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

Top guest favourite
Chalet in Sea Pines
180º Ocean Views, Treehouse "Siren's Lookout"
2 bedrooms, 3 beds, 2 private bathrooms
16–21 Aug
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4.98 out of 5 average rating, 118 reviews
Top guest favourite
Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 32 reviews
Flat in Sea Pines
Steps to the beach and the Salty Dog!
2 bedrooms, 3 beds
24–29 Jul
Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds
23–28 Aug
5.0 out of 5 average rating, 117 reviews
Home in Hilton Head Island
Hilton Head Retreat
2 bedrooms, 2 beds
25–30 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
4 bedrooms, 7 beds
15–20 Dec
5.0 out of 5 average rating, 8 reviews
Superhost
Apartment in Hilton Head Island
Bluewater Resort & Marina - Large 3BR/3BA
3 bedrooms, 5 beds
19–26 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Sea Pines
Sea Pines house ~ Golf Sim / Putting Green / Games
4 bedrooms
23–28 Jul
5.0 out of 5 average rating, 87 reviews
Guest favourite
Home in Sea Pines
Modern Home ~ Golf Course Views ~ .8 Mile to Beach
4 bedrooms, 5 beds
5–10 Jul
5.0 out of 5 average rating, 18 reviews
Superhost
Home in Sea Pines
Chic Sea Pines Retreat w Lagoon Views | Sleeps 6
3 bedrooms, 3 king beds
8–13 Aug
Luxe
Home in Hilton Head Island
Private Island in Hilton Head, Events & Poolside
8 bedrooms, 15 beds
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Hilton Head Island
Coastal Calm: Lagoon View, Beach, Family Friendly
2 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 27 reviews
Luxe
Home in Sea Pines
8 Gull Point, Sea Pines: Marsh-Front, Private Pool
4 bedrooms, 5 beds
17–22 Jul
Top guest favourite
Home in Shipyard
Walk to Beach | Golf | Pool | Private | Shipyard
3 bedrooms, 4 beds
22–27 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds
23–28 Aug
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Apartment in Hilton Head Island
Ocean Front Resort Condo
1 bedroom, 4 beds
4–9 Oct
4.99 out of 5 average rating, 438 reviews
Flat in Palmetto Dunes
Lagoon and Links Escape
1 bedroom, 2 beds
10–15 Aug
Superhost
Home in Hilton Head Island
Oceanfront Pool, Balcony + Stunning Atlantic Views
5 bedrooms, 6 beds
23–28 Aug
New place to stay
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds
17–22 Jul
New place to stay