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 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 60
109 Island Club
Villa -
$135.00 - $278.00 / 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. 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 -
$1,858.00 - $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 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,
89 The Moorings
Villa -
$162.00 - $405.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Beautifully updated 3-bedroom villa in Shelter Cove. Come in, take a seat, and relax in the living room. The living room, kitchen, and dining room have an open layout. The kitchen has granite countertops, new stainless steel appliances, and smooth ceilings.
7474 Anchorage Villas
Villa -
$138.00 - $318.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (8)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This home is spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight stre
35 Shell Ring
House -
$139.00 - $2,213.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (5)
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. 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)
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
New Pictures New Pictures
New Pictures
2390 Lighthouse Tennis
Villa - Pet Friendly
$142.00 - $503.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 4.7 (9)
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 - $307.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This villa has plenty of space to move around. Walk into the first floor, where you have the kitchen, dining room, and living room leading out to a small patio. The living room has a small desk space, perfect for any last-minute work that needs to get done. T
16 Ocean Club
Villa -
$153.00 - $379.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (13)
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 -
$451.00 - $1,092.00 / 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. 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 66
10 Ketch Icone Collection Icon
House -
$971.00 - $3,222.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (9)

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