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

Top guest favourite
Home in Sea Pines
“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops
3 bedrooms, 4 beds, 2 shared bathrooms
31 Aug – 5 Sept
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4.99 out of 5 average rating, 150 reviews
Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
5.0 out of 5 average rating, 119 reviews, 6 bedrooms, 15 beds, 4 bathrooms
23–28 Aug
Superhost
Home in Sea Pines
Pet-Friendly, South Beach Pool Access, 3BR
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Home in Sea Pines
Two Fawns at Sea Pines|4+BR|New Pool/Spa!
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 7 beds, 3 bathrooms
2–7 Dec
Home in Hilton Head Island
Hilton Head Retreat
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Jul
Superhost
Home in Sea Pines
Spacious, Renovated House with Private Spa and Pri
3 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
Home in Hilton Head Island
Charming remodeled 4th row House walk to Beach !
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
Luxe
Home in Sea Pines
29 South Beach, Sea Pines: Pool, Walk to Beach
4 bedrooms, 4 beds, 4.5 bathrooms
11–16 Jul
Top guest favourite
Home in Hilton Head Island
Dove's Nest - New Pool&Spa! Steps to beach&dining
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
Luxe
Home in Sea Pines
Private Pool & Spa | Secluded | in Heritage Woods
5.0 out of 5 average rating, 47 reviews, 5 bedrooms, 8 beds, 5 bathrooms
16–21 Aug
Top guest favourite
Home in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
4.98 out of 5 average rating, 94 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
Apartment in Hilton Head Island
Ocean One 511
2 bedrooms, 2 beds, 2 bathrooms
13–18 Aug
Top guest favourite
Home in Hilton Head Island
Walk to Beach-Amazing New Home-Hot Tub-Heated Pool
5.0 out of 5 average rating, 93 reviews, 6 bedrooms, 11 beds, 4 bathrooms
30 Aug – 4 Sept
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
Superhost
Home in Palmetto Dunes
Luxury Dunes Paradise - Private Pool
New place to stay, 4 bedrooms, 7 beds, 4 bathrooms
6–11 Jul
Top guest favourite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Apartment in Sea Pines
Charming , cozy apartment near the beach ….
5.0 out of 5 average rating, 41 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug