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

Guest favourite
Apartment in Hilton Head Island
Beach Resort, pools, tennis, pickle ball Tiki bar!
2 bedrooms, 4 beds, 2 private bathrooms
23–28 Aug
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4.86 out of 5 average rating, 159 reviews
Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 119 reviews
Guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
4 bedrooms, 7 beds, 3 bathrooms
2–7 Dec
5.0 out of 5 average rating, 9 reviews
Superhost
Guest house in Bluffton
Cozy Carriage House Under Oaks | Old Town Bluffton
1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Hilton Head Island
Pet-Friendly, South Beach Pool Access, 3BR
3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
New place to stay
Home in Hilton Head Island
Two Fawns at Sea Pines|4+BR|New Pool/Spa!
4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Home in Hilton Head Island
Hilton Head Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Home in Hilton Head Island
Dove's Nest - New Pool&Spa! Steps to beach&dining
4 bedrooms, 9 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Hilton Head Island
Luxury Dunes Paradise - Private Pool
4 bedrooms, 7 beds, 4 bathrooms
6–11 Jul
New place to stay
Superhost
Home in Hilton Head Island
Spacious, Renovated House with Private Spa and Pri
3 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
Luxe
Home in Hilton Head Island
29 South Beach, Sea Pines: Pool, Walk to Beach
4 bedrooms, 4 beds, 4.5 bathrooms
11–16 Jul
Luxe
Home in Hilton Head Island
Private Pool & Spa | Secluded | in Heritage Woods
5 bedrooms, 8 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Hilton Head Island
Walk to Beach-Amazing New Home-Hot Tub-Heated Pool
6 bedrooms, 11 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Treehouse in Hilton Head Island
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Hilton Head Island
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 12 reviews
Home in Hilton Head Island
Charming remodeled 4th row House walk to Beach !
4 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
New place to stay
Flat in Hilton Head Island
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
New place to stay