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

Top guest favourite
Chalet in Hilton Head Island
180º Ocean Views, Treehouse "Siren's Lookout"
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Sept
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4.98 out of 5 average rating, 118 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, 118 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
Luxe
Home in Hilton Head Island
8 Gull Point, Sea Pines: Marsh-Front, Private Pool
4 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
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, 32 reviews
Superhost
Home in Hilton Head Island
Chic Sea Pines Retreat w Lagoon Views | Sleeps 6
3 bedrooms, 3 king beds, 2.5 bathrooms
8–13 Aug
Guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
4 bedrooms, 7 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Hilton Head Island
Hilton Ivory by AvantStay | Luxe Home + Pool/Patio
6 bedrooms, 10 beds, 4.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Hilton Head Island
Charming , cozy apartment near the beach ….
1 bedroom, 1 king bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 40 reviews
Superhost
Home in Hilton Head Island
Private Pool Retreat | One Level | 2 Living Areas
3 bedrooms, 3 king beds, 3 bathrooms
10–15 Aug
New place to stay
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
Guest favourite
Home in Hilton Head Island
Private Pool ~ Cabana ~ 5 Deer Run Lane
3 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
4.89 out of 5 average rating, 18 reviews
Luxe
Villa in Hilton Head Island
1465 Sound Villas, Sea Pines: Beachfront Luxury
4 bedrooms, 5 beds, 5 bathrooms
8–13 Aug
Guest favourite
Home in Hilton Head Island
Modern Home ~ Golf Course Views ~ .8 Mile to Beach
4 bedrooms, 5 beds, 3 bathrooms
8–13 Aug
5.0 out of 5 average rating, 18 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
Guest favourite
Home in Hilton Head Island
Pink Sand Paradise - A Peaceful Luxury Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Townhouse in Hilton Head Island
Beachfront Resort 2B Golf Beach Pickleball Tennis
2 bedrooms, 6 beds, 2 bathrooms
13–18 Aug
4.96 out of 5 average rating, 158 reviews
Apartment in Hilton Head Island
The Salty Mermaid
2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
New place to stay
Superhost
Home in Hilton Head Island
MyStay at 14 Laughing Gull - 7BR Oceanfront Estate
7 bedrooms, 11 beds, 8 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews