Home Vacation Rentals By Owner In Hilton Head Island, SC

Showing 2100 Of 7786 Vacation Rentals
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Exceptional(105)

$414.7

/ Nightly
Villa

Grace Meadows: 3BR/3BA, close To Westin, Beach, Golf & Tennis

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(27)

$368.23

/ Nightly
Condo

Pet Friendly Beach Villa 3 Bed 3 Bath walk to the beach, pools, tennis and more!16 OB

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(26)

$300.21

/ Nightly
Condo

Pet Friendly Beach Villa 2 Bed 2 Bath #7105 TreeTops

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$375.93

/ Nightly
Condo

Coastal Villa w/ Screened-in Porch & Walk to Beach

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(45)

$379.59

/ Nightly
Condo

Pet Friendly 3 Bed 3 Bath #3 Ocean Breeze Villa

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(24)

$378.86

/ Nightly
Condo

Beach Living - 3 Bed 2 Bath Seascape Villa - Just steps to the beach

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(36)

$377.39

/ Nightly
Condo

Beach close best of the best 3bd 3 ba pet friendly

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(71)

$298.01

/ Nightly
Condo

Beautiful 2 Bed2 Bath Shelter Cove Anchorage Villa

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(17)

$379.59

/ Nightly
Condo

Ocean Breeze 3 Bed 3 Ba Villa - Walk to the beach

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(34)

$1226.22

/ Nightly
Private Vacation Home

2nd Row 5 Bed 3 and one half Bath Pet Friendly Ocean View Beach House

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 3

Bath

Sleep 11

Sleeps
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$419.24

/ Nightly
Condo

Top Floor Shipyard Villa w/ Screened Balcony Overlooking Pool, Near Beach

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(7)

$1318.07

/ Nightly
Private Vacation Home

Sleeps 18 Near Driessen Beach, Elevator, 2 Great Rooms & Ocean View Patios

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 7

Bath

Sleep 18

Sleeps
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Exceptional(2)

$437.78

/ Nightly
Condo

Renovated Ground Level Shipyard Villa on the Golf Course, Trail to the Beach

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(11)

$1203.39

/ Nightly
Private Vacation Home

4th Row Sea Pines Home w/ Private Pool, Spa & Path to the Beach, Sleeps 12

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(19)

$388.3

/ Nightly
Villa

Charming Hilton Head Island Vacation Retreat with Shaded Private Patio!

Hilton Head, South Carolina, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(5)

$998.38

/ Nightly
Private Vacation Home

30 Dune Lane-The Seahorse

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 8

Bath

Sleep 18

Sleeps
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Exceptional(66)

$1155.73

/ Nightly
Private Vacation Home

New Custom Built 6br. Pet Friendly and Gated home Book your Late Summer Vacation

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 5

Bath

Sleep 18

Sleeps
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Exceptional(2)

$521.09

/ Nightly
Villa

Marriott Grande Ocean Resort, July 31-August 7, 2026. First-Class Luxury!

Hilton Head, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(103)

$637.27

/ Nightly
Condo

Oceanfront, Sweeping Water Views/Sunsets, Pool, Luxury Sea Pines Villa

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(6)

$611.94

/ Nightly
Private Vacation Home

Residential Beach Area Home w/ Private Pool

Hilton Head Island, South Carolina, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Hilton Head Island

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Exceptional(6)

$1391.79

/ Nightly
Private vacation home

3rd Row Ocean ~ Five Bedroom Sea Pines Home ~ Private Pool & Spa ~ Sleeps 20

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 16

Sleeps
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Exceptional(6)

$1371.94

/ Nightly
Private vacation home

4 Elderberry Ln, New Build, Elevator, Steps to Beach, Putting Green, Private Pool

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 7

Bath

Sleep 18

Sleeps
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Exceptional(6)

$1373.75

/ Nightly
Private vacation home

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

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(6)

$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

Bed 5

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(6)

$1385.82

/ Nightly
Private vacation home

Pvt Pool/Spa-Game Room-Theater-Cold Plunge-Sauna-2min Walk to Beach

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 4

Bath

Sleep 17

Sleeps
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Exceptional(6)

$1386.57

/ Nightly
Private vacation home

10 Wood Ibis: A NEW BESTNEST by Beverly Serral

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(6)

$1390.63

/ 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

Bed 6

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(6)

$1402.59

/ Nightly
Private vacation home

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

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 4

Bath

Sleep 18

Sleeps
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Exceptional(6)

$1422.67

/ Nightly
Private vacation home

1A Sea Lane - 4th Row Exceptional Family Home with Private Pool & Spa!

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 7

Bath

Sleep 20

Sleeps
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Exceptional(6)

$1418.40

/ Nightly
Private vacation home

17 Dune Ln-The Cottage-Oceanfront, Super Cute! Fire Pit, Pool & Spa

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 7

Bath

Sleep 16

Sleeps

Most Popular Cities in South Carolina