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

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Superhost
Apartment in Hilton Head Island
PR Sound Beach+ POOL Views | Coastal Cottage Charm
2 bedrooms, 4 beds, 2 private bathrooms
7–12 Sept
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4.71 out of 5 average rating, 34 reviews
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Top guest favourite
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, 37 reviews
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Apartment in Hilton Head Island
Beautiful Oceanfront Condo at Island Club
2 bedrooms, 3 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 28 reviews
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Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds, 4 bathrooms
8–13 Nov
5.0 out of 5 average rating, 122 reviews
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Top guest favourite
Apartment in Shipyard
202 Beachwalk 3BR/3.5BA Villa 10min Walk to Beach
3 bedrooms, 6 beds, 3.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Sea Pines
“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
4.99 out of 5 average rating, 157 reviews
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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, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Apartment in Hilton Head Island
Beach condo in gated resort w/ tons of amenities!
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.91 out of 5 average rating, 195 reviews
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Home in Palmetto Dunes
Palmetto Dunes Beach House
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 reviews
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Home in Sea Pines
Sea Pines house ~ Golf Sim / Putting Green / Games
4 bedrooms, 4 bathrooms
16–21 Sept
5.0 out of 5 average rating, 94 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, 1 bathroom
15–20 Nov
4.96 out of 5 average rating, 375 reviews
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Townhouse in Hilton Head Island
Courtside 77
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
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Guest favourite
Apartment in Shelter Cove
Marriott Sunset Pointe - 2BD
2 bedrooms, 3 beds, 2 bathrooms
12–17 Dec
4.97 out of 5 average rating, 32 reviews
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Townhouse in Hilton Head Island
Piece of Paradise on Hilton Head Island
2 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
4.92 out of 5 average rating, 168 reviews
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Apartment in Palmetto Dunes
MyStay at 789 Queen's Grant -Pets Ok + Pool, Beach
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Sea Pines
Two Fawns at Sea Pines|4+BR|New Pool/Spa!
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Home in Hilton Head Island
Walk2Beach~Pool~Putting Green~Fenced Yard~EV
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 68 reviews
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Top guest favourite
Home in Shipyard
HHI Escape - Beach Access, Golf Course, Pickleball
2 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 41 reviews
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Villa in Palmetto Dunes
Spacious dog-friendly villa, walk to the beach
3 bedrooms, 6 beds, 2.5 bathrooms
5–10 Sept
4.9 out of 5 average rating, 102 reviews