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

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Top guest favourite
Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds, 2 private bathrooms
26 Sept – 1 Oct
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5.0 out of 5 average rating, 38 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
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, 378 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, 2.5 bathrooms
7–12 Oct
4.97 out of 5 average rating, 58 reviews
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Guest favourite
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Apartment in Palmetto Dunes
Sea Gem - Winter Sunshine by the Sea
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.94 out of 5 average rating, 146 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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Top guest favourite
Home in Shipyard
The Caddyshack - Perfect Location!
2 bedrooms, 3 beds, 2.5 bathrooms
24–29 Oct
4.99 out of 5 average rating, 75 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, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 34 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 bathroom
1–6 Nov
4.83 out of 5 average rating, 29 reviews
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Guest favourite
Villa in Hilton Head Island
Surf Court 45
3 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 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, 4 bathrooms
8–13 Nov
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Villa in Palmetto Dunes
Walk to the Beach, One Level Villa, COMFY beds
2 bedrooms, 3 beds, 2 bathrooms
4–9 Dec
4.91 out of 5 average rating, 141 reviews
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Guest favourite
Apartment in Hilton Head Island
Condo w/ pool - Walk to the beach
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Hilton Head Island
Newly Renovated; 3.5 Acres Private Waterfront
3 bedrooms, 8 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 18 reviews
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Top guest favourite
Flat in Hilton Head Island
2BR Dunes VIlla - Pool
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Townhouse in Hilton Head Island
Piece of Paradise on Hilton Head Island
2 bedrooms, 5 beds, 1.5 bathrooms
11–16 Oct
4.92 out of 5 average rating, 171 reviews
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Townhouse in Hilton Head Island
Surf Court 66
2 bedrooms, 3 beds, 2.5 bathrooms
19–24 Sept
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Guest favourite
Home in Hilton Head Island
Oceanfront 8BR Home | 8 Suites | Pool | Sleeps 16+
8 bedrooms, 14 beds, 7.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews