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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 Luxury! KING BED Beach Bar & Pickleball
1 bedroom, 2 beds, 1 private bathroom
28 Sept – 3 Oct
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4.97 out of 5 average rating, 238 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 Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 5 reviews
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Superhost
Apartment in Palmetto Dunes
Lagoon View Villa in Palmetto Dunes
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Villa in Hilton Head Island
Steps from the beach Large pool, family friendly
1 bedroom, 1 bed
1–6 Nov
4.83 out of 5 average rating, 29 reviews
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Top guest favourite
Flat in Palmetto Dunes
Incredible Hilton Head condo - private beach!
2 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 14 reviews
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Townhouse in Hilton Head Island
Surf Court 66
2 bedrooms, 3 beds
17–22 Sept
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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, 74 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
Home in Hilton Head Island
Family Retreat | 1 Min to Beach | Pool Spa Theater
6 bedrooms, 12 beds
5–10 Oct
5.0 out of 5 average rating, 15 reviews
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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
Flat in Hilton Head Island
*Cute, comfy, clean* 5 min walk to toes in sand!
3 bedrooms, 6 beds
18–23 Oct
4.97 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Sea Pines
Sea Pines Home w Large Deck | Great for Couples!
3 bedrooms, 3 beds
16–21 Oct
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds
17–22 Sept
4.98 out of 5 average rating, 87 reviews
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Guest favourite
Treehouse in Sea Pines
2031 Deer Island Treehouse - Walk to Harbour Town
2 bedrooms, 3 beds
18–23 Sept
4.85 out of 5 average rating, 75 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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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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Superhost
Apartment in Hilton Head Island
Hilton Head Beach and Tennis TV F18
2 bedrooms, 4 beds
17–22 Sept