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

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Guest favourite
Townhouse in Hilton Head Island
Luxury 3-Bdrm HHI Art Loft (STR Permit #07700)
3 bedrooms, 4 beds, 2.5 private bathrooms
3–8 Oct
,
4.92 out of 5 average rating, 144 reviews
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Guest favourite
Home in Palmetto Dunes
Palmetto Dunes Beach House
3 bedrooms, 5 beds
16–21 Oct
5.0 out of 5 average rating, 21 reviews
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Flat in Palmetto Dunes
Brand new listing! Clean, remodeled coastal condo
2 bedrooms, 3 beds
1–6 Oct
New place to stay
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Guest favourite
Home in Sea Pines
Canopy House | Walk to Harbour Town | Marshfront
2 bedrooms, 3 beds
3–8 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Apartment in Hilton Head Island
Condo w/ pool - Walk to the beach
2 bedrooms, 4 beds
14–19 Oct
4.86 out of 5 average rating, 7 reviews
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Top guest favourite
Apartment in Sea Pines
Island Serenity; Escape life, relax, and unwind.
2 bedrooms, 3 beds
14–19 Nov
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Flat in Hilton Head Island
Ocean Front Condo w/ Private Water Front Balcony
1 bedroom, 2 beds
1–6 Oct
4.98 out of 5 average rating, 44 reviews
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Home in Palmetto Dunes
2-story house with private heated outdoor pool, st
3 bedrooms, 6 beds
26 Oct – 2 Nov
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Superhost
Home in Sea Pines
Hidden Sea Pines Gem | Pool, Spa, Pet Friendly
4 bedrooms, 8 beds
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Hilton Head Island
Beautiful villa in Hilton Head South Carolina!
2 bedrooms, 3 beds
1–6 Oct
New place to stay
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Top guest favourite
Apartment in Hilton Head Island
Peaceful Retreat at Seascape Villas
1 bedroom, 2 beds
18–23 Oct
5.0 out of 5 average rating, 42 reviews
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Superhost
Apartment in Hilton Head Island
Stunning 3 BR Oceanfront Retreat at 221 Shorewood
3 bedrooms, 4 beds
24–29 Oct
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Top guest favourite
Treehouse in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds
1–6 Oct
4.98 out of 5 average rating, 103 reviews
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Guest favourite
Treehouse in Sea Pines
CoCo's Island Treehouse
2 bedrooms, 5 beds
1–6 Oct
4.91 out of 5 average rating, 79 reviews
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Top guest favourite
Apartment in Hilton Head Island
Island Club Condo: Beach, Pool, Gym, Pickleball
1 bedroom, 4 beds
22–27 Oct
4.92 out of 5 average rating, 103 reviews
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Guest favourite
Flat in Shelter Cove
Marriott Harbour Point - 2BD
2 bedrooms, 3 beds
9–14 Dec
4.85 out of 5 average rating, 59 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, 124 reviews
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Guest favourite
Home in Sea Pines
Luxury Sea Pines Home, Lagoon Views on Hilton Head
3 bedrooms, 6 beds
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Sea Pines
Modern Sea Pines: Pet-Friendly, Beach, Bikes
2 bedrooms, 4 beds
31 Oct – 5 Nov
5.0 out of 5 average rating, 5 reviews