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

Top guest favorite
Wake to unobstructed ocean views from your private balcony at this Hilton Head condo
1 bedroom, 2 beds, 1 private bath
Aug 16 – 21
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4.96 out of 5 average rating, 222 reviews
Top guest favorite
Wake to lighthouse and marina views from your balcony at this Harbour Town condo
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 4 beds, 2 baths
Sep 19 – 24
Top guest favorite
This remodeled beachfront condo in Hilton Head puts you steps from the ocean
4.99 out of 5 average rating, 447 reviews, 1 bedroom, 4 beds, 1 bath
Oct 27 – Nov 1
Top guest favorite
Wake to unobstructed ocean views from this top-floor Hilton Head Island condo
4.91 out of 5 average rating, 236 reviews, 1 bedroom, 3 beds, 1 bath
Oct 23 – 28
Top guest favorite
This mid-century treehouse puts you above the marsh near Harbour Town
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 20 – 25
Top guest favorite
Wake to ocean views from your balcony at this remodeled Hilton Head condo
4.97 out of 5 average rating, 314 reviews, 1 bedroom, 4 beds, 1 bath
Oct 9 – 14
Top guest favorite
Sit on your private balcony among centuries-old oaks at this Old Town Bluffton guesthouse
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 2 beds, 1 bath
Sep 7 – 12
Top guest favorite
This Sea Pines house gives you a new private pool, spa, and Golden Tee arcade
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 2 baths
Aug 16 – 21
Guest favorite
Wake to marsh views from this Hilton Head treehouse with bikes and a private deck
5.0 out of 5 average rating, 156 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 6 – 11
Top guest favorite
Watch the waves from your balcony at this beachfront Hilton Head condo
4.96 out of 5 average rating, 370 reviews, 1 bedroom, 4 beds, 1 bath
Sep 2 – 7
Live oaks and a private pool greet you at this Sea Pines home
New place to stay, 3 bedrooms, 6 beds, 2 baths
Aug 12 – 17
Guest favorite
This oceanfront Sea Pines house gives you a private beach path and patio under century oaks
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 3.5 baths
Sep 7 – 12
Top guest favorite
This Hilton Head Island house puts you a 4-minute walk from the beach, with a pool
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
Top guest favorite
This renovated Sea Pines penthouse puts you above Harbour Town in natural light
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 24 – 29
Top guest favorite
This Hilton Head Island house gives you a heated pool and elevator near the beach
5.0 out of 5 average rating, 122 reviews, 6 bedrooms, 15 beds, 4 baths
Oct 17 – 22
Top guest favorite
This Hilton Head condo puts you one block from Forest Beach with a shared pool
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 5 beds, 1.5 baths
Dec 20 – 25
Top guest favorite
Wake to sunrise over the ocean from your balcony at this Hilton Head condo
4.98 out of 5 average rating, 42 reviews, 1 bedroom, 2 beds, 1 bath
Aug 27 – Sep 1
Top guest favorite
Hear the waves from your screened porch at this Hilton Head Island townhouse
4.91 out of 5 average rating, 193 reviews, 2 bedrooms, 4 beds, 2.5 baths
Aug 25 – 30
Guest favorite
Lagoon views from your private deck at this Palmetto Dunes villa
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 2.5 baths
Aug 17 – 22