Hilton Head Island Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

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

Beach Villa 9 -3 bedrooms Oceanside-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

$220 - $460
Per Night

$1100 - $2300
Per Week

Crown Reef 2 bed 2 bath villa minutes from the beach.

Hilton Head Island
Our relaxing 2 bedroom, 2 bath Crown Reef villa is a first floor end unit in family-centered Port Ro...
Villa 2 / 2 / 8

$111 - $154
Per Night

$780 - $1080
Per Week

105 Beachwalk-Fully 1st Floor. Quick walk to Beach Club &...

Hilton Head Island
105 Beachwalk-Fully 1st Floor. Quick walk to Beach Club & Fido Friendly This 1st floor 2 bedroom, 2...
Villa 2 / 2 / 6

*
Online booking available

$120 - $160
Per Night

$595 - $1631
Per Week

2 BR Oceanfront 2nd Floor Villa with Private Oceanfront B...

Hilton Head Island
2 BR Oceanfront 2nd Floor Villa with Private Oceanfront Balcony! **Shorewood 203** This lovely 2...
Villa 2 / 2 / 6

*
Online booking available

$270 - $475
Per Night

$1200 - $2800
Per Week

Beach Villa 13 - Oceanside Updated 3 Bedroom Townhouse

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

*
Online booking available

$220 - $460
Per Night

$1100 - $2300
Per Week

62 Night Heron-Fully renovated top/bottom, super Cute & Q...

Hilton Head Island
62 Night Heron-Fully renovated top/bottom, super Cute & Quick walk to beach Ideally located for a s...
Home 3 / 2 / 6

*
Online booking available

$180 - $220
Per Night

$895 - $2261
Per Week

Seascape Villa 3088-Beautifully Decorated, Relaxing Atmos...

Hilton Head Island
Seascape Villa 3088-Beautifully Decorated, Relaxing Atmosphere This nicely decorated villa has all ...
Condo 3 / 2 / 8

*
Online booking available

$132 - $267
Per Night

$745 - $1420
Per Week

Seaside Villa 268 - Nicely renovated oceanfront close to ...

Hilton Head Island
Seaside Villa 268 - Nicely renovated oceanfront close to dining & shopping Beautifully decorated, t...
Condo 1 / 1 / 6

*
Online booking available

$88 - $184
Per Night

$445 - $920
Per Week

Fabulous Top Floor Villa on the Beach with Sound/ Ocean V...

Hilton Head Island
Fabulous Top Floor Villa on the Beach with Sound/ Ocean Views at South Beach! **Beachside Tennis 18...
Villa 2 / 2 / 6

*
Online booking available

$250 - $400
Per Night

$1100 - $2750
Per Week

Hilton Head Island Villa

Hilton Head Island
Brigantine Quarters is located on the south end of Hilton Head Island in Shipyard Plantation with gr...
Villa 2 / 2 / 6

$700 - $900
Per Week

2-E Golfmaster-Pool and tennis courts on site! Quick bike...

Hilton Head Island
2-E Golfmaster-Pool and tennis courts on site! Quick bike ride to the beach. This charming 2nd floo...
Villa 3 / 3 / 8

*
Online booking available

$128 - $219
Per Night

$896 - $1724
Per Week

Courtside 107 - Updated Forest Beach Townhouse

Hilton Head Island
Courtside is an ocean-oriented complex with first-floor apartments, two-story and three-story townho...
Condo 2 / 2.5 / 7

*
Online booking available

$130 - $225
Per Night

$650 - $1125
Per Week

Sea Crest 2204 - Oceanview 2nd Floor Condo

Hilton Head Island
Stay in an exceptional 2nd floor oceanside condo within a newly built North Forest Beach oceanfront ...
Condo 2 / 2 / 6

*
Online booking available

$200 - $400
Per Night

$1000 - $2000
Per Week

Lake Forest 3304 - Sea Pines One Level Condo

Hilton Head Island
Lake Forest is a quiet community adjacent to the 600 acre Sea Pines Forest Preserve which features t...
Condo 2 / 2 / 6

*
Online booking available

$140 - $239
Per Night

$700 - $1195
Per Week

Hilton Head Beach Villa 23 - 3 BR 3 BA Oceanview Townhome

Hilton Head Island
23 Beach Villas is one of only 30 Villas in a complex situated on 6 acres of oceanfront property. Ex...
Condo 3 / 3 / 8

*
Online booking available

$187 - $474
Per Night

$1020 - $2370
Per Week

14 Collier Beach Road

Hilton Head Island
With a private pool & deck and boardwalk to the beach, this over-sized oceanfront house is just what...
Home 6 / 6 / 16

*
Online booking available

$820 - $2345
Per Night

$3570 - $16415
Per Week

Harbour Town Club 1265

Hilton Head Island
Harbour Town Club 1265 is a four bedroom town home located in the heart of Harbour Town in Sea Pines...
Villa 4 / 4 / 10

*
Online booking available

$260 - $1555
Per Night

$1295 - $7770
Per Week

Island Club 5402, 2 Bedroom, Oceanfront, Large Pool, Slee...

Hilton Head Island
Wake up to the sound of waves crashing ashore right off your condo balcony. That’s just one of a hun...
Condo 2 / 2 / 8

*
Online booking available

$197 - $394
Per Night

$1378 - $2756
Per Week

Bluff Villas 1657, Ground Floor, 2 Bedrooms, Pool, Sleeps 4

Hilton Head Island
This ground floor villa sleeps four in comfort and serenity. The beautiful furnishings, shady privat...
Condo 2 / 2 / 4

*
Online booking available

$134 - $279
Per Night

$937 - $1954
Per Week

3 BR Home plus Den, 2 Living Areas & Private Pool with Go...

Hilton Head Island
3 BR Home plus Den, 2 Living Areas & Private Pool with Golf Course View **Willow Oak 2** Situate...
Home 3 / 3.5 / 9

*
Online booking available

$350 - $700
Per Night

$1750 - $3500
Per Week

Southern Soleil

Hilton Head Island
Southern Soleil is located on a quiet street in Sea Pines Plantation, only 4 rows back from the beac...
Home 5 / 6 / 12

*
Online booking available

$475 - $1370
Per Night

$2870 - $8365
Per Week

Colonnade Club 143, 2 Bedrooms, Wifi, Pet Friendly, Sleeps 4

Hilton Head Island
Shipyard Plantation is one of Hilton Head’s most popular communities, with bike and walking trails, ...
Condo 2 / 2 / 4

*
Online booking available

$125 - $234
Per Night

$875 - $1638
Per Week

Top of the Morning, from the Top of Seacrest, #2513!

Hilton Head Island
Enjoy spectacular sunrises and ocean vistas from this top floor villa. This 2-bedroom, 2 bath villa ...
Villa 2 / 2 / 8

*
Online booking available

$220 - $540
Per Night

$1095 - $3087
Per Week

Seaside Villa 139 - Cozy with Great Ocean view, Close to ...

Hilton Head Island
Seaside Villa 139 - Cozy with Great Ocean view, Close to pool Seaside 139 is a nicely furnished vil...
Condo 1 / 1 / 4

*
Online booking available

$78 - $160
Per Night

$345 - $800
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