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

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Top guest favourite
Apartment in Hilton Head Island
Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
1 bedroom, 2 beds, 1 private bathroom
13–18 Oct
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4.98 out of 5 average rating, 368 reviews
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Home in Sea Pines
Canopy House | Walk to Harbour Town | Marshfront
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 4 reviews
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Villa in Palmetto Dunes
Spacious dog-friendly villa, walk to the beach
3 bedrooms, 6 beds, 2.5 bathrooms
17–22 Oct
4.9 out of 5 average rating, 104 reviews
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Superhost
Apartment in Palmetto Dunes
Lagoon View Villa in Palmetto Dunes
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Hilton Head Island
Ocean Front Condo w/ Private Water Front Balcony
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds, 4 bathrooms
8–13 Nov
5.0 out of 5 average rating, 123 reviews
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Top guest favourite
Flat in Hilton Head Island
Beach-themed Corner | Easy Beach Access | Shibumi
1 bedroom, 2 beds, 1 bathroom
9–14 Oct
5.0 out of 5 average rating, 9 reviews
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Home in Hilton Head Island
Beautiful villa in Hilton Head South Carolina!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Apartment in Hilton Head Island
Jim's Direct Oceanfront 3BR Penthouse Villa
3 bedrooms, 5 beds, 3 bathrooms
28 Nov – 3 Dec
4.89 out of 5 average rating, 99 reviews
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Guest favourite
Home in Sea Pines
Oceanfront, Private Beach Access
6 bedrooms, 8 beds, 6.5 bathrooms
10–17 Oct
5.0 out of 5 average rating, 15 reviews
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Superhost
Apartment in Hilton Head Island
Stunning 3 BR Oceanfront Retreat at 221 Shorewood
3 bedrooms, 4 beds, 3 bathrooms
6–11 Oct
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Home in Hilton Head Island
Spacious Deck, Hot Tub, Second Row To Beach & Bra
3 bedrooms, 8 beds, 3 bathrooms
20–25 Oct
5.0 out of 5 average rating, 6 reviews
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Apartment in Palmetto Dunes
Spacious Condo in the Heart of Hilton Head
2 bedrooms, 4 beds, 3 bathrooms
15–20 Oct
4.94 out of 5 average rating, 51 reviews
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Home in Sea Pines
Sea Pines Home w Large Deck | Great for Couples!
3 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Apartment in Hilton Head Island
Oceanfront paradise just steps away to the beach.
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.96 out of 5 average rating, 50 reviews
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Apartment in Palmetto Dunes
Spacious Villa in Hilton Head Resort! STR#024945
2 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.94 out of 5 average rating, 149 reviews
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Apartment in Hilton Head Island
Classic Coastal Condo, Oceanview near Coligny!
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 22 reviews
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Apartment in Sea Pines
Island Serenity; Escape life, relax, and unwind.
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Flat in Hilton Head Island
Just steps to the Beach
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 22 reviews