Celebrate Thanksgiving on Hilton Head
Arrive any day with a 4-night minimum for villas and a 5-night minimum for homes.
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146 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room. There are lots of books to read; there is lots of seating on
30 Ruddy Turnstone | Ruddy Retreat
House -
$436.00 - $1,828.00 / per night
5
bedrooms
6
baths
14
guests
4.9
(11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely remodeled Sea Pines home sits on the 11th fairway and 15th green of the Harbour Town Golf Course!
With 5 bedrooms and 6 bathrooms, this sunlight-filled home can host up to 14 guests comfortably. As you enter the home, you are met with an extr
100 Baynard Cove
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House -
$511.00 - $1,537.00 / per night
5
bedrooms
5
baths
1
half bath
14
guests
5
(7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Discover the ultimate lagoon-front escape at this beautifully renovated home, complete with a private fishing dock and just a 5- to 10-minute walk from the beach, the Dunes House, and the Tennis and Pickleball Center.
Step into the first level, where new vi
9 Saint George
House -
$349.00 - $924.00 / per night
4
bedrooms
4
baths
1
half bath
12
guests
5
(3)
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
2390 Lighthouse Tennis
Villa -
$142.00 - $503.00 / per night
1
bedroom
1
bath
4
guests
4.7
(9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy the amazing ocean views from this lovely 2-bedroom, 2-bathroom renovated Windsor II villa. The dining table offers seating for 6, and the adjacent breakfast bar offers bar stool seating for 3.
Enjoy the spacious living room with a brand new sleeper sof
2216 Windsor II
Villa -
$171.00 - $457.00 / per night
2
bedrooms
2
baths
6
guests
5
(7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to t
729 Schooner Court
Villa -
$169.00 - $896.00 / per night
2
bedrooms
2
baths
1
half bath
4
guests
4.8
(14)
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
404 Barrington Arms
Villa -
$336.00 - $781.00 / per night
3
bedrooms
3
baths
8
guests
4.8
(25)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
A beautifully renovated four-bedroom, three-bath golf course home in the gated oceanfront resort of Palmetto Dunes.
Upon entry, be invited into the living room with a view of the pristine fairway of the George Fazio Golf Course. Separating the living room a
7 Ginger Beer | Fairway Breeze
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House -
$256.00 - $796.00 / per night
4
bedrooms
3
baths
9
guests
4.9
(13)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer’s tee shot? Is the contact between the driver and the golf ball making the sweetest sou
42 Stoney Creek
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House -
$557.00 - $2,599.00 / per night
7
bedrooms
7
baths
1
half bath
15
guests
4.8
(9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Looking for the perfect vacation retreat? You’ve come to the right spot!
This home is completely renovated! The inside of the home has new floors, new light fixtures, a new stairway, a newly updated kitchen with stainless appliances, a new laundry room, and
57 North Sea Pines
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House -
$492.00 - $1,399.00 / per night
5
bedrooms
3
baths
1
half bath
12
guests
5
(12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
You will love this charming three-bedroom, 2.5-bath, two-story home. Total renovations were finished in May 2021.
This home offers a wonderful layout that allows everyone to gather together and spread out. The first floor has a living room with a study area
2 Azalea
House -
$144.00 - $2,278.00 / per night
3
bedrooms
2
baths
1
half bath
10
guests
5
(4)
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
32 Bradley Beach Road
House -
$180.00 - $557.00 / per night
3
bedrooms
3
baths
9
guests
5
(10)
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