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

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

$116 - $149
Per Night

$495 - $1095
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

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 - $133
Per Night

$495 - $995
Per Week

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

Hilton Head Island
1 Collier Beach Road: 5 BR/ 6.5 BA, Sleeps 16, 215 feet to the beach First Floor: Living Area (Slee...
Home 5 / 6.5 / 16

*
Online booking available

$550 - $1250
Per Night

$3570 - $8750
Per Week

48 Hilton Head Cabana

Hilton Head Island
Welcome to 48 Hilton Head Cabana a beautiful ocean oriented 2 story townhome located in North Forest...
Home 2 / 2.5 / 4

*
Online booking available

$125 - $210
Per Night

$945 - $1470
Per Week

Xanadu 6-C, 1 Bedroom, Large Pool, Tennis, Walk to Beach

Hilton Head Island
Are you looking for a beautiful place to stay during your vacation to South Carolina? Look no furthe...
Condo 1 / 1 / 4

*
Online booking available

$110 - $219
Per Night

$595 - $1095
Per Week

3 Sweet Gum Court

Hilton Head Island
Welcome to 3 Sweet Gum Court located in the heart of Sea Pine Plantation! This wonderfully update s...
Home 3 / 3 / 8

*
Online booking available

$190 - $360
Per Night

$1330 - $2520
Per Week

Fern Court 7, 3 Bedrooms, Golf View, Large Pool, Sleeps 10

Hilton Head Island
Welcome to one of Sea Pine's most charming and spacious 3 bedroom, 3 bath vacation homes. Fern Court...
Home 3 / 3 / 10

*
Online booking available

$270 - $899
Per Night

$1350 - $4495
Per Week

Egret 5, Luxury 6 Bedroom, Elevator, Private Pool, Spa, S...

Hilton Head Island
5 Egret in North Forest Beach is a spacious and extraordinary 6 Bedroom/6.5 baths, over 4,000 square...
Home 6 / 6.5 / 20

*
Online booking available

$539 - $1431
Per Night

$2695 - $7155
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 - $183
Per Night

$695 - $1495
Per Week

38 Crabline Court- Near Ocean, Pet Friendly, Pool

Hilton Head Island
38 Crabline Court: 5 BR/ 4 BA, Sleeps 14, .6 miles to the beach   First Floor: Kitchen, Living, Din...
Home 5 / 4 / 14

*
Online booking available

$400 - $760
Per Night

$2800 - $5320
Per Week

Racquet Club Villas 2327

Hilton Head Island
This is a Pet Friendly Villa! (Dogs Only - Must Call for Details) This beautifully updated two bedr...
Villa 2 / 2 / 8

*
Online booking available

$155 - $450
Per Night

$805 - $2240
Per Week

Tennismaster 1102, 3 Bedroom, Large Pool, Walk to Beach, ...

Hilton Head Island
1102 Tennismaster is a bright and cheery, pet friendly, 3 bedroom, 3.5 bath townhome in Shipyard Pla...
Condo 3 / 3.5 / 8

*
Online booking available

$150 - $272
Per Night

$950 - $1906
Per Week

523 Plantation Club, Beautifully Renovated, Free Bikes, P...

Hilton Head Island
523 Plantation Club, Beautifully Renovated, Free Bikes, Pool, Pet Friendly Plantation Club is locat...
Villa 2 / 2 / 6

*
Online booking available

$116 - $500
Per Night

$595 - $2000
Per Week

Walk to Beach, Large Pool, Free Bikes, 33 Ocean Breeze

Hilton Head Island
Escape to the Beach! Looking for Value? You always get: 4 New Adult Aluminum Bikes with baskets, l...
Condo 3 / 3 / 8

*
Online booking available

$133 - $183
Per Night

$695 - $1495
Per Week

Lagoon Road 29, 4 Bedroom, Wooded View, Close to Beach, S...

Hilton Head Island
29 Lagoon Road in North Forest Beach is amazing! Located on a lagoon and only 2 blocks from the beac...
Home 4 / 3 / 10

*
Online booking available

$210 - $484
Per Night

$1050 - $2420
Per Week

2 Driftwood Lane

Hilton Head Island
Welcome to 2 Driftwood Lane, the home is only 100 steps from the beach and is on  a private lane in ...
Home 3 / 2.5 / 10

*
Online booking available

$325 - $645
Per Night

$2275 - $4515
Per Week

Canvas Back 12

Hilton Head Island
This is a Pet Friendly Home! (Dogs Only - Must Call for Details) This recently renovated home is on...
Home 5 / 4 / 14

*
Online booking available

$610 - $1275
Per Night

$3045 - $6405
Per Week

Plantation Club 528, 2 Bedroom, 2 Large Pools, Elevator, ...

Hilton Head Island
528 Plantation Club in Sea Pines Plantation is a charming and well appointed villa is close to every...
Condo 2 / 2 / 5

*
Online booking available

$150 - $290
Per Night

$750 - $1450
Per Week

St. Andrews Common 1657, Ground Level, 1 Bedroom, Pool, S...

Hilton Head Island
1657 St. Andrews Common in Palmetto Dunes. Step inside this fully renovated ground floor popular pet...
Condo 1 / 1.5 / 4

*
Online booking available

$119 - $230
Per Night

$595 - $1150
Per Week

New to Market, New Everything! Golf Views, Free Bikes, Po...

Hilton Head Island
New to Market, New Everything! Golf Views, Free Bikes, Pool Access. 24 Willow 3 Bedrooms, 3 Baths 1...
Home 3 / 3 / 8

*
Online booking available

$166 - $625
Per Night

$895 - $2500
Per Week

1 BR Villa in Sea Pines Walking Distance to the Beach & P...

Hilton Head Island
1 BR Villa in Sea Pines Walking Distance to the Beach & Pet Friendly! **Night Heron Villa 10** T...
Villa 1 / 1 / 4

*
Online booking available

$140 - $200
Per Night

$700 - $1050
Per Week

Evian 288, 3 Bedrooms, Golf & Lagoon View, Sleeps 8

Hilton Head Island
288 Evian in Shipyard Plantation is spacious and was recently renovated. This 3 bedroom villa includ...
Condo 3 / 3 / 8

*
Online booking available

$179 - $339
Per Night

$895 - $1695
Per Week

81 Ocean Breeze, All brand new furnishings. Free Bikes, p...

Hilton Head Island
81 Ocean Breeze, All brand new furnishings. Free Bikes, pool, tennis. Dogs Ok This unit is brand ne...
Condo 2 / 2.5 / 6

*
Online booking available

$99 - $133
Per Night

$495 - $995
Per Week

Plantation Club 490

Hilton Head Island
Golf Course Renovation through late September 2016 – Call Office for Details. This is a Pet Friendl...
Villa 3 / 3 / 6

*
Online booking available

$240 - $660
Per Night

$1260 - $3325
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