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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
Beach condo with pool and stunning nature views
2 bedrooms, 3 beds, 2 private bathrooms
17–24 Oct
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4.99 out of 5 average rating, 148 reviews
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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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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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Apartment in Palmetto Dunes
Ocean View | Top Floor | Walk to Beach | Pools!
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 291 reviews
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Flat in Palmetto Dunes
Incredible Hilton Head condo - private beach!
2 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 11 reviews
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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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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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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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Villa in Hilton Head Island
Modern Oceanfront Villa With Views and Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 146 reviews
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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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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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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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Apartment in Palmetto Dunes
Ocean Views at Villamare 1405, Right on the Beach!
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 86 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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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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Villa in Hilton Head Island
2BR|2.5BA Direct Oceanfront Community-5 Star Rated
2 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 51 reviews
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Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
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Flat in Hilton Head Island
Hilton Head Seaside Vacation Rental
1 bedroom, 1 queen bed, 1 bathroom
14–19 Oct
4.99 out of 5 average rating, 361 reviews
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Apartment in Hilton Head Island
Oceanview Luxury! King Bed 75"TV Pickleball & Bar
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 142 reviews