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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
5.0 out of 5 average rating, 118 reviews, 6 bedrooms, 15 beds, 4 bathrooms
23–28 Aug
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Villa in Hilton Head Island
Steps from the beach Large pool, family friendly
4.93 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug
Top guest favourite
Flat in Hilton Head Island
Top Floor Beach Villa Best in HH
4.97 out of 5 average rating, 58 reviews, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
Guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 7 beds, 3 bathrooms
19–24 Sept
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
Apartment in Hilton Head Island
Beachside Hilton Head Villa Fully Renovated
4.96 out of 5 average rating, 140 reviews, 2 bedrooms, 4 beds, 2 bathrooms
31 Jul – 5 Aug
Top guest favourite
Apartment in Sea Pines
Island Serenity; Escape life, relax, and unwind.
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
Superhost
Treehouse in Sea Pines
Waterfront Tree House | HT Pool | Private Office
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Jul
Top guest favourite
Home in Shipyard
The Caddyshack - Perfect Location!
5.0 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
Top guest favourite
Home in Palmetto Dunes
Palmetto Dunes Gem!
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
10–15 Jul
Flat in Hilton Head Island
Sun, Sand, and Sea — Right Outside Your Door
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Apartment in Hilton Head Island
Hilton Head Hidden Gem
4.89 out of 5 average rating, 209 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Apartment in Palmetto Dunes
Sea Gem - A Cozy Hilton Head Beach Escape
4.93 out of 5 average rating, 132 reviews, 2 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
Top guest favourite
Home in Shipyard
Walk to Beach | Golf | Pool | Private | Shipyard
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Guest favourite
Flat in Hilton Head Island
*Cute, comfy, clean* 5 min walk to toes in sand!
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
23–28 Aug
Top guest favourite
Apartment in Palmetto Dunes
Walk to Ocean | Pool | Large Bedrooms | Sea’Esta
4.99 out of 5 average rating, 145 reviews, 2 bedrooms, 4 beds, 2 bathrooms
20–25 Jul