Hilton Head Island Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

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

Captains Walk 481

Hilton Head Island
2 BD/2 BA fifth floor oceanfront villa. King and 2 Twin beds. (Sleep sofa linens provided for addit...
Villa 2 / 2 / 6

*
Online booking available

$220 - $440
Per Night

$1100 - $2200
Per Week

Pelican 7

Hilton Head Island
4 BD/3 Ba 2-level home. King, Queen, 2 Fulls & 2 Twins. Sleep sofa. Private Pool* & Hot Tub* (*c...
Home 4 / 3 / 12

*
Online booking available

$400 - $880
Per Night

$2000 - $4400
Per Week

Beachside Tennis 1854

Hilton Head Island
2BD/2BA second floor villa overlooking pool & beach. King & 2 Queen beds.Multiple TV's & FREE WIFI. ...
Villa 2 / 2 / 6

*
Online booking available

$220 - $440
Per Night

$1100 - $2200
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 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

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

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

Hilton Head Island
<div id="TA_vrbadge310" class="TA_vrbadge"> <ul id="RQdGTS" class="TA_links vRfrSsjc"> &...
Home 4 / 3 / 12

$1500 - $5800
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

South Beach Club 1905

Hilton Head Island
3 BD/2.5 BA 1st floor villa with Pool & Sound views. King, Queen, & 2 Twins. 1 HR/Day free tennis...
Villa 3 / 2 / 6

*
Online booking available

$260 - $530
Per Night

$1300 - $2650
Per Week

Shorewood 136

Hilton Head Island
2 BD / 2 BA ocean view villa. King, Queen & Twin bed. Sleep sofa. Pool, Hot Tub & Baby Pool on site....
Villa 2 / 2 / 7

*
Online booking available

$220 - $400
Per Night

$1100 - $2000
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

313 Breakers

Hilton Head Island
Recently renovated, this 1 bedroom, 1 bath OCEANFRONT villa has everything you'll want for a perfect...
Villa 1 / 1 / 4

*
Online booking available

$71 - $142
Per Night

$495 - $1195
Per Week

Courtside 100 - Forest Beach 1st Floor Flat

Hilton Head Island
Courtside is an ocean-oriented complex with first-floor apartments, two-story and three-story townho...
Condo 2 / 2 / 6

*
Online booking available

$140 - $199
Per Night

$695 - $995
Per Week

Shorewood 332 - Oceanview 3rd Floor Condo

Hilton Head Island
With a balcony accessible by the living room and master bedroom, guests staying in Shorewood 332 enj...
Condo 2 / 2 / 6

*
Online booking available

$215 - $359
Per Night

$1075 - $1795
Per Week

Courtside 86 - 3 Bedroom Townhouse- New Unit

Hilton Head Island
Courtside is an ocean-oriented complex with a beautiful landscaped courtyard, lagoon and large pool ...
Condo 3 / 4 / 8

*
Online booking available

$190 - $279
Per Night

$950 - $1395
Per Week

104 Northshore Place-100 yrds to the beach, 2 BR villa. 2...

Hilton Head Island
104 Northshore Place-100 yrds to the beach, 2 BR villa. 2014 weeks avail Beautiful, new, ocean-orie...
Villa 2 / 2 / 6

*
Online booking available

$85 - $199
Per Night

$595 - $1595
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

3 Scaup - Cute 3 BR Home, close to S. Beach & quick walk ...

Hilton Head Island
3 Scaup - Cute 3 BR Home, close to S. Beach & quick walk to the beach. This charming 3 bedroom, 3 b...
Home 3 / 3 / 6

*
Online booking available

$171 - $171
Per Night

$1195 - $3195
Per Week

Shorewood 131 - Oceanside 1st Floor Condo

Hilton Head Island
Stay ocean-side and enjoy many benefits of an oceanfront complex without paying oceanfront prices. G...
Condo 2 / 2 / 6

*
Online booking available

$200 - $315
Per Night

$995 - $1575
Per Week

48 Kingston Road - Cute & Renovated 3 BR Home w/ Private ...

Hilton Head Island
48 Kingston Road - Cute & Renovated 3 BR Home w/ Private Pool - Sleeps 6 WHAT COULD YOU BE WAITING ...
Home 3 / 3 / 6

*
Online booking available

$142 - $142
Per Night

$995 - $2795
Per Week

6 Turtle Lane - Pretty 3 BR Townhouse- Some winter weeks ...

Hilton Head Island
6 Turtle Lane - Pretty 3 BR Townhouse- Some winter weeks left. Book Now Located in the Oceanfront c...
Villa 3 / 3 / 6

*
Online booking available

$156 - $156
Per Night

$1095 - $2795
Per Week

233 Beachside Home-4 BR / renovated & additional 1000 sq ...

Hilton Head Island
233 Beachside Home-4 BR / renovated & additional 1000 sq ft added. WOW... describes this 2 story 4 ...
Home 4 / 5 / 10

*
Online booking available

$171 - $171
Per Night

$1195 - $3195
Per Week

222 Shorewood - Fully renovated 3 BR courtyard to pool view.

Hilton Head Island
Fantastic newly redecorated 3 bedroom Shorewood Villa! This villa has had a complete overhaul with n...
Villa 3 / 3 / 8

*
Online booking available

$128 - $128
Per Night

$895 - $2295
Per Week

Courtside 43 - Forest Beach 1st Floor Flat

Hilton Head Island
Courtside is an ocean-oriented complex with first-floor apartments, two-story and three-story townho...
Condo 2 / 2 / 6

*
Online booking available

$140 - $199
Per Night

$695 - $995
Per Week

Springwood 26 - Forest Beach Townhouse

Hilton Head Island
Springwood is an ocean-oriented complex with first-floor apartments and townhouses. Springwood 26 is...
Condo 3 / 4 / 6

*
Online booking available

$175 - $255
Per Night

$875 - $1275
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