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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, 128 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, 122 reviews
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Home in Hilton Head Island
Walk2Beach~Pool~Putting Green~Fenced Yard~EV
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 68 reviews
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Guest favourite
Flat in Palmetto Dunes
Incredible Hilton Head condo - private beach!
2 bedrooms, 5 beds
4–9 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Villa in Palmetto Dunes
Spacious dog-friendly villa, walk to the beach
3 bedrooms, 6 beds
5–10 Sept
4.9 out of 5 average rating, 102 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
11–16 Sept
4.98 out of 5 average rating, 104 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
18–23 Sept
4.99 out of 5 average rating, 157 reviews
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Top guest favourite
Home in Shipyard
HHI Escape - Beach Access, Golf Course, Pickleball
2 bedrooms, 4 beds
11–16 Oct
4.98 out of 5 average rating, 41 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, 14 reviews
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Apartment in Hilton Head Island
Steps to Beach Pool Tennis Pickleball 2 ba/2 bedrm
2 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 4 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
14–19 Oct
4.96 out of 5 average rating, 57 reviews
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Guest favourite
Home in Hilton Head Island
The Beachfront Estate at 5 Alder Lane
6 bedrooms, 11 beds
20–27 Sept
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds
9–14 Sept
5.0 out of 5 average rating, 38 reviews
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Top guest favourite
Flat in Shelter Cove
Marriott Harbour Point - 2BD
2 bedrooms, 3 beds
17–22 Nov
4.84 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
14–19 Sept
4.92 out of 5 average rating, 13 reviews
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Guest favourite
Home in Hilton Head Island
Oceanfront 8BR Home | 8 Suites | Pool | Sleeps 16+
8 bedrooms, 14 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Shipyard
The Caddyshack - Perfect Location!
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 72 reviews
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Top guest favourite
Apartment in Hilton Head Island
Renovated Coastal Condo 2.5 Baths- 3 Min to Beach
2 bedrooms, 5 beds
11–16 Dec
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Apartment in Palmetto Dunes
Spacious Villa in Hilton Head Resort! STR#024945
2 bedrooms, 4 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 145 reviews