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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 Luxe KING BED 65TV Beach Bar Pickleball
1 bedroom, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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4.98 out of 5 average rating, 365 reviews
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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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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, 104 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 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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Villa in Hilton Head Island
Surf Court 45
3 bedrooms, 5 beds, 2.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews
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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
4.96 out of 5 average rating, 57 reviews
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Top guest favourite
Apartment in Hilton Head Island
Relaxing Coastal Retreat w/ Pools + Beach <1/4mi
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.92 out of 5 average rating, 13 reviews
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Villa in Hilton Head Island
Direct Ocean Front S. Forest Beach
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.93 out of 5 average rating, 395 reviews
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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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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
Shorewood 207
3 bedrooms, 4 beds, 3 bathrooms
26 Sept – 1 Oct
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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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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
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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Home in Hilton Head Island
W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King beds*grill*gms
4 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.87 out of 5 average rating, 404 reviews
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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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Apartment in Hilton Head Island
Atlantic Views: Your Premier Hilton Head Condo
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.93 out of 5 average rating, 57 reviews
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Villa in Hilton Head Island
Chic Coligny walkable beach villa w/Pool
3 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
5.0 out of 5 average rating, 101 reviews