Hilton Head Island Vacation Rental Getaways


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Sort by: Type BR/BA/Sleeps Price

5403 Treetops, Renovated 2 BR Villa, Free Bikes, Pool, Te...

Hilton Head Island
5403 Treetops, Renovated 2 BR Villa, Free Bikes, Pool, Tennis, Beach Call for Reservations - Brad: ...
Villa 2 / 2.5 / 6

*
Online booking available

$85 - $114
Per Night

$495 - $995
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 This 1st floor 2 bedro...
Villa 2 / 2 / 6

*
Online booking available

$160 - $160
Per Night

$623 - $1617
Per Week

St. Andrews Place 11

Hilton Head Island
This beautiful home is nestled on the lagoon in Sea Pines and offers partial views of the Harbour To...
Home 4 / 3 / 14

*
Online booking available

$380 - $1545
Per Night

$1925 - $7735
Per Week

606 Queens Grant

Hilton Head Island
Welcome to 606 Queens Grant located in Palmetto Dunes Plantation! The villa is a single story, an o...
Home 2 / 2 / 4

*
Online booking available

$120 - $160
Per Night

$840 - $1120
Per Week

Beachside 4, 4 Bedrooms, Pool Access, Sea Pines Sleeps 10

Hilton Head Island
This stunning unit features a large deck, a backyard patio, two private balconies, and a TV in every...
Home 4 / 4 / 10

*
Online booking available

$266 - $1176
Per Night

$1823 - $4043
Per Week

5301 Treetops, Renovated 2 Bedroom Villa, Pool, Tennis, B...

Hilton Head Island
A 2-bedroom, 2.5-bathroom condo, 5301 Treetops is an ideal home base for your next family vacation. ...
Condo 2 / 2.5 / 6

*
Online booking available

$125 - $236
Per Night

$875 - $1654
Per Week

Luxury Harbour Town 5Br w/ Private Deck & Lounging Pool -...

Hilton Head Island
Luxury Harbour Town 5Br w/ Private Deck & Lounging Pool - Water Views PROPERTY OVERVIEW Located i...
Home 5 / 4.5 / 15

*
Online booking available

$445 - $750
Per Night

$3088 - $5247
Per Week

Award-Winning Palmetto Dunes 6Br w/ Private Pool, Hot Tub...

Hilton Head Island
Award-Winning Palmetto Dunes 6Br w/ Private Pool, Hot Tub & Multiple Decks Enjoy a luxurious beach ...
Home 6 / 6.5 / 17

*
Online booking available

$548 - $1448
Per Night

$3817 - $10136
Per Week

7 Abalone Lane

Hilton Head Island
This home is a grand fourth row home that will make you question leaving, even if it is a short 4 mi...
Home 5 / 6 / 16

*
Online booking available

$595 - $1300
Per Night

$2520 - $9100
Per Week

16 Sea Oak Lane

Hilton Head Island
Welcome to 16 Sea Oak Lane, a gorgeous 2 story oceanfront home located in South Forest Beach! This ...
Home 6 / 6 / 14

*
Online booking available

$560 - $1610
Per Night

$3920 - $11270
Per Week

Slack Tide 6, 4 Bedrooms, Lagoon View, Pet Friendly, Slee...

Hilton Head Island
6 Slack Tide, Palmetto Dunes features 4 bedrooms and awesome views of the lagoon! Bring your fishing...
Home 4 / 3.5 / 11

*
Online booking available

$249 - $616
Per Night

$1744 - $4315
Per Week

St. Andrews Common 1658, 1 Bedroom, Large Pool, Ground Fl...

Hilton Head Island
With a location that’s close to everything you want to do on Hilton Head Island, St. Andrews Common ...
Condo 1 / 1.5 / 4

*
Online booking available

$99 - $201
Per Night

$694 - $1409
Per Week

11 Hilton Head Cabanas

Hilton Head Island
This adorable two bedroom, one and a half bathroom villa is the perfect getaway for couples and smal...
Villa 2 / 1 / 6

*
Online booking available

$135 - $190
Per Night

$875 - $1330
Per Week

3 BR/ 3 Bath, 2nd floor Pet Friendly Villa with Pool & Sp...

Hilton Head Island
3 BR/ 3 Bath, 2nd floor Pet Friendly Villa with Pool & Spa on site. **Colonnade Club 196** Situa...
Villa 3 / 3.5 / 6

*
Online booking available

$230 - $400
Per Night

$1000 - $2000
Per Week

Beachwalk 186, 1 Bedroom, Pool, Near Beach, Sleeps 4

Hilton Head Island
186 Beachwalk, Shipyard Plantation. This very attractive 1BR/2 full bath, second-floor Beachwalk vil...
Condo 1 / 2 / 4

*
Online booking available

$108 - $209
Per Night

$758 - $1464
Per Week

Updated 3Br Villa w/ En-Suite Baths - Walk to Beach, Pool...

Hilton Head Island
Updated 3Br Villa w/ En-Suite Baths - Walk to Beach, Pools, Tennis Set in the sought-after Ocean Br...
Condo 3 / 3 / 8

*
Online booking available

$171 - $224
Per Night

$1198 - $1566
Per Week

Oversized 2 Bd Jewel, Free Bikes & Tennis, Pet Friendly, ...

Hilton Head Island
Oversized 2 Bd Jewel, Free Bikes & Tennis, Pet Friendly, Walk 2 Beach & Pool Call for Reservations ...
Villa 2 / 2 / 6

*
Online booking available

$114 - $156
Per Night

$695 - $1395
Per Week

Golfmaster 304, 2 Bedrooms, Large Pool, Tennis, Sleeps 10

Hilton Head Island
304 Golfmaster in Shipyard Plantation is located near the Clipper Golf Course. This 2 bedroom, 2.5 b...
Condo 2 / 2.5 / 10

*
Online booking available

$104 - $209
Per Night

$729 - $1464
Per Week

Queens Grant 765

Hilton Head Island
Queens Grant 765 is a lovely three bedroom villa, with updates throughout and an expansive deck over...
Villa 3 / 3 / 6

*
Online booking available

$160 - $350
Per Night

$805 - $1750
Per Week

Wendover Dunes 8136

Hilton Head Island
Wendover Dunes 8136 is a second floor, two bedroom condo just steps away from the beach in Palmetto ...
Condo 2 / 2 / 8

*
Online booking available

$190 - $490
Per Night

$980 - $2450
Per Week

2 Collier Beach Road

Hilton Head Island
This home in Singleton Beach is a wonderful oceanfront 5 Bedroom/5.5 Bathroom home with an oceanfron...
Home 5 / 5.5 / 14

*
Online booking available

$710 - $1965
Per Night

$3045 - $13755
Per Week

St. Andrews Common 1758, End Unit, 2 Bedrooms, Pool, Slee...

Hilton Head Island
This popular townhome books up fast, and for good reason. St. Andrews Common 1758 is ideally located...
Condo 2 / 2 / 7

*
Online booking available

$125 - $227
Per Night

$875 - $1586
Per Week

2 Oleander, 3 Bedrooms, Pet Friendly, Private Pool, Sleeps 7

Hilton Head Island
You’ll enjoy the best of Hilton Head Island when you vacation at 2 Oleander, a home with a private p...
Home 3 / 2 / 7

*
Online booking available

$242 - $585
Per Night

$1692 - $4096
Per Week

Henry Lane 11, 4 Bedroom, Private Heated Pool, Walk to Be...

Hilton Head Island
Henry Lane 11 is a wonderful 4 bedroom house with a private Heated pool in Singleton Beach in the ne...
Home 4 / 4.5 / 14

*
Online booking available

$228 - $697
Per Night

$1595 - $4881
Per Week

Racquet Club Villas 2327

Hilton Head Island
This beautifully updated two bedroom villa overlooks the lagoon and is conveniently located close to...
Villa 2 / 2 / 8

*
Online booking available

$145 - $410
Per Night

$735 - $2065
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