Hilton Head Island Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

Tennismaster 203

Hilton Head Island
2 BD/2.5 BA townhouse overlooking pool. King, 2 Twin beds plus Sleep Sofa (linens for SS provided fo...
Villa 2 / 3 / 6

*
Online booking available

$160 - $240
Per Night

$800 - $1200
Per Week

Collier Beach 16

Hilton Head Island
5BD/5.5BA Oceanfront Home with Private Pool (can be heated for a fee)4 King beds, 1 Queen plus Sleep...
Home 5 / 6 / 12

*
Online booking available

$1000 - $2200
Per Night

$5000 - $11000
Per Week

Crabline Court 34

Hilton Head Island
5 BD/ 4 BA multi-story Home with Private Pool* & Spa* can be heated for *additional fee. King, King...
Home 5 / 4 / 12

*
Online booking available

$385 - $770
Per Night

$1925 - $3850
Per Week

105 Beachwalk - Fully Renovated and 5 minutes walk to the...

Hilton Head Island
105 Beachwalk - Fully Renovated and 5 minutes walk to the beach. Within earshot of the rolling surf...
Villa 2 / 2 / 6

*
Online booking available

$85 - $171
Per Night

$595 - $1395
Per Week

Beach Villa 13 - Oceanside Townhouse - Recently Updated

Hilton Head Island
Stay ocean-side and enjoy many benefits of an oceanfront complex. Guests staying in Beach Villa 13 e...
Condo 3 / 4 / 8

*
Online booking available

$235 - $395
Per Night

$1175 - $1975
Per Week

Shorewood 310

Hilton Head Island
2BD/2BA ocean front villa located on the 3rd floor. King bed, Queen &Twin bed. Sleep Sofa (linens pr...
Villa 2 / 2 / 7

*
Online booking available

$240 - $460
Per Night

$1200 - $2300
Per Week

Shorewood 539

Hilton Head Island
2 BD/ 2 BA 5th floor ocean view villa. King, Queen plus Sleep Sofa.(linens not provided for the slee...
Villa 2 / 2 / 6

*
Online booking available

$200 - $350
Per Night

$1000 - $1750
Per Week

Spinnaker Hilton Head 2 Bdr Condo with Golf / Tennis Package

Hilton Head Island
Weeks 39 and 40. Sat to Sat rental, spacious 2 floor condo, full kitchen, laundry, Jacuzzi tub, Wi-...
Condo 2 / 2.5 / 6

$1500 - $1500
Per Week

62 Night Heron-Cute Beach Cottage, 3 BRs & Quick 5 min wa...

Hilton Head Island
62 Night Heron-Cute Beach Cottage, 3 BRs & Quick 5 min walk to the ocean These cozy, 3 bedroom, 2 b...
Villa 3 / 2 / 6

*
Online booking available

$85 - $85
Per Night

$595 - $1595
Per Week

Feb 22 - Apr 26   **********20% ADVANCE BOOKING DISCOUNT... ************

4br -Direct Oceanfront Home..Private Pool and Spa

Hilton Head Island
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Home 4 / 3 / 12

$1500 - $5800
Per Week

Beach Villa 9 - Oceanside Townhouse-Gated Community

Hilton Head Island
Stay ocean-side and enjoy many benefits of an oceanfront complex without paying oceanfront prices. B...
Condo 3 / 3 / 7

*
Online booking available

$235 - $395
Per Night

$1175 - $1975
Per Week

Wow, this completely renovated 1 BR, 1 bath compact cottage

Hilton Head Island
QUIET INTIMACY OVERLOOKING A LUSH LAGOON. Wow, this updated 1 bedroom, 1 bath compact cottage is lo...
Home 1 / 1 / 3

*
Online booking available

$71 - $121
Per Night

$495 - $995
Per Week

57 Dune Lane

Hilton Head Island
Dune's Perch - in a league of its own. 7 bedrooms, 7.5 baths with *PRIVATE HEATED POOL AND SPA and p...
Home 7 / 8 / 16

*
Online booking available

$814 - $814
Per Night

$5695 - $14450
Per Week

Surf Court 12 - Forest Beach Townhouse

Hilton Head Island
Surf Court is an ocean-oriented complex with first-floor apartments, two-story and three-story townh...
Condo 2 / 2.5 / 6

*
Online booking available

$140 - $199
Per Night

$695 - $995
Per Week

25 Ruddy Turnstone - 5 Bedrooms & Beautiful.

Hilton Head Island
Gorgeous custom built Sea Pines home is ready for your family! 5 bedrooms with a den and a nursery a...
Home 5 / 6 / 12

*
Online booking available

$427 - $427
Per Night

$2995 - $7495
Per Week

1402 Seacrest - Fully renovated, 4th Floor Villa - Sleeps 8

Hilton Head Island
Completely Renovated - Just Beautiful!!! Incredible OCEANVIEWS from this 4th floor villa in Buildi...
Villa 2 / 2 / 8

*
Online booking available

$171 - $171
Per Night

$1200 - $2595
Per Week

223 Evian - 2nd Floor Flat w/ golf course views, pool & t...

Hilton Head Island
223 Evian - 2nd Floor Flat w/ golf course views, pool & tennis. This lovely 2nd floor townhouse is ...
Villa 2 / 2 / 6

*
Online booking available

$85 - $171
Per Night

$595 - $1395
Per Week

Shorewood 507

Hilton Head Island
3 BD/3 BA oceanfront villa. King, 2 Twin beds and 2 Twin beds. Large Oceanfront Pool, Hot Tub & B...
Villa 3 / 3 / 6

*
Online booking available

$265 - $530
Per Night

$1325 - $2650
Per Week

2 br/2 ba spinnaker shipyard townhouse

Hilton Head Island
2 br/2 ba spinnaker shipyard townhouse Unit Description: Located along picturesque fairways and Low...
Condo 2 / 2 / 6

*
Online booking available

$169 - $999
Per Night

$1183 - $6993
Per Week

Ocean One 409 - Oceanfront 4th Floor Condo

Hilton Head Island
With decks off the living room and master bedroom, guests staying in Ocean One 409 enjoy panoramic v...
Condo 2 / 2 / 7

*
Online booking available

$235 - $419
Per Night

$1175 - $2095
Per Week

2 bedroom townhome at hickory cove

Hilton Head Island
2 bedroom townhome at hickory cove Unit Description: Our Hickory Cove villas are located near the D...
Condo 2 / 3 / 6

*
Online booking available

$174 - $999
Per Night

$1218 - $6993
Per Week

31 Dune Lane Fantastic brand new 2014 custom built Oceanf...

Hilton Head Island
31 Dune Lane Fantastic brand new 2014 custom built Oceanfront- Avail 5/24 wk. Fantastic brand new c...
Home 6 / 7 / 19

*
Online booking available

$771 - $771
Per Night

$5395 - $13695
Per Week

459 Plantation Club - Quick walk to the Sea Pines Beach C...

Hilton Head Island
459 Plantation Club - Quick walk to the Sea Pines Beach Club - 3 BRs. These 3 Bedroom, 3.5 Bath spa...
Villa 3 / 4 / 9

*
Online booking available

$114 - $228
Per Night

$795 - $1795
Per Week

Evian 186

Hilton Head Island
2BD/2BA ground floor villa with golf & lagoon views. King, 2 Twin beds &Sleep Sofa. Pool & Tennis Co...
Villa 2 / 2 / 6

*
Online booking available

$155 - $230
Per Night

$775 - $1150
Per Week

Deluxe one bedroom oceanview condo

Hilton Head Island
Deluxe one bedroom oceanview condo Unit Description: This 500 sq. ft. one bedroom unit features a f...
Condo 1 / 1 / 6

*
Online booking available

$139 - $999
Per Night

$973 - $6993
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