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Over 1,000 places in Hilton Head Island

Superhost
Vacation home in Hilton Head Island
3BD Condo w/ Indoor pool -Walk to Beach & CoCo's
5 beds
Oct 8 – 13
$351 per night
Home in Hilton Head Island
3 BR condo with amazing view
4 beds
Oct 1 – 6
$500 per night
Condo in Hilton Head Island
"Serenity Cove" Spectacular Villa on Broad Creek !
2 beds
Oct 20 – 25
$187 per night
Condo in Hilton Head Island
Comfortable & Affordable Villa In Central Location
3 beds
Oct 28 – Nov 2
$250 per night
Superhost
Condo in Hilton Head Island
Beach Hideaway 3BR 2BA In/Out Pools Full Kitchen
5 beds
Oct 1 – 6
$220 per night
Superhost
Condo in Hilton Head Island
Walk to Ocean-Palmetto Dunes Resort-Centre Court
4 queen beds
Oct 20 – 25
$219 per night, originally $289
Superhost
Condo in Hilton Head Island
Oceanview4U with Washer and Dryer! Great views!
5 beds
Oct 11 – 16
$270 per night
Superhost
Condo in Hilton Head Island
Cozy Beach Villa #3102, steps to indoor pool
4 beds
Oct 1 – 6
$145 per night
Home in Hilton Head Island
Walk to beach, new construction, pool coming soon!
5 beds
Oct 1 – 6
$373 per night
Superhost
Condo in Hilton Head Island
Relaxing and comfy condo with lots of amenities!
5 beds
Oct 14 – 19
$155 per night
Superhost
Condo in Hilton Head Island
Oceanview condo in Hilton Head with private beach
4 beds
Oct 1 – 6
$173 per night
Superhost
Condo in Hilton Head Island
Sunset Cove HHI- Water View Villa close to beach
4 beds
Oct 7 – 12
$299 per night
Superhost
Condo in Hilton Head Island
1400 sq ft. 2 Story Condo- Forest Beach
4 beds
Oct 31 – Nov 5
$104 per night
Superhost
Condo in Hilton Head Island
Clean Renovated Ground floor Encl Courtyard Bikes
2 beds
Oct 19 – 24
$155 per night
Superhost
Villa in Hilton Head Island
Beautiful Villa. 196 The Greens
4 beds
Oct 1 – 6
$394 per night
Superhost
Condo in Hilton Head Island
Spacious Two Bedroom Villa in Hilton Head Resort!
4 beds
Oct 7 – 12
$145 per night
Condo in Hilton Head Island
Fiddler's Cove Beach & Racquet BaronyGolf view
4 beds
Oct 29 – Nov 3
$121 per night
Superhost
Vacation home in Hilton Head Island
Walk to Harbour Town-Sea Pines Resort-Renovated
4 beds
May 23 – 28
$483 per night