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

Top guest favourite
Chalet in Sea Pines
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
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
New place to stay
Guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
4 bedrooms, 7 beds, 3 bathrooms
15–20 Dec
5.0 out of 5 average rating, 8 reviews
Luxe
Home in Sea Pines
8 Gull Point, Sea Pines: Marsh-Front, Private Pool
4 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
Top guest favourite
Home in Shipyard
The Caddyshack - Perfect Location!
2 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Apartment in Hilton Head Island
Beachside Hilton Head Villa Fully Renovated
2 bedrooms, 4 beds, 2 bathrooms
31 Jul – 5 Aug
4.96 out of 5 average rating, 140 reviews
Top guest favourite
Flat in Hilton Head Island
Top Floor Beach Villa Best in HH
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 58 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
Superhost
Treehouse in Sea Pines
Waterfront Tree House | HT Pool | Private Office
3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Hilton Head Island
Hilton Head Hidden Gem
2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
4.89 out of 5 average rating, 209 reviews
Flat in Hilton Head Island
Sun, Sand, and Sea — Right Outside Your Door
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Hilton Head Island
Coligny Area- 3 Bedroom Villa
3 bedrooms, 5 beds, 3.5 bathrooms
28 Aug – 2 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Apartment in Sea Pines
Island Serenity; Escape life, relax, and unwind.
2 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Shipyard
Walk to Beach | Golf | Pool | Private | Shipyard
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Palmetto Dunes
Walk to Ocean | Pool | Large Bedrooms | Sea’Esta
2 bedrooms, 4 queen beds, 2 bathrooms
20–25 Jul
4.99 out of 5 average rating, 145 reviews
Guest favourite
Flat in Hilton Head Island
*Cute, comfy, clean* 5 min walk to toes in sand!
3 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Villa in Hilton Head Island
Walk to Beach | Lagoon View | 2 Kings+Queen & Bunk
3 bedrooms, 5 beds, 3.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 106 reviews
Home in Palmetto Dunes
Luxury 2nd Row Beach Estate | 6BR | Pool Sleeps 12
6 bedrooms, 7 beds, 6.5 bathrooms
4–11 Jul
New place to stay