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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
Beach condo with pool and stunning nature views
2 bedrooms, 3 beds, 2 private bathrooms
17–24 Oct
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4.99 out of 5 average rating, 147 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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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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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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Home in Hilton Head Island
The Beachfront Estate at 5 Alder Lane
6 bedrooms, 11 beds, 5 bathrooms
20–27 Sept
4.95 out of 5 average rating, 22 reviews
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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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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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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
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Villa in Sea Pines
HHI South Forest beach/WLK TO BEACH, dining, pool
2 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.98 out of 5 average rating, 104 reviews
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Apartment in Hilton Head Island
Beachside Hilton Head Villa Fully Renovated
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 145 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, 403 reviews
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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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Apartment in Palmetto Dunes
Spacious Villa in Hilton Head Resort! STR#024945
2 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.94 out of 5 average rating, 145 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, 101 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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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, 40 reviews
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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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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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Flat in Hilton Head Island
2BR Dunes VIlla - Pool
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews