Vacation Home Rentals By Owner In Hilton Head Island, SC

Showing 640 Of 2125 Vacation Rentals

Exceptional(7)

$1309.03

/ Nightly

Private Vacation Home

New fully renovated home 1 minute walk to the beautiful private beach access

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(1)

$1312.01

/ Nightly

Private Vacation Home

Luxury Retreat HHI w/ Private Pool + Walk to Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(28)

$1314.18

/ Nightly

Private Vacation Home

19 Pelican - Less than 3 minute walk to beach on beautiful HHI!

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(3)

$1320.12

/ Nightly

Private Vacation Home

Pet Friendly 6BR w/ Pool Slide, Fire Pit & Fenced Yard, Walk to Fish Haul Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(40)

$1327.32

/ Nightly

Private Vacation Home

16 Brigantine - Direct Oceanfront Home with Private Pool. Just Beautiful

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(44)

$1333.59

/ Nightly

Private Vacation Home

Stunning oceanfront home offering private pool & hot tub, steps from Coligny!

Hilton Head, South Carolina, United States

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Bath

Sleeps

Exceptional(60)

$1340.29

/ Nightly

Private Vacation Home

Jaw-Dropping Hilton Head Vacation House w/ Private Pool, Ocean Views!

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(19)

$1341.73

/ Nightly

Private Vacation Home

Oceanfront Estate - Pool, Hot Tub, Pool Table, Bonus Boat- Exclusive Location

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(46)

$1342.37

/ Nightly

Private Vacation Home

21 Holloman Trace-NEW BUILD, 5th Row, in Forest Beach with Pool at living level

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(20)

$1342.83

/ Nightly

Private Vacation Home

7BR Custom Home | Private Pool & Spa | Elevator | 5-Min to Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(8)

$1343.47

/ Nightly

Private Vacation Home

Luxury Beach Getaway/outdoor oasis-5 min. to beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(100)

$1352.69

/ Nightly

Private Vacation Home

OCEANFRONT W/POOL - FALL 2026 DATES AVAILABLE - BOOK NOW!! HHI PERMIT # 071512

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(1)

$1360.41

/ Nightly

Private Vacation Home

Luxury 5Br Home w/ Private Pool & Outdoor Dining

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(2)

$1360.78

/ Nightly

Private Vacation Home

Group Retreat w/ Shuffleboard, Air Hockey & Foosball, Near South Beach Marina

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

Exceptional(1)

$1376.77

/ Nightly

Private Vacation Home

58 Heritage Road - Harbour Town Golf Course Views & a Short Walk to the Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

$1378.03

/ Nightly

Private Vacation Home

Beachfront beauty with pool access fireplaces, jetted tub, balconies, & WD

Hilton Head, South Carolina, United States

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Bath

Sleeps

Exceptional(2)

$1386.57

/ Nightly

Private Vacation Home

10 Wood Ibis: A NEW BESTNEST by Beverly Serral

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(29)

$1390.61

/ Nightly

Private Vacation Home

7BR Ocean Views Oasis w/ Pool, Decks & Direct Singleton Access

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(158)

$1395.43

/ Nightly

Private Vacation Home

Castle by the Sea 7BR/8BA Luxury Home with Elevator

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1400.1

/ Nightly

Private Vacation Home

South Beach Serenity by AvantStay | Private Pool + Beachfront

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

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Most popular vacation rentals in Hilton Head Island

Exceptional(11)

$1418.28

/ Nightly

Private vacation home

Pet Friendly 6BR w/ Golf Simulator, Tiki Hut Bar, Private Pool & Spa

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1381.97

/ Nightly

Private vacation home

1 Loblolly Rd in Sea Pines - 5-Bedroom Home, Private Heated Pool/Spa, Sleeps 14.

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1386.57

/ Nightly

Private vacation home

10 Wood Ibis: A NEW BESTNEST by Beverly Serral

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

Exceptional(11)

$1390.86

/ Nightly

Private vacation home

Bayberry Family Beach House 5 BR 4 BA Pool Walk to Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1395.43

/ Nightly

Private vacation home

Castle by the Sea 7BR/8BA Luxury Home with Elevator

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1397.24

/ Nightly

Private vacation home

Stunning Lagoon Front Home with Private Pool and Spa, 4th row from the beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1412.11

/ Nightly

Private vacation home

79 Mooring Buoy- Beautiful home & Only a 3 Minute(180 yard)Walk to the Beach!

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1428.17

/ Nightly

Private vacation home

Newer home - steps from Burkes Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1451.51

/ Nightly

Private vacation home

Forest Beach Luxury Estate | Pool, Spa, Game Room & Steps to Beach

Hilton Head Island, South Carolina, United States

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Bath

Sleeps

Exceptional(11)

$1447.11

/ Nightly

Private vacation home

6 Bedroom, Free Heated Pool + Elevator Sleeps 26

Hilton Head Island, South Carolina, United States

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Bath

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Vacation Home Rentals By Owner In Hilton Head Island, SC

$1309.03

$1312.01

$1314.18

$1320.12

$1327.32

$1333.59

$1340.29

$1341.73

$1342.37

$1342.83

$1343.47

$1352.69

$1360.41

$1360.78

$1376.77

$1378.03

$1386.57

$1390.61

$1395.43

$1400.1

Rent a place that suits your needs

Most popular vacation rentals in Hilton Head Island

$1418.28

$1381.97

$1386.57

$1390.86

$1395.43

$1397.24

$1412.11

$1428.17

$1451.51

$1447.11

Most Popular Cities in South Carolina