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

Top guest favourite
Treehouse in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds, 2 private bathrooms
15–20 Sept
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4.98 out of 5 average rating, 101 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, 122 reviews
Top guest favourite
Apartment in Hilton Head Island
The Lookout - A Modern Beach Retreat (Oceanfront)
1 bedroom, 4 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Apartment in Hilton Head Island
Ocean View & Steps to Beach! Remodeled HHBT Condo!
1 bedroom, 4 beds, 1 bathroom
15–20 Nov
4.96 out of 5 average rating, 375 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
Top guest favourite
Villa in Sea Pines
HHI South Forest beach/WLK TO BEACH, dining, pool
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 105 reviews
Guest favourite
Apartment in Hilton Head Island
Whispering Tides II
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 16 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
Villa in Hilton Head Island
Surf Court 45
3 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Palmetto Dunes
Walk to Ocean | Pool | Large Bedrooms | Sea’Esta
2 bedrooms, 4 queen beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 151 reviews
Guest favourite
Home in Hilton Head Island
The Beachfront Estate at 5 Alder Lane
6 bedrooms, 11 beds, 5 bathrooms
20–27 Sept
4.95 out of 5 average rating, 22 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
Top guest favourite
Apartment in Hilton Head Island
Relaxing Coastal Retreat w/ Pools + Beach <1/4mi
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Hilton Head Island
Oceanfront 8BR Home | 8 Suites | Pool | Sleeps 16+
8 bedrooms, 14 beds, 7.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Apartment in Hilton Head Island
Heron's Haven on Port Royal Sound, 2BR/2BA
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.95 out of 5 average rating, 241 reviews
Guest favourite
Flat in Shelter Cove
Marriott Harbour Point - 2BD
2 bedrooms, 3 beds, 2 bathrooms
17–22 Nov
4.84 out of 5 average rating, 57 reviews
Top guest favourite
Apartment in Palmetto Dunes
Sea Gem - Winter Sunshine by the Sea
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.94 out of 5 average rating, 143 reviews
Guest favourite
Townhouse in Shipyard
Beachfront Resort 2B Golf Beach Pool Pickleball
2 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
4.96 out of 5 average rating, 169 reviews
Guest favourite
Flat in Hilton Head Island
Beach Haven | Quiet Corner | Easy Beach Access
1 bedroom, 2 beds, No bathroom
20–25 Sept
5.0 out of 5 average rating, 7 reviews