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

Guest favorite
Condo in Hilton Head Island
Steps to Lighthouse & Marina + 2BR + Pool Access
2 bedrooms, 3 beds, 2 private baths
Aug 30 – Sep 4
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4.95 out of 5 average rating, 104 reviews
Top guest favorite
Treehouse in Hilton Head Island
Luxury Waterfront Tree House | Harbour Town | Pool
3 bedrooms, 3 beds, 2 baths
Aug 20 – 25
5.0 out of 5 average rating, 36 reviews
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Condo in Hilton Head Island
Ocean Front Resort Condo
1 bedroom, 4 beds, 1 bath
Oct 27 – Nov 1
4.99 out of 5 average rating, 447 reviews
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Apartment in Hilton Head Island
Incredible Hilton Head condo - private beach!
2 bedrooms, 5 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 8 reviews
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Condo in Hilton Head Island
Breathtaking OCEAN VIEW |Pool & Coligny| TOP FLOOR
1 bedroom, 3 beds, 1 bath
Oct 23 – 28
4.91 out of 5 average rating, 236 reviews
Top guest favorite
Condo in Hilton Head Island
Ocean Views at Villamare 1405, Steps to the Beach!
2 bedrooms, 3 beds, 2 baths
Aug 24 – 29
4.96 out of 5 average rating, 84 reviews
Guest favorite
Home in Hilton Head Island
Walk to Harbour Town: Airy Treehouse w/ Bikes
2 bedrooms, 3 beds, 2 baths
Sep 6 – 11
5.0 out of 5 average rating, 156 reviews
Top guest favorite
Apartment in Hilton Head Island
Ocean Front Condo w/ Private Water Front Balcony
1 bedroom, 2 beds, 1 bath
Aug 27 – Sep 1
4.98 out of 5 average rating, 42 reviews
Top guest favorite
Apartment in Hilton Head Island
Penthouse flat in Sea Pines | Harbour Town
2 bedrooms, 2 beds, 2 baths
Oct 24 – 29
5.0 out of 5 average rating, 26 reviews
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Guesthouse in Bluffton
Cozy Carriage House Under Oaks | Old Town Bluffton
1 bedroom, 2 beds, 1 bath
Sep 7 – 12
5.0 out of 5 average rating, 12 reviews
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Townhouse in Hilton Head Island
Ocean Gate 13 Walk to beach villa with pickleball
2 bedrooms, 4 beds, 2.5 baths
Aug 25 – 30
4.91 out of 5 average rating, 193 reviews
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Condo in Hilton Head Island
Updated Coastal Condo- Biking -3 min Walk to Shore
2 bedrooms, 5 beds, 1.5 baths
Dec 20 – 25
5.0 out of 5 average rating, 7 reviews
Top guest favorite
Home in Hilton Head Island
Location Matters! Walk to Beach & Everything Else!
2 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
5.0 out of 5 average rating, 19 reviews
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Apartment in Hilton Head Island
Sea Pines Villa – Walk to Beach, Pool, & Salty Dog
3 bedrooms, 4 beds, 2 baths
Sep 25 – 30
4.95 out of 5 average rating, 44 reviews
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Home in Hilton Head Island
98 Sandcastle Ct
6 bedrooms, 15 beds, 4 baths
Oct 17 – 22
5.0 out of 5 average rating, 122 reviews
Top guest favorite
Condo in Hilton Head Island
MyStay at 1027 Caravel Ct.-Lighthouse View & Pool!
2 bedrooms, 4 beds, 2 baths
Sep 19 – 24
4.97 out of 5 average rating, 35 reviews
Top guest favorite
Villa in Hilton Head Island
Oceanfront Scandi Oasis Amazing View & Heated Pool
1 bedroom, 3 beds, 1 bath
Aug 18 – 23
4.97 out of 5 average rating, 132 reviews
Home in Hilton Head Island
Sea Pines Haven | Private Pool | Harbour Town
3 bedrooms, 6 beds, 2 baths
Aug 13 – 18
New place to stay
Top guest favorite
Apartment in Hilton Head Island
Harbour Town Marina Studio | Walk to Lighthouse
1 bedroom, 1 bed, 1 bath
Aug 17 – 22
5.0 out of 5 average rating, 28 reviews