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

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Top guest favourite
Apartment in Hilton Head Island
Oceanfront Luxe KING BED 65TV Beach Bar Pickleball
1 bedroom, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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4.98 out of 5 average rating, 365 reviews
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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, 23 reviews
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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
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Apartment in Palmetto Dunes
Ocean Views at Villamare 1405, Right on the Beach!
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 85 reviews
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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, 68 reviews
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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
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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
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Flat in Hilton Head Island
Luxury 2026 Renovation+Oceanfront Views!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Shipyard
French Home on Golf Course Private Pool & Hot Tub
4 bedrooms, 5 beds, 2.5 bathrooms
30 Oct – 4 Nov
4.8 out of 5 average rating, 5 reviews
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Apartment in Palmetto Dunes
MyStay at 789 Queen's Grant -Pets Ok + Pool, Beach
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 10 reviews
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Home in Sea Pines
Two Fawns at Sea Pines|4+BR|New Pool/Spa!
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 13 reviews
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Treehouse in Sea Pines
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 38 reviews
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Apartment in Palmetto Dunes
Ocean View | Top Floor | Walk to Beach | Pools!
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 291 reviews
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Apartment in Hilton Head Island
Shorewood 332
2 bedrooms, 3 beds, 2 bathrooms
22–27 Oct
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Townhouse in Hilton Head Island
Piece of Paradise on Hilton Head Island
2 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
4.92 out of 5 average rating, 168 reviews
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Home in Sea Pines
Sea Pines house ~ Golf Sim / Putting Green / Games
4 bedrooms, 4 bathrooms
16–21 Sept
5.0 out of 5 average rating, 93 reviews
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Apartment in Hilton Head Island
Beach condo in gated resort w/ tons of amenities!
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.91 out of 5 average rating, 195 reviews
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Apartment in Hilton Head Island
Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR
1 bedroom, 3 beds, 1 bathroom
1–6 Nov
4.91 out of 5 average rating, 237 reviews
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Flat in Sea Pines
Harbour Town Marina Studio | Walk to Lighthouse
1 bedroom, 1 king bed, 1 bathroom
30 Sept – 5 Oct
5.0 out of 5 average rating, 31 reviews