Hilton Head Island Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

5403 Treetops, Renovated 2 BR Villa, Free Bikes, Pool, Te...

Hilton Head Island
5403 Treetops, Renovated 2 BR Villa, Free Bikes, Pool, Tennis, Beach This newly renovated villa has...
Villa 2 / 2.5 / 6

*
Online booking available

$99 - $149
Per Night

$495 - $995
Per Week

105 Beachwalk-Fully-1st Floor & Renovated, Quick walk to ...

Hilton Head Island
105 Beachwalk-Fully-1st Floor & Renovated, Quick walk to Shipyard Beach Club Within earshot of the ...
Villa 2 / 2 / 6

*
Online booking available

$595 - $1395
Per Week

New To Market! Immaculate Shelter Cove Villa, Free Bikes,...

Hilton Head Island
New To Market! Immaculate Shelter Cove Villa, Free Bikes, Pool, Wifi 2 Bedrooms, 2 Bathrooms, Elev...
Villa 2 / 2 / 8

*
Online booking available

$113 - $164
Per Night

$495 - $1095
Per Week

Beautiful Spotless 148 Windward Villa, Golf Views, Free B...

Hilton Head Island
Beautiful Spotless 148 Windward Villa, Golf Views, Free Bikes, Pool, Hot Tub This charming villa is...
Villa 2 / 2.5 / 4

*
Online booking available

$113 - $164
Per Night

$495 - $1095
Per Week

Sand Dollar 31, 4 Bedrooms, Large Private Pool, Sleeps 12

Hilton Head Island
31 Sand Dollar Road in Folly Field is a Beach House with private pool only a 2-minute walk to the be...
Home 4 / 2 / 12

*
Online booking available

$319 - $784
Per Night

$1595 - $3921
Per Week

Fiddler's Cove 28C, 2 Bedroom, Sleeps 6, Pool

Hilton Head Island
Hilton Head Island's best-kept secret! You can experience an economic vacation near the beach, golf,...
Condo 2 / 2 / 6

*
Online booking available

$139 - $259
Per Night

$695 - $1295
Per Week

Village House 101, 2 Bedrooms, Pet Friendly, Pool, Sleeps 8

Hilton Head Island
101 Village House in Port Royal Plantation. This beautiful 2BR/2BA pet-friendly villa, located just ...
Condo 2 / 2 / 8

*
Online booking available

$114 - $241
Per Night

$750 - $1444
Per Week

St. Andrews Common 1751, 1 Bedroom, Ground Level, Large Pool

Hilton Head Island
St. Andrews Common 1751 in Palmetto Dunes. New to the program and ready to welcome you to your next ...
Condo 1 / 2 / 4

*
Online booking available

$119 - $230
Per Night

$595 - $1150
Per Week

New to Market! Pet Friendly Evian Villa. Free Bikes, Tenn...

Hilton Head Island
New to Market! Pet Friendly Evian Villa. Free Bikes, Tennis, Pool Sleeps 6 New Updates for 2017!...
Villa 2 / 2.5 / 6

*
Online booking available

$113 - $166
Per Night

$495 - $1095
Per Week

Shell Ring Road 63

Hilton Head Island
This is a Pet Friendly Home! (Dogs Only - Must Call for Details) This spacious ranch-style home off...
Home 3 / 3 / 8

*
Online booking available

$360 - $770
Per Night

$1820 - $3850
Per Week

1 Collier Beach Road: Oceanview, Singleton Beach, Pet Fri...

Hilton Head Island
First Floor: Living Area (Sleeper Sofa), TV, Full Bath, Access to the Pool (20’ x 9’), Gas Grill (Pr...
Home 5 / 6.5 / 16

*
Online booking available

$640 - $1200
Per Night

$3465 - $8400
Per Week

North Sea Pines Drive 82, 3 Bedroom, Golf View, Sleeps 7

Hilton Head Island
82 North Sea Pines Drive is a cozy 3 bedroom, 2 bath charming Sea Pines home with an excellent locat...
Home 3 / 2 / 7

*
Online booking available

$164 - $414
Per Night

$1150 - $2483
Per Week

Beautiful Views of Private Pool, Spa, Lagoon & Golf. Pet ...

Hilton Head Island
Beautiful Views of Private Pool, Spa, Lagoon & Golf. Pet Friendly Home! **Red Maple 20** This ch...
Home 4 / 4 / 12

*
Online booking available

$380 - $500
Per Night

$1900 - $3750
Per Week

Mooring Buoy 48

Hilton Head Island
This is a Pet Friendly Home! (Dogs Only - Must Call for Details) With only a two minute walk to the...
Home 4 / 6 / 14

*
Online booking available

$670 - $1455
Per Night

$3395 - $7315
Per Week

Heritage Road 02

Hilton Head Island
This is a Pet Friendly Home! (Dogs Only - Call for Details) Heritage Road 2 is located near Harbour...
Home 4 / 4 / 8

*
Online booking available

$370 - $1325
Per Night

$1855 - $6650
Per Week

1425 South Beach Villa

Hilton Head Island
Welcome to 1425 South Beach Villa located in Sea Pines Plantation across from South Beach Marina! Th...
Villa 4 / 3 / 10

*
Online booking available

$230 - $475
Per Night

$1610 - $3325
Per Week

4 Ocean Breeze Townhome, 3 Pools, Tennis, Beach, Pet Frie...

Hilton Head Island
4 Ocean Breeze Townhome, 3 Pools, Tennis, Beach, Pet Friendly Escape to the Beach! First Floor Mas...
Condo 3 / 3 / 8

*
Online booking available

$133 - $224
Per Night

$695 - $1495
Per Week

New Rental! 4th Row Ocean, 4 Bd, 2.5 Ba Pet Friendly, Pri...

Hilton Head Island
New Rental! 4th Row Ocean, 4 Bd, 2.5 Ba Pet Friendly, Private Pool! Nighthawk * 4th Row Ocean Home ...
Home 4 / 2.5 / 9

*
Online booking available

$299 - $599
Per Night

$1395 - $3995
Per Week

Mizzenmast Court 02

Hilton Head Island
This is a Pet Friendly Home! (Dogs Only - Must Call for Details & Fee) This three story home is loc...
Home 5 / 4 / 15

*
Online booking available

$420 - $3350
Per Night

$2135 - $16765
Per Week

Newly Furnished Beautiful Pet Friendly Vacation Home, 3 B...

Hilton Head Island
Newly Furnished Beautiful Pet Friendly Vacation Home, 3 Bds, 2 Ba 11 Deer Run Completely new furnis...
Home 3 / 2 / 8

*
Online booking available

$183 - $625
Per Night

$1095 - $2500
Per Week

St. Andrews Common 1774, 1 Bedroom, Pool, Pet Friendly, S...

Hilton Head Island
1774 St. Andrews in Palmetto Dunes. This totally redecorated beautiful 1BR/1.5 BA pet-friendly 1st-f...
Condo 1 / 1.5 / 4

*
Online booking available

$119 - $230
Per Night

$595 - $1150
Per Week

Renovated 2 Bed/2.5 Bath Pet Friendly Villa, Free Bikes, ...

Hilton Head Island
Renovated 2 Bed/2.5 Bath Pet Friendly Villa, Free Bikes, Tennis, Pool, Beach You will be convenient...
Villa 2 / 2.5 / 6

*
Online booking available

$99 - $149
Per Night

$495 - $995
Per Week

Ketch Court 825

Hilton Head Island
This is a Pet Friendly Villa! (Dogs Only - Must Call for Details) Ketch Court 825 is a two bedroom ...
Villa 2 / 1 / 6

*
Online booking available

$155 - $545
Per Night

$770 - $2730
Per Week

Carolina Place 3417, 3 Bedrooms, Sea Pines, Pool, Tennis,...

Hilton Head Island
If you are looking for a bright, airy floor plan and an end unit with a tranquil setting overlooking...
Condo 3 / 3 / 8

*
Online booking available

$190 - $390
Per Night

$950 - $1950
Per Week

8 Osprey - Oceanviews from your porch & 25 steps to the b...

Hilton Head Island
8 Osprey - Oceanviews from your porch & 25 steps to the beach. Just steps to the beach! This newly ...
Home 5 / 3.5 / 11

*
Online booking available

$3095 - $6295
Per Week

Hilton Head Island Getaway Information

Once you step onto Hilton Head Island you will immediately understand why it has been such a popular resort town for years. The many golf courses, restaurants, beaches, historical sights, and outdoor activities make a Hilton Head vacation home rental the perfect choice for your next family trip.

Located about an hour and a half south of Charleston, Hilton Head Island is one of the largest barrier islands along the Atlantic coast. The island is rich with history, having been home to ancient Native American inhabitants, explorers from Europe, grand plantations, civil war battles and more. Many sites exist today for visitors to learn about the fascinating history of the island. The island is particularly well known for its golf courses, most notably the Harbour Town Golf Links, which hosts the annual PGA Verizon Heritage Classic. The Harbour Town Lighthouse, which looms behind the 18th hole has come to represent the course and the island. Another symbol of the Harbour Town area is the age old Liberty Oak Tree. With the help of Hilton Head locals, this majestic tree has been carefully preserved and serves as a backdrop for many nights filled with entertainment and friends. Another popular part of the island is the South Beach area. South Beach is home to many specialty shops, restaurants, and a marina. The most famous of the restaurants is undoubtedly the Salty Dog Cafe. Most vacationers would find a trip to Hilton Head incomplete without a visit to this landmark. When it comes to outdoor activities, Hilton Head is in no short supply. The Sea Pines Forester Preserve is a stretching expanse of breathtaking plants and wildlife. You can explore the area on your own or take one of the many guided tours that are offered. The island is also home to freshwater forested wetlands, freshwater marshes, and saltwater marshes, all which enhance the natural beauty of the island. Many people visiting Hilton Head hope for a chance to see the Loggerhead Sea Turtles which make their nests on the ocean shore. The people of the island have gone to great lengths to protect these turtles and ask that all guests enjoy the creatures from a distance. All of the beaches on Hilton Head are open to the public, but a great deal of the beach access is private. To ensure that everyone can easily get to the beach, the town provides seven public beach access sites at various locations around the island. Some of the beaches have designated swimming areas and during the warmer months lifeguards are usually stationed at them and the other crowded beaches. When you feel like getting out onto the water there are many opportunities for sailing, parasailing, and day cruises. Other activities the whole family can partake in include making your way around the island and checking out the nine lighthouses or visiting the Coastal Discovery Museum, a children's museum featuring displays on marine life, outdoor butterfly gardens, and more.

More Getaway Locations and Properties