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

Apartment in Shipyard
2BR Brigantine Quarters Condo – Dragonfly Layne
2 bedrooms, 4 beds, 2 shared bathrooms
8–15 Aug
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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, 119 reviews
Home in Hilton Head Island
Charming remodeled 4th row House walk to Beach !
4 bedrooms, 5 beds, 3 bathrooms
8–13 Jul
New place to stay
Home in Sea Pines
Two Fawns at Sea Pines|4+BR|New Pool/Spa!
4 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Sea Pines
Pet-Friendly, South Beach Pool Access, 3BR
3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
New place to stay
Luxe
Home in Sea Pines
29 South Beach, Sea Pines: Pool, Walk to Beach
4 bedrooms, 4 beds, 4.5 bathrooms
11–16 Jul
Top guest favourite
Home in Sea Pines
Hilton Ivory by AvantStay | Luxe Home + Pool/Patio
6 bedrooms, 10 beds, 4.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 6 reviews
Flat in Shipyard
Spacious 3 bedroom Beach Pool Tennis Pickleball !
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Flat in Hilton Head Island
SeaCrest 2512 Stunning, Walk to Coligny Shops/Rest
4 bedrooms, 7 beds, 3 bathrooms
2–7 Dec
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Hilton Head Island
Beach House, Elevator, Sleeps 12
3 bedrooms, 6 beds, 2.5 bathrooms
2–7 Aug
4.99 out of 5 average rating, 81 reviews
Guest favourite
Flat in Sea Pines
Seapines-2025 Remodel, Walk to Beach, End Unit
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Sea Pines
Coastal Chic Retreat Near Beach and Sea Pines.
1 bedroom, 1 king bed, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 33 reviews
Home in Shipyard
Greenside Haven | Gated, Beach, Golf, Pet-Friendly
3 bedrooms, 8 beds, 3.5 bathrooms
13–18 Jul
New place to stay
Home in Shipyard
Dog friendly home w/ an enclosed yard, pool deck,
4 bedrooms, 8 beds, 2 bathrooms
10–15 Oct
Apartment in Hilton Head Island
Beach, Pools, Hot Tub, Tennis walk Coligny Plaza !
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
New place to stay
Luxe
Villa in Sea Pines
1465 Sound Villas, Sea Pines: Beachfront Luxury
4 bedrooms, 5 beds, 5 bathrooms
8–13 Aug
Home in Sea Pines
Spacious, Renovated House with Private Spa and Pri
3 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
Top guest favourite
Treehouse in Sea Pines
Harbour Town Tree House | Private Office | HT Pool
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 94 reviews