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

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Top guest favourite
Apartment in Sea Pines
5 Star Location-Harbourtown-Walkable Area
1 bedroom, 2 beds, 1 private bathroom
30 Sept – 5 Oct
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5.0 out of 5 average rating, 127 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, 374 reviews
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Top guest favourite
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, 26 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, 122 reviews
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Top guest favourite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 20 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
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, 22 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, 194 reviews
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Superhost
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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Guest favourite
Home in Hilton Head Island
Luxury Beachside 6BR Coastal Paradise~Pool/Hot Tub
6 bedrooms, 10 beds, 5 bathrooms
4–9 Nov
4.91 out of 5 average rating, 68 reviews
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Superhost
Apartment in Hilton Head Island
MyStay at 136 Shorewood | Ocean+Pool Views in SFB!
2 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Apartment in Palmetto Dunes
Ocean Views at Villamare 1405, Right on the Beach!
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 85 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, 13 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
5–10 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
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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Top guest favourite
Villa in Hilton Head Island
2BR/2.5BA Direct Oceanfront Resort-Great Amenities
2 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 51 reviews
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Top guest favourite
Flat in Hilton Head Island
Luxury 2026 Renovation+Oceanfront Views!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
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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Top guest favourite
Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 38 reviews