Hilton Head Island Vacation Rentals

Find the best deals on 7,761 vacation rentals in Hilton Head Island

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Top rentals in Hilton Head Island

Find the perfect Hilton Head Island vacation rental for your needs
Oceanfront Penthouse W/ Unmatched Views & Shared Pool, Hot Tub & Tennis!
Oceanfront Penthouse W/ Unmatched Views & Shared Pool, Hot Tub & Tennis!
8.8
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Sea Pines Marina with Ocean View
Sea Pines Marina with Ocean View
$102
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The Private Islands of Old House Cay
The Private Islands of Old House Cay
10.0
$763
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Completely Renovated In 2020! Oceanfront, Pool, Brand New Everything!
Completely Renovated In 2020! Oceanfront, Pool, Brand New Everything!
9.4
$531
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Quiet, Cozy Treehouse Near The Beach
Quiet, Cozy Treehouse Near The Beach
9.7
$178
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2230 Heritage Villas
2230 Heritage Villas
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13 St Andrews Place
13 St Andrews Place
$523
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25 Heath Drive ~ Private 4Br Home, Short Walk to Beach in Palmetto Dunes
25 Heath Drive ~ Private 4Br Home, Short Walk to Beach in Palmetto Dunes
$321
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Seapines 23 Lighthouse
Seapines 23 Lighthouse
$202
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Beautifully remodeled 1 bedroom villa located just a short walk to the beach
Beautifully remodeled 1 bedroom villa located just a short walk to the beach
9.8
$195
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Short Walk to Beach, on Fazio Golf Course, Private Pool/Spa
Short Walk to Beach, on Fazio Golf Course, Private Pool/Spa
$364
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Seapines 476 Plantation club villas
Seapines 476 Plantation club villas
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The Spa 1115 - Two Bedroom Condo
The Spa 1115 - Two Bedroom Condo
8.6
$257
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St Andrews Common 1753 - Two Bedroom Condo
St Andrews Common 1753 - Two Bedroom Condo
7.8
$69
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6 Sailmaster Commons - 2 Bedroom Shipyard Condo
6 Sailmaster Commons - 2 Bedroom Shipyard Condo
$235
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Intimate low country Carriage House with gorgeous appointments!
Intimate low country Carriage House with gorgeous appointments!
8.8
$135
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Evian 138 - Two Bedroom Condo
Evian 138 - Two Bedroom Condo
7.0
$44
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Family-Size Hilton Head Home in Sea Pines by Beach
Family-Size Hilton Head Home in Sea Pines by Beach
9.3
$360
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Island Club 2102, 2 Bedroom, Sleeps 7, Oceanfront, Large Pool, 1st Floor
Island Club 2102, 2 Bedroom, Sleeps 7, Oceanfront, Large Pool, 1st Floor
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Oceanview resort condo with pools, hot tubs, beach access, and much more!
Oceanview resort condo with pools, hot tubs, beach access, and much more!
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Bluff Villas 1733
Bluff Villas 1733
7.9
$161
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Free Golf Cart! Cozy 4bdr Home Waiting For You
Free Golf Cart! Cozy 4bdr Home Waiting For You
8.0
$621
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Sand Dollar Paradise
Sand Dollar Paradise
9.4
$85
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Fiddlers Cove
Fiddlers Cove
8.5
$165
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Fabulous 6BR/6BA Newly Renovated Beach House- Just 3 Houses from the Beach!
Fabulous 6BR/6BA Newly Renovated Beach House- Just 3 Houses from the Beach!
$1,173
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Queens Grant 675 3 Bedroom Villa
Queens Grant 675 3 Bedroom Villa
$158
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Cutter Court
Cutter Court
8.5
$174
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3bed/3bath, Daily Golf/Tennis included, 6/18-6/25/22 only
3bed/3bath, Daily Golf/Tennis included, 6/18-6/25/22 only
10.0
$197
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Hilton Head Cabanas #whh043
Hilton Head Cabanas #whh043
$161
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Ocean Dunes Villas Wod102
Ocean Dunes Villas Wod102
$195
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Picturesque PD villa -immaculate & spacious
Picturesque PD villa -immaculate & spacious
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The Evan Cottage - Recently Updated!
The Evan Cottage - Recently Updated!
9.5
$174
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Perfect Beach Getaway 2 Bedrooms 1.5 Bath
Perfect Beach Getaway 2 Bedrooms 1.5 Bath
$139
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Private Island - Soulfully Peaceful Access To Nature & Wildlife Watching
Private Island - Soulfully Peaceful Access To Nature & Wildlife Watching
10.0
$423
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4 Ginger Beer - Beautiful Multi Level Home, Short Walk to Palmetto Dunes Beach!
4 Ginger Beer - Beautiful Multi Level Home, Short Walk to Palmetto Dunes Beach!
10.0
$628
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Palmetto Dunes Resort Villa
Palmetto Dunes Resort Villa
$255
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Oceanview (Oceanfront Shorewood) Penthouse 5th Floor End Unit-Great Remodel
Oceanview (Oceanfront Shorewood) Penthouse 5th Floor End Unit-Great Remodel
9.9
$240
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Perfect Hilton Head Getaway with Private Pool. Sleeps 9. 3 Min To Beach
Perfect Hilton Head Getaway with Private Pool. Sleeps 9. 3 Min To Beach
$448
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Home Away Home 2
Home Away Home 2
7.7
$62
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3 Troon ~ Short 5 Minute Walk to the Beautiful Beaches in Palmetto Dunes
3 Troon ~ Short 5 Minute Walk to the Beautiful Beaches in Palmetto Dunes
$497
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3521 Villamare ~ Top Floor 2Br Villa with Ocean and Beach Views!
3521 Villamare ~ Top Floor 2Br Villa with Ocean and Beach Views!
$383
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Hhi 2br, 2ba Deluxe W/ Indoor Pool
Hhi 2br, 2ba Deluxe W/ Indoor Pool
$127
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Hilton Head Villa - Pools/Hot tub - Steps to the Beach
Hilton Head Villa - Pools/Hot tub - Steps to the Beach
9.5
$138
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Near Ocean Villas - Hilton Head's Best And Most Affordable Deluxe Villas Close To Beach
Near Ocean Villas - Hilton Head's Best And Most Affordable Deluxe Villas Close To Beach
10.0
$229
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Nestled In Sea Pines Our Home Is Right On The Golf Course
Nestled In Sea Pines Our Home Is Right On The Golf Course
$232
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When to book a vacation apartment in Hilton Head Island

Check out the tips below to find the best deal on a Hilton Head Island vacation rental property
Low Season
January
High Season
April

cheapest month to stay

44%

expected price decrease

most expensive time to stay

28%

expected price increase

Price
$166 - $403
Highest day of week
Sunday
Cheapest day of week
Friday

av. price over the last two weeks

Average price (weeknight)

$382

av. price over the last two weeks

av. price over the last two weeks

Average price (weekend night)

$456

av. price over the last two weeks


Cheapest vacation rentals in Hilton Head Island

Our lowest priced vacation apartments and property rentals for a cheaper way to stay in Hilton Head Island
The Spa 1115 - Two Bedroom Condo
The Spa 1115 - Two Bedroom Condo
8.6
$257

Hilton Head Island vacation apartments & rental properties FAQ

How long do people typically book vacation apartments for in Hilton Head Island?

3 nights is the typical length of a Hilton Head Island vacation rental booking.

How much does a vacation rental apartment in Hilton Head Island cost?

Renting a vacation apartment in Hilton Head Island will see a range in pricing typically determined by the season, location of the apartment and the number of rooms required. Recently, a typical search for apartment rentals in Hilton Head Island suggests an average of $208 per night.

When is the best time to book a vacation rental in Hilton Head Island?

January is typically when Hilton Head Island vacation apartment and rental property prices are at their lowest, with prices around 44% lower than the Hilton Head Island peak season.