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

Top guest favourite
Apartment in Palmetto Dunes
Sunset Serenity - Luxury on The Lagoon!
2 bedrooms, 4 beds, 2 private bathrooms
23–28 Jul
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4.97 out of 5 average rating, 146 reviews
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, 119 reviews
Top guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
4 bedrooms, 7 beds
2–7 Dec
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Sea Pines
Pet-Friendly, South Beach Pool Access, 3BR
3 bedrooms, 5 beds
2–7 Aug
New place to stay
Luxe
Home in Sea Pines
29 South Beach, Sea Pines: Pool, Walk to Beach
4 bedrooms, 4 beds
11–16 Jul
Home in Hilton Head Island
Charming remodeled 4th row House walk to Beach !
4 bedrooms, 5 beds
7–12 Jul
New place to stay
Top guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds
9–14 Aug
4.99 out of 5 average rating, 81 reviews
Luxe
Villa in Sea Pines
1465 Sound Villas, Sea Pines: Beachfront Luxury
4 bedrooms, 5 beds
8–13 Aug
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds
17–22 Aug
New place to stay
Home in Shipyard
Greenside Haven | Gated, Beach, Golf, Pet-Friendly
3 bedrooms, 8 beds
13–18 Jul
New place to stay
Home in Hilton Head Island
Hilton Head Retreat
2 bedrooms, 2 beds
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Luxe
Home in Sea Pines
Private Pool & Spa | Secluded | in Heritage Woods
5 bedrooms, 8 beds
16–21 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Hilton Head Island
Dove's Nest - New Pool&Spa! Steps to beach&dining
4 bedrooms, 9 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Hilton Head Island
Walk to Beach-Amazing New Home-Hot Tub-Heated Pool
6 bedrooms, 11 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 93 reviews
Superhost
Home in Hilton Head Island
Oceanfront Pool, Balcony + Stunning Atlantic Views
5 bedrooms, 6 beds
8–13 Jul
New place to stay
Superhost
Home in Sea Pines
Spacious, Renovated House with Private Spa and Pri
3 bedrooms, 4 beds
20–25 Sept
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, 33 reviews
Top guest favourite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
2 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Sea Pines
Coastal Chic Retreat Near Beach and Sea Pines.
1 bedroom, 1 king bed
27 Jul – 1 Aug
5.0 out of 5 average rating, 41 reviews