Home Vacation Rentals By Owner In Hilton Head Island, SC

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Condo

Pet Friendly Harbour Town Villa, Walk to Marina, Lighthouse & Waterfront Dining

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Hotel Resort

Spacious 2BR/2BA Golf Course Resort Condo Available September 27-October 3, 2026

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Hotel Resort

Marriott's Harbour Point - Hilton Head Island 2 Bedroom Villa

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(38)

$391.88

/ Nightly
Condo

Jim's Direct Oceanfront 3BR Penthouse HHI Villa

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(2)

$404.01

/ Nightly
Private Vacation Home

Sea Pines 3BR by Harbour Town - Pool, Fire Pit

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(32)

$651.5

/ Nightly
Villa

The Pool Is At Your Doorstep!

Hilton Head, South Carolina, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(9)

$400.85

/ Nightly
Condo

1407 South Beach Villa - Just steps away from the Beach!

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(4)

$169.4

/ Nightly
Apartment

Sandy Toes at The Sands | Walk to Coligny Beach

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(31)

$884.11

/ Nightly
Condo

Colossal Luxury Villa, w/ Pool & Spa Hilton Head

Hilton Head Island, South Carolina, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(43)

$213.95

/ Nightly
Condo

Beachfront Resort Villa steps from the beach w/2 pools, pickle ball, bike rental

Hilton Head Island, South Carolina, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(11)

$498.27

/ Nightly
Condo

Island Club 5301 | Oceanfront, Large Resort Pool!

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(10)

$324.22

/ Nightly
Villa

Sunset Rentals | Bluff Villas 1660

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(5)

$359.94

/ Nightly
Villa

Sunset Rentals | Continental Club 6

HIlton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$659.04

/ Nightly
Private Vacation Home

Sunset Rentals | Forest Drive 19 | Dog Friendly

Hilton Head Island, South Carolina, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(16)

$457.6

/ Nightly
Villa

Beautiful Beach Villa in Prestigious Palmetto Dunes, just steps to the beach!

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(11)

$316.33

/ Nightly
Villa

Sunset Rentals | Ocean Breeze 44 | Dog Friendly

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$242.19

/ Nightly
Condo

After Dune Delight Top Floor-Hilton Head Island, 2 Bed/2 Bath

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$588.64

/ Nightly
Villa

184 Twin Oaks at The Sea Pines Resort

Hilton Head Island, South Carolina, United States

Bed 3

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(41)

$316.37

/ Nightly
Condo

Island Club 5303 - Oceanfront Condo Newly remodeled for 2023

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$365.92

/ Nightly
Condo

Pet-Friendly Villa | 5 min. Walk to Folly Field Beach | First Floor

Hilton Head Island, South Carolina, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Home Most popular vacation rentals in Hilton Head Island

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Exceptional(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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

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