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

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Guest favourite
Home in Shipyard
Private Pool | Golf | Exq. Coffee | Seascape
4 bedrooms, 5 beds, 3 private bathrooms
19–24 Oct
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4.93 out of 5 average rating, 44 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, 123 reviews
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Guest favourite
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Townhouse in Hilton Head Island
Courtside 77
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 4 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
17–22 Oct
4.9 out of 5 average rating, 104 reviews
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Guest favourite
Apartment in Palmetto Dunes
Spacious Villa in Hilton Head Resort! STR#024945
2 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.94 out of 5 average rating, 149 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
8–13 Nov
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Home in Hilton Head Island
Oceanfront 8BR Home | 8 Suites | Pool | Sleeps 16+
8 bedrooms, 14 beds, 7.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Hilton Head Island
Beautiful villa in Hilton Head South Carolina!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Flat in Hilton Head Island
Coastal Charm! Across from Coligny Beach!
2 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 15 reviews
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Superhost
Home in Sea Pines
Hidden Sea Pines Gem | Pool, Spa, Pet Friendly
4 bedrooms, 8 beds, 3.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Oct
4.98 out of 5 average rating, 87 reviews
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Guest favourite
Villa in Hilton Head Island
Surf Court 45
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Shipyard
The Caddyshack - Perfect Location!
2 bedrooms, 3 beds, 2.5 bathrooms
5–10 Oct
4.99 out of 5 average rating, 75 reviews
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Top guest favourite
Apartment in Hilton Head Island
Beachside Hilton Head Villa Fully Renovated
2 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.95 out of 5 average rating, 148 reviews
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Top guest favourite
Flat in Hilton Head Island
Top Floor Beach Villa Best in HH
2 bedrooms, 3 beds, 2 bathrooms
17–22 Oct
4.97 out of 5 average rating, 71 reviews
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Guest favourite
Villa in Hilton Head Island
Steps from the beach Large pool, family friendly
1 bedroom, 1 bed, 1 bathroom
1–6 Nov
4.83 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Hilton Head Island
Large home, beach close, pool
6 bedrooms, 16 beds, 4 bathrooms
16–21 Oct
4.94 out of 5 average rating, 238 reviews
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Top guest favourite
Home in Sea Pines
Sea Pines Home w Large Deck | Great for Couples!
3 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 34 reviews