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

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Guest favourite
Flat in Hilton Head Island
Seaside Villas Escape full condo 1 bedroom + bunks
1 bedroom, 3 beds, 1 private bathroom
24–29 Oct
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4.97 out of 5 average rating, 36 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
Flat in Shelter Cove
Marriott Harbour Point - 2BD
2 bedrooms, 3 beds, 2 bathrooms
6–11 Dec
4.84 out of 5 average rating, 57 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 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
Villa in Sea Pines
HHI South Forest beach/WLK TO BEACH, dining, pool
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 105 reviews
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Top guest favourite
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
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Top guest favourite
Flat in Hilton Head Island
*Cute, comfy, clean* 5 min walk to toes in sand!
3 bedrooms, 6 beds, 2.5 bathrooms
14–19 Oct
4.97 out of 5 average rating, 58 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 Palmetto Dunes
Oceanside Resort - Private Beach Access - 3 Pools
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 117 reviews
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Top guest favourite
Apartment in Hilton Head Island
Ocean View! Remodeled! Steps to beach/Pool/Bar
1 bedroom, 4 beds, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 316 reviews
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Top guest favourite
Apartment in Palmetto Dunes
Walk to Ocean | Pool | Large Bedrooms | Sea’Esta
2 bedrooms, 4 queen beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 151 reviews
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Top guest favourite
Apartment in Hilton Head Island
Hilton Head Hidden Gem
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.9 out of 5 average rating, 216 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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Apartment in Hilton Head Island
Steps to Beach Pool Tennis Pickleball 2 ba/2 bedrm
2 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 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
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Guest favourite
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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Guest favourite
Home in Shipyard
Shipyard Golf: Where Family Memories Shine!
3 bedrooms, 4 beds, 3 bathrooms
24–29 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Apartment in Palmetto Dunes
Sea Gem - A Cozy Hilton Head Beach Escape
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.94 out of 5 average rating, 143 reviews