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

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

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

$89 - $133
Per Night

$495 - $995
Per Week

Seaside Villa 268 - 1 BR 1 BA Oceanfront Flat Hilton Head...

Hilton Head Island
Seaside Villa 268 - 1 BR 1 BA Oceanfront Flat Hilton Head, Sc Beautifully decorated, this one bedro...
Condo 1 / 1 / 6

*
Online booking available

$88 - $184
Per Night

$445 - $920
Per Week

3 BR, 2 bath Seascape Villa 3088 - courtyard view, nicely...

Hilton Head Island
3 BR, 2 bath Seascape Villa 3088 - courtyard view, nicely decorated This nicely decorate villa has ...
Condo 3 / 2 / 8

*
Online booking available

$107 - $167
Per Night

$620 - $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

$220 - $400
Per Night

$1100 - $2400
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 - $180
Per Night

$725 - $2414
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

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

$200 - $440
Per Night

$1000 - $2200
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

$120 - $160
Per Night

$506 - $1689
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

$240 - $350
Per Night

$1200 - $2500
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

$200 - $440
Per Night

$1000 - $2200
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 7148H 2 Bedrooms, 2 Bathrooms,...
Villa 2 / 2 / 8

*
Online booking available

$104 - $149
Per Night

$495 - $1095
Per Week

1 Bedroom Oeanside Seaside Villa, Hilton Head, Sc

Hilton Head Island
Pictures coming Villa 162 is a nicely decorated ocean side condo with a spectacular view of the bea...
Condo 1 / 1 / 6

*
Online booking available

$78 - $113
Per Night

$345 - $620
Per Week

2 bedroom, 1 bath Sands Village

Hilton Head Island
Welcome to Sands Village!! Looking for a peaceful beach get away that?s within close walking distan...
Villa 2 / 1 / 6

*
Online booking available

$88 - $129
Per Night

$520 - $725
Per Week

Courtside 95 - Close to the beach - Large 2 BR 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 - $219
Per Night

$650 - $1095
Per Week

Ocean One 120 - Beachside Condo-Kitchen Reno in 2017

Hilton Head Island
Ocean One 120 remodeled the kitchen in March/April 2017, with new cabinets, granite counters, and Bl...
Condo 2 / 2 / 6

*
Online booking available

$175 - $330
Per Night

$875 - $1650
Per Week

Ocean One 419 -Updated Lovely Oceanfront 4th Floor Condo

Hilton Head Island
Ocean One 419 is OCEAN FRONT on the FOURTH FLOOR of a five story elevator building. This 3 bedroom ...
Condo 3 / 3 / 10

*
Online booking available

$270 - $595
Per Night

$1350 - $2975
Per Week

Penthouse 5 at Seacrest - Oceanfront 4 BRs & Beautiful - ...

Hilton Head Island
Penthouse 5 at Seacrest - Oceanfront 4 BRs & Beautiful - Sleeps 10 SeaCrest Penthouse 5 is a stunni...
Villa 4 / 4 / 10

*
Online booking available

$440 - $660
Per Night

$2127 - $6849
Per Week

307 Shorewood -Direct Oceanfront with Beautiful Pool, Spa...

Hilton Head Island
307 Shorewood -Direct Oceanfront with Beautiful Pool, Spa & Kiddy Pool Stunning views from this ama...
Villa 3 / 3 / 8

*
Online booking available

$260 - $420
Per Night

$1355 - $4092
Per Week

12 Greenwing Teal - Oceanviews & Fully Renovated

Hilton Head Island
Renovated in the spring of 2016 this 2nd-row Sea Pines home is the very best in coastal living! 4 Be...
Home 4 / 3 / 11

*
Online booking available

$420 - $420
Per Night

$2189 - $7710
Per Week

New to Market, Breakers Villa. Sleeps 4, Free Wifi Beachf...

Hilton Head Island
New to Market, Breakers Villa. Sleeps 4, Free Wifi Beachfront Pool 304Br One of the best values in ...
Villa 1 / 1 / 4

*
Online booking available

$94 - $175
Per Night

$562 - $1050
Per Week

324 Breakers, Ocean Front! Free Bikes, Relax in Paradise.

Hilton Head Island
Watch the activity on the ocean, beach and pool from the convenience of your third-floor living room...
Villa 1 / 1 / 5

*
Online booking available

$109 - $154
Per Night

$653 - $1150
Per Week

1464 Sound Villa - Fully Renovated - Gorgeous views of th...

Hilton Head Island
1464 Sound Villa - Fully Renovated - Gorgeous views of the Calibogue Sound! 1464 Sound Villa was co...
Villa 5 / 4 / 14

*
Online booking available

$340 - $420
Per Night

$1750 - $4808
Per Week

Captain's Walk 467

Hilton Head Island
Captain's Walk 467 is an oceanfront, two-bedroom condo located Palmetto Dunes. This condo is located...
Villa 2 / 2 / 8

*
Online booking available

$280 - $605
Per Night

$1400 - $3045
Per Week

Village House 307, 2 Bedrooms, Pet Friendly, Elevator, Sl...

Hilton Head Island
307 Village House in Port Royal Plantation is an attractive 2 bedroom 2 bath, 3rd floor, with elevat...
Condo 2 / 2 / 8

*
Online booking available

$113 - $250
Per Night

$1075 - $1075
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