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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
Gorgeous villa, private beach access, HH Resort
2 bedrooms, 4 beds, 2 private bathrooms
7–12 Oct
,
4.86 out of 5 average rating, 336 reviews
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Guest favourite
Home in Palmetto Dunes
Palmetto Dunes Beach House
3 bedrooms, 5 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 21 reviews
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Villa in Shipyard
Entire Villa in the Greens, Hilton Head Island
2 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
New place to stay
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Flat in Palmetto Dunes
Brand new listing! Clean, remodeled coastal condo
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Treehouse in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.98 out of 5 average rating, 103 reviews
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Apartment in Hilton Head Island
Condo w/ pool - Walk to the beach
2 bedrooms, 4 beds, 1 bathroom
14–19 Oct
4.86 out of 5 average rating, 7 reviews
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Guest favourite
Treehouse in Sea Pines
CoCo's Island Treehouse
2 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.91 out of 5 average rating, 79 reviews
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Guest favourite
Flat in Shelter Cove
Marriott Harbour Point - 2BD
2 bedrooms, 3 beds, 2 bathrooms
9–14 Dec
4.85 out of 5 average rating, 59 reviews
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Guest favourite
Home in Sea Pines
Luxury Sea Pines Home, Lagoon Views on Hilton Head
3 bedrooms, 6 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Apartment in Sea Pines
Island Serenity; Escape life, relax, and unwind.
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
5.0 out of 5 average rating, 41 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 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
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Home in Palmetto Dunes
2-story house with private heated outdoor pool, st
3 bedrooms, 6 beds, 3 bathrooms
26 Oct – 2 Nov
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Top guest favourite
Flat in Hilton Head Island
Ocean Front Condo w/ Private Water Front Balcony
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.98 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, 124 reviews
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Top guest favourite
Home in Sea Pines
Modern Sea Pines: Pet-Friendly, Beach, Bikes
2 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Shipyard
Inquire for Snowbird Rates! Pool, mins to Ocean.
3 bedrooms, 3 beds, 2 bathrooms
9–16 Oct
4.89 out of 5 average rating, 76 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, 76 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, 88 reviews