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Search results; Over 1,000 homes in Hilton Head Island

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Apartment in Sea Pines
Serene Hilton Head Island Condo w/ Community Pool!
2 bedrooms, 3 beds, 2.5 private bathrooms
27 Sept – 2 Oct
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4.78 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds
8–13 Nov
5.0 out of 5 average rating, 123 reviews
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Top guest favourite
Apartment in Hilton Head Island
Ocean View & Steps to Beach! Remodeled HHBT Condo!
1 bedroom, 4 beds
15–20 Nov
4.96 out of 5 average rating, 378 reviews
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Guest favourite
Flat in Hilton Head Island
*Cute, comfy, clean* 5 min walk to toes in sand!
3 bedrooms, 6 beds
7–12 Oct
4.97 out of 5 average rating, 58 reviews
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Top guest favourite
Apartment in Palmetto Dunes
Sea Gem - Winter Sunshine by the Sea
2 bedrooms, 3 beds
21–26 Sept
4.94 out of 5 average rating, 146 reviews
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Guest favourite
Flat in Hilton Head Island
Coastal Charm! Across from Coligny Beach!
2 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Apartment in Hilton Head Island
Relaxing Coastal Retreat w/ Pools + Beach <1/4mi
2 bedrooms, 3 beds
20–25 Sept
4.93 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Apartment in Hilton Head Island
Lovely Beachside Villa w/ Resort Amenities
2 bedrooms, 5 beds
17–22 Oct
4.95 out of 5 average rating, 115 reviews
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Top guest favourite
Home in Shipyard
The Caddyshack - Perfect Location!
2 bedrooms, 3 beds
5–10 Oct
4.99 out of 5 average rating, 75 reviews
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Townhouse in Hilton Head Island
Surf Court 66
2 bedrooms, 3 beds
21–26 Sept
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Guest favourite
Villa in Hilton Head Island
Surf Court 45
3 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Apartment in Hilton Head Island
1st Floor, 8 Min Walk Beach, King Bed, In Unit W/D
2 bedrooms, 3 beds
24–29 Oct
4.98 out of 5 average rating, 133 reviews
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Guest favourite
Home in Hilton Head Island
Oceanfront 8BR Home | 8 Suites | Pool | Sleeps 16+
8 bedrooms, 14 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Flat in Hilton Head Island
2BR Dunes VIlla - Pool
2 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 11 reviews
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Townhouse in Hilton Head Island
Courtside 77
2 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Hilton Head Island
Family Retreat | 1 Min to Beach | Pool Spa Theater
6 bedrooms, 12 beds
8–13 Nov
5.0 out of 5 average rating, 15 reviews
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Superhost
Apartment in Palmetto Dunes
Lagoon View Villa in Palmetto Dunes
3 bedrooms, 4 beds
12–17 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Townhouse in Hilton Head Island
Piece of Paradise on Hilton Head Island
2 bedrooms, 5 beds
11–16 Oct
4.92 out of 5 average rating, 172 reviews