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

Guest favourite
Townhouse in Shipyard
Stylish Tennis-Golf- Beach Retreat-Renovated!
2 bedrooms, 3 beds, 2.5 private bathrooms
8–13 Sept
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4.92 out of 5 average rating, 224 reviews
Guest favourite
Home in Sea Pines
High Cotton in Sea Pines
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Shipyard
202 Beachwalk 3BR/3.5BA Villa 10min Walk to Beach
3 bedrooms, 6 beds, 3.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds, 4 bathrooms
8–13 Nov
5.0 out of 5 average rating, 123 reviews
Guest favourite
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sea Pines
Two Fawns at Sea Pines|4+BR|New Heated Pool/Spa!
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Sea Pines
“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
4.99 out of 5 average rating, 157 reviews
Superhost
Home in Sea Pines
Canopy House | Walk to Harbour Town | Marshfront
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Palmetto Dunes
Luxury Dunes Paradise - Private Pool
4 bedrooms, 7 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Hilton Head Island
Family Retreat | 1 Min to Beach | Pool Spa Theater
6 bedrooms, 12 beds, 4 bathrooms
5–10 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Palmetto Dunes
Luxury Palmetto Dunes Retreat with Private Pool
4 bedrooms, 6 beds, 5 bathrooms
14–19 Sept
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Home in Palmetto Dunes
2 Master Suites, full size pool!
5 bedrooms, 8 beds, 5.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Hilton Head Island
Spacious Deck, Hot Tub, Second Row To Beach & Bra
3 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Sea Pines
Family Memories Are Made Better at Deer Run
3 bedrooms, 4 beds, 3 bathrooms
7–12 Nov
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Hilton Head Island
Luxury Beachside 6BR Coastal Paradise~Pool/Hot Tub
6 bedrooms, 10 beds, 5 bathrooms
4–9 Nov
4.91 out of 5 average rating, 69 reviews
Top guest favourite
Apartment in Hilton Head Island
Relaxing Coastal Retreat w/ Pools + Beach <1/4mi
2 bedrooms, 3 beds, 2 bathrooms
19–24 Oct
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds, 2.5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 87 reviews
Apartment in Hilton Head Island
Shorewood 332
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Home in Hilton Head Island
Walk to Beach-Amazing New Home-Hot Tub-Heated Pool
6 bedrooms, 11 beds, 4 bathrooms
17–22 Oct
5.0 out of 5 average rating, 103 reviews