Home Vacation Home Rentals By Owner In Hilton Head Island, SC

Showing 1480 Of 2131 Vacation Rentals
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Exceptional(41)

$1244.09

/ Nightly
Private Vacation Home

Luxury 2nd Row Home, Chefs Kitchen, Pool, Free Golf, Great for Entertaining

Hilton Head, South Carolina, United States

Bed 5

Bed

Bath 4

Bath

Sleep 16

Sleeps
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Exceptional(11)

$1244.51

/ Nightly
Private Vacation Home

18 Ibis Street- Book now, amazing ocean views.

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 8

Bath

Sleep 20

Sleeps
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Exceptional(17)

$1246.17

/ Nightly
Private Vacation Home

2 Sea Spray - Steps to the Beach... & Summer Weeks Waiting For You!

Hilton Head Island, South Carolina, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$1248.13

/ Nightly
Private Vacation Home

New Direct Oceanfront Available Starting Fall 2026 Best Views on HHI

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 7

Bath

Sleep 14

Sleeps
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Exceptional(12)

$1248.23

/ Nightly
Private Vacation Home

Golf course and lagoon views!

Hilton Head, South Carolina, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(39)

$1248.5

/ Nightly
Private Vacation Home

Island Cottage 3rd Row 5 Bedroom N Forest Beach Home steps to beach and Coligny

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(6)

$1251.17

/ Nightly
Private Vacation Home

South Forest Beach 5BR w/ Golden Tee, Ping Pong & 130 Inch Theater Screen

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 6

Bath

Sleep 15

Sleeps
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Exceptional(17)

$1251.95

/ Nightly
Private Vacation Home

SeaSide 48- Steps to Beach- 3rd Row, Private Pool, North Forest Beach, Sleeps 14

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(47)

$1252.12

/ Nightly
Private Vacation Home

Premium DOG FRIENDLY 4th Row Ocean Sea Pines Home with a Private Pool & Spa

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(9)

$1252.5

/ Nightly
Private Vacation Home

Large Sprawling Home Very Close to the Beach and Activities!

Hilton Head, South Carolina, United States

Bed 6

Bed

Bath 7

Bath

Sleep 12

Sleeps
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Exceptional(49)

$1253.29

/ Nightly
Private Vacation Home

29 South Beach Lane: A BESTNEST by Beverly Serral 4th Row Ocean, Private Pool

Hilton Head Island, South Carolina, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(123)

$1256.98

/ Nightly
Private Vacation Home

8 Wanderer - Oceanfront Home off North Forest w/ pool & hot tub. Dog Friendly!

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(3)

$1259.76

/ Nightly
Private Vacation Home

Modern Serenity - Steps to Beach and Coligny Plaza

Hilton Head Island, South Carolina, United States

Bed 4

Bed

Bath 3

Bath

Sleep 16

Sleeps
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Exceptional(162)

$1260.23

/ Nightly
Private Vacation Home

Luxury Oasis - Sunset Marsh Views Private Pool & 6 min walk to beach

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(119)

$1261.67

/ Nightly
Private Vacation Home

Oceanfront, Pool, Elevator, Free Golf, Views

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 6

Bath

Sleep 22

Sleeps
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Exceptional(1)

$1261.96

/ Nightly
Private Vacation Home

Luxury Sea Pines Vacation Home | Pool | Golf Course Views

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 6

Bath

Sleep 16

Sleeps
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Exceptional(46)

$1263.58

/ Nightly
Private Vacation Home

Pet friendly, 2nd row beach home with private pool and gorgeous new updates

Hilton Head Island, South Carolina, United States

Bed 4

Bed

Bath 4

Bath

Sleep 13

Sleeps
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Exceptional(34)

$1264.18

/ Nightly
Private Vacation Home

7 Bayberry - 2nd Row, 6BR/6.5BA, Fully Renovated, Steps from the Beach, Pool

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 6

Bath

Sleep 19

Sleeps
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Exceptional(25)

$1265.49

/ Nightly
Private Vacation Home

Private Pool, Close to Beach, Free Golf, Elevator

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 6

Bath

Sleep 18

Sleeps
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Exceptional(82)

$1266.65

/ Nightly
Private Vacation Home

Custom Putting Green, Game Room, Steps to Beach, Private Pool w/ TV, Elevator

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 6

Bath

Sleep 21

Sleeps
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Home Most popular vacation rentals in Hilton Head Island

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Exceptional(82)

$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

Bed 6

Bed

Bath 4

Bath

Sleep 14

Sleeps
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Exceptional(82)

$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(82)

$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(82)

$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

Bed 5

Bed

Bath 4

Bath

Sleep 18

Sleeps
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Exceptional(82)

$1395.43

/ Nightly
Private vacation home

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

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 8

Bath

Sleep 18

Sleeps
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Exceptional(82)

$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

Bed 5

Bed

Bath 6

Bath

Sleep 14

Sleeps
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Exceptional(82)

$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

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(82)

$1428.17

/ Nightly
Private vacation home

Newer home - steps from Burkes Beach

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 6

Bath

Sleep 24

Sleeps
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Exceptional(82)

$1451.51

/ Nightly
Private vacation home

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

Hilton Head Island, South Carolina, United States

Bed 7

Bed

Bath 5

Bath

Sleep 22

Sleeps
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Exceptional(82)

$1447.11

/ Nightly
Private vacation home

6 Bedroom, Free Heated Pool + Elevator Sleeps 26

Hilton Head Island, South Carolina, United States

Bed 6

Bed

Bath 4

Bath

Sleep 22

Sleeps

Most Popular Cities in South Carolina