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

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Top guest favourite
Home in Hilton Head Island
Resort-Style Pool, Cute House 88 Steps to Sand
3 bedrooms, 5 beds, 3 private bathrooms
10–15 Oct
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4.97 out of 5 average rating, 136 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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Home in Hilton Head Island
Beautiful villa in Hilton Head South Carolina!
2 bedrooms, 3 beds
1–6 Oct
New place to stay
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Top guest favourite
Villa in Palmetto Dunes
Spacious dog-friendly villa, walk to the beach
3 bedrooms, 6 beds
17–22 Oct
4.9 out of 5 average rating, 104 reviews
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Guest favourite
Home in Palmetto Dunes
Private Pool, Lagoon View, & Walk to Beach!
3 bedrooms, 6 beds
18–23 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Treehouse in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds
1–6 Oct
4.98 out of 5 average rating, 103 reviews
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Guest favourite
Home in Hilton Head Island
Oceanfront 8BR Home | 8 Suites | Pool | Sleeps 16+
8 bedrooms, 14 beds
19–24 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Palmetto Dunes
Palmetto Dunes Beach House
3 bedrooms, 5 beds
16–21 Oct
5.0 out of 5 average rating, 21 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, 59 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
Apartment in Hilton Head Island
Relaxing Coastal Retreat w/ Pools + Beach <1/4mi
2 bedrooms, 3 beds
19–24 Oct
4.93 out of 5 average rating, 15 reviews
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Superhost
Villa in Hilton Head Island
Beachside Villa with Pool, Steps to the Sand
3 bedrooms, 4 beds
24–29 Oct
New place to stay
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Top guest favourite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
2 bedrooms, 3 beds
22–27 Nov
5.0 out of 5 average rating, 26 reviews
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Superhost
Apartment in Hilton Head Island
Stunning 3 BR Oceanfront Retreat at 221 Shorewood
3 bedrooms, 4 beds
6–11 Oct
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Top guest favourite
Guest suite in Hilton Head Island
'Under the Oaks' on Hilton Head - Walk to Beach
2 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Hilton Head Island
Walk to Beach-Amazing New Home-Hot Tub-Heated Pool
6 bedrooms, 11 beds
15–20 Nov
5.0 out of 5 average rating, 104 reviews
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Guest favourite
Flat in Sea Pines
Great Find! Walk to Beach, Golf & Dining!
2 bedrooms, 4 beds
5–10 Oct
4.88 out of 5 average rating, 56 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, 76 reviews