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

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Guest favorite
Condo in Hilton Head Island
Luxe Hilton Head Beach Villa w/ Pool Views
5 guests2 bedrooms3 beds2 baths
May 16 – 21
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May 16 – 21
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ﺩ.ﺇ4,125 for 5 nights
for 5 nights

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Superhost
Home in Hilton Head Island
Newly Renovated Condo HiltonHead
Free cancellation
May 12 – 17
ﺩ.ﺇ4,594 for 5 nights
for 5 nights
New place to stay
Superhost
Apartment in Hilton Head Island
Comfortable Beach/Pool Waterfront Haven 2025 Redo
2 king beds
May 4 – 9
ﺩ.ﺇ3,213 for 5 nights
for 5 nights
New place to stay
Guest favorite
Home in Hilton Head Island
Hilton Head Island Beach House - Sea Pines Resort
Free cancellation
May 11 – 16
ﺩ.ﺇ11,774 for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Hilton Head Island
Changes in Latitude / WLK TO BEACH & Restaurants
Free cancellation
May 11 – 16
ﺩ.ﺇ4,899 for 5 nights
for 5 nights
4.98 out of 5 average rating, 59 reviews
Guest favorite
Condo in Hilton Head Island
Oceanfront Luxury! KING BED 65"TVs Pickleball BAR!
2 beds
May 18 – 23
ﺩ.ﺇ7,027 for 5 nights
for 5 nights
4.97 out of 5 average rating, 285 reviews
Apartment in Hilton Head Island
Seaside Villas Escape full condo 1 bedroom + bunks
3 beds
May 3 – 8
ﺩ.ﺇ3,194 for 5 nights
for 5 nights
Top guest favorite
Condo in Hilton Head Island
(5) Location! Walk to Coligny Beach Shops Dining!
3 beds
May 18 – 23
ﺩ.ﺇ3,672 for 5 nights
for 5 nights
4.95 out of 5 average rating, 512 reviews
Home in Hilton Head Island
Quiet condo steps from the beach
2 beds
May 2 – 7
ﺩ.ﺇ4,478 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Guesthouse in Bluffton
Beautiful Carriage House! Your Home Away from Home
2 beds
May 4 – 9
ﺩ.ﺇ2,049 for 5 nights
for 5 nights
4.93 out of 5 average rating, 247 reviews
Guest favorite
Apartment in Hilton Head Island
Beachfront Penthouse w/elevator
Free cancellation
May 9 – 14
ﺩ.ﺇ6,698 for 5 nights
for 5 nights
4.94 out of 5 average rating, 35 reviews
Top guest favorite
Condo in Hilton Head Island
MyStay at 1027 Caravel Ct.-Lighthouse View & Pool!
4 beds
May 10 – 15
ﺩ.ﺇ5,884 for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Hilton Head Island
5 Bedroom-Beach Access-Pool-Sleeps 14!
11 beds
May 2 – 7
ﺩ.ﺇ14,840 for 5 nights
for 5 nights
4.94 out of 5 average rating, 71 reviews
Superhost
Apartment in Hilton Head Island
My Blue Heaven #2 Hosted by Dorothy, New Listing
1 bed
May 4 – 9
ﺩ.ﺇ4,187 for 5 nights
for 5 nights
Top guest favorite
Condo in Hilton Head Island
Beach&Tennis, Stylish, Modern, Folly Field Beach!
Free cancellation
May 18 – 23
ﺩ.ﺇ3,360 for 5 nights
for 5 nights
4.96 out of 5 average rating, 141 reviews
Superhost
Home in Hilton Head Island
Modern Beach Escape | Private Pool~Steps to Beach
4 beds
May 4 – 9
ﺩ.ﺇ10,702 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Condo in Hilton Head Island
High Tide - Elevated Beachfront Oceanview Retreat
3 beds
May 18 – 23
ﺩ.ﺇ4,628 for 5 nights
for 5 nights
4.96 out of 5 average rating, 50 reviews
Superhost
Condo in Hilton Head Island
Marriott Sunset Pointe - 2BD
Free cancellation
Nov 16 – 21
ﺩ.ﺇ2,179 for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews
Home in Hilton Head Island
Charming Pet-Friendly Beach Home
Free cancellation
May 17 – 22
ﺩ.ﺇ4,283 for 5 nights
for 5 nights
New place to stay