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

Top guest favourite
Apartment in Hilton Head Island
Ocean/Marsh View KING BED Beach Bar GYM Pickleball
1 bedroom, 2 beds, 1 private bathroom
18–23 Oct
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4.97 out of 5 average rating, 355 reviews
Top guest favourite
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, 24 reviews
Top guest favourite
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, 94 reviews
Guest favourite
Home in Hilton Head Island
Walk2Beach~Pool~Putting Green~Fenced Yard~EV
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Sea Pines
High Cotton in Sea Pines
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Apartment in Hilton Head Island
Beautiful Oceanfront Condo at Island Club
2 bedrooms, 3 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
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, 14 reviews
Home in Palmetto Dunes
2-story house with private heated outdoor pool, st
3 bedrooms, 6 beds, 3 bathrooms
6–13 Sept
Guest favourite
Apartment in Shelter Cove
Marriott Sunset Pointe - 2BD
2 bedrooms, 3 beds, 2 bathrooms
12–17 Dec
4.97 out of 5 average rating, 32 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
Guest favourite
Home in Palmetto Dunes
Luxury Palmetto Dunes Retreat with Private Pool
4 bedrooms, 6 beds, 5 bathrooms
14–19 Sept
4.91 out of 5 average rating, 23 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
Top guest favourite
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
Guest favourite
Home in Hilton Head Island
Spacious Deck, Hot Tub, Second Row To Beach & Bra
3 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Sea Pines
Family Memories Are Made Better at Deer Run
3 bedrooms, 4 beds, 3 bathrooms
7–12 Nov
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Palmetto Dunes
Spacious dog-friendly villa, walk to the beach
3 bedrooms, 6 beds, 2.5 bathrooms
6–11 Sept
4.9 out of 5 average rating, 102 reviews
Top guest favourite
Home in Sea Pines
Sea Pines Home w Large Deck | Great for Couples!
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
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
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