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

Top guest favourite
Townhouse in Hilton Head Island
Beachfront Resort 2b Golf Lagoon Pickleball Tennis
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Jul
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4.98 out of 5 average rating, 164 reviews
Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
5.0 out of 5 average rating, 118 reviews, 6 bedrooms, 15 beds, 4 bathrooms
23–28 Aug
Superhost
Home in Hilton Head Island
Pet-Friendly, South Beach Pool Access, 3BR
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Treehouse in Hilton Head Island
Luxury Waterfront Tree House | Harbour Town | Pool
5.0 out of 5 average rating, 32 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
Home in Hilton Head Island
Luxury 2nd Row Beach Estate | 6BR | Pool Sleeps 12
New place to stay, 6 bedrooms, 7 beds, 6.5 bathrooms
4–11 Jul
Luxe
Home in Hilton Head Island
74 Baynard Cove, Sea Pines: Pvt Pool, Fenced Yard
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 10 beds, 4 bathrooms
7–12 Sept
Luxe
Home in Hilton Head Island
8 Gull Point, Sea Pines: Marsh-Front, Private Pool
4 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
Home in Hilton Head Island
Hilton Head Retreat
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
13–18 Jul
Superhost
Guest house in Bluffton
Cozy Carriage House Under Oaks | Old Town Bluffton
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
Luxe
Flat in Hilton Head Island
1875 Beachside Tennis: Stunning Views, Wildlife
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Superhost
Home in Hilton Head Island
Chic Sea Pines Retreat w Lagoon Views | Sleeps 6
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Aug
Superhost
Home in Hilton Head Island
Private Pool Retreat | One Level | 2 Living Areas
New place to stay, 3 bedrooms, 3 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
4.99 out of 5 average rating, 81 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
Superhost
Villa in Hilton Head Island
Charming bay view villa with pool, washer/dryer, b
2 bedrooms, 3 beds, 2.5 bathrooms
12–17 Sept
Guest favourite
Home in Hilton Head Island
Starfish Beach House with Pool and Bikes
4.92 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
Superhost
Flat in Hilton Head Island
Near Beach|Pool| Pickleball| WaterView|Island Club
New place to stay, 1 bedroom, 2 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Home in Hilton Head Island
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
Superhost
Villa in Hilton Head Island
Snowbird/dog-friendly villa with WiFi, 2 patios, &
2 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
Luxe
Home in Hilton Head Island
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