96
15 Sea Lane Fairway Collection Icon
House -
$265.00 - $843.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (16)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Direct Oceanfront 3 bedrooms Villa with gorgeous renovations This 3-bedroom, 3-bath villa offers a comfortable vacation for friends or family groups. Enjoy ocean views with access to your private balcony through the living room or master bedroom. The living
Oceanfront Oceanfront
Oceanfront
404 Barrington Arms
Villa -
$227.00 - $1,060.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (25)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 103 Seacrest is beautifully decorated and fully renovated for your comfort and convenience. Here, you will experience only the best. This charming property features two bedrooms, creating a cozy and inviting atmosphere for your stay. Allow me to paint a pictu
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103 Seacrest Icone Collection Icon
Villa -
$135.00 - $525.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)
Welcome to The Sandbox! Newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next Hilton Head Island family getaway. This home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. The living room is well-appointed and spacious, an
Hot HOT 111
9 Guscio Way Icone Collection Icon
House -
$959.00 - $3,506.00 / per night
Bedrooms 8 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 5 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This charming two-bedroom, two-story townhouse is located in the highrise building at the oceanfront Island Club, featuring a lagoon view from the private deck. Walk right out to the grounds from the deck or spend your evening cooking dinner with the family i
Hot HOT 81
109 Island Club
Villa -
$135.00 - $316.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (1)
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
4 Quail Street
House -
$385.00 - $1,241.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 11 guests
Rating 4.9 (10)
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
2371 Racquet Club Fairway Collection Icon
Villa -
$218.00 - $699.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
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
Hot HOT 67
10 Ketch Icone Collection Icon
House -
$987.00 - $3,222.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (9)
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
27 South Beach Lagoon
House -
$1,366.00 - $5,613.00 / per night
Bedrooms 9 bedrooms
Bathrooms 10 baths
Half Bathrooms 1 half bath
Guests 28 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This quaint 3 bedroom , 3 bathroom, two story private condo gives you the feel of the coastal charm. As you step into the first level of the condo, you will find the fully equipped kitchen including a Keurig coffee maker, has plenty of counter space and cabin
52 Ocean Breeze
Villa -
$92.00 - $351.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (4)
**THIS OCEANFRONT HOME IS A NON-SMOKING PROPERTY (INCLUDING OUTDOOR SPACES) AND DOES NOT ALLOW ANY PETS OR ANIMALS IN OR ON PROPERTY.** Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunning oceanfront oasis sits in the heart of Palmetto Dunes. As soon as you step through the front doors, the luxu
Oceanfront Oceanfront
Oceanfront
19 Armada Icone Collection Icon
House -
$1,861.00 - $5,722.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 15 guests
Rating 5 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The prim
212 Breakers
Villa -
$115.00 - $326.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Rating 5 (9)

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