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

Top guest favourite
Apartment in Hilton Head Island
Beach condo with pool and stunning nature views
2 bedrooms, 3 beds, 2 private bathrooms
17–24 Oct
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4.99 out of 5 average rating, 149 reviews
Top guest favourite
Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds
8–13 Nov
5.0 out of 5 average rating, 123 reviews
Guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds
17–22 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Hilton Head Island
Ocean View & Steps to Beach! Remodeled HHBT Condo!
1 bedroom, 4 beds
15–20 Nov
4.96 out of 5 average rating, 377 reviews
Top guest favourite
Apartment in Hilton Head Island
Relaxing Coastal Retreat w/ Pools + Beach <1/4mi
2 bedrooms, 3 beds
19–24 Oct
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
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Apartment in Hilton Head Island
The Lookout - A Modern Beach Retreat (Oceanfront)
1 bedroom, 4 beds
15–20 Nov
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Villa in Palmetto Dunes
Spacious dog-friendly villa, walk to the beach
3 bedrooms, 6 beds
13–18 Sept
4.9 out of 5 average rating, 104 reviews
Top guest favourite
Home in Hilton Head Island
4BR with Private Pool, Pets Welcome, Steps to Sand
4 bedrooms, 5 beds
13–18 Sept
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in Sea Pines
“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops
3 bedrooms, 4 beds
18–23 Sept
4.99 out of 5 average rating, 157 reviews
Guest favourite
Villa in Hilton Head Island
Surf Court 45
3 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
Superhost
Apartment in Hilton Head Island
Coastal Elegance - Tranquil Beach - Tennis & Pools
2 bedrooms, 4 beds
8–13 Sept
New place to stay
Top guest favourite
Home in Hilton Head Island
W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King beds*grill*gms
4 bedrooms, 5 beds
26 Sept – 1 Oct
4.87 out of 5 average rating, 404 reviews
Guest favourite
Townhouse in Shipyard
Beachfront Resort 2B Golf Beach Pool Pickleball
2 bedrooms, 6 beds
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
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Apartment in Palmetto Dunes
Walk to Ocean | Pool | Large Bedrooms | Sea’Esta
2 bedrooms, 4 queen beds
8–13 Sept
4.99 out of 5 average rating, 152 reviews
Top guest favourite
Home in Sea Pines
SeaPines,2 main suites/screened porch
3 bedrooms, 5 beds
13–18 Sept
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Apartment in Hilton Head Island
Hilton Head Hidden Gem
2 bedrooms, 2 beds
8–13 Sept
4.9 out of 5 average rating, 216 reviews