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

$99 - $133
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

$120 - $160
Per Night

$451 - $1519
Per Week

3 Wanderer Lane

Hilton Head Island
Welcome to 3 Wanderer Lane, a gorgeous elevated two story home that is only steps from the beach, lo...
Home 6 / 4.5 / 12

*
Online booking available

$425 - $1070
Per Night

$2975 - $7490
Per Week

Dune Lane 101

Hilton Head Island
This lovely oceanfront home offers a pool and spacious deck for enjoying life at the beach! The seco...
Home 5 / 4 / 12

*
Online booking available

$740 - $1850
Per Night

$3745 - $9275
Per Week

124 N Forest Beach Ct-Oceanfront, Pool & Hot Tub

Hilton Head Island
Beautiful oceanfront North Forest Beach home. This 6 bedroom, 6 ½ bath with *heated pool and hot tub...
Home 6 / 6.5 / 14

*
Online booking available

$760 - $760
Per Night

$3990 - $10299
Per Week

Pet Friendly 5th Row Ocean Home in Sea Pines w/ Pool Acce...

Hilton Head Island
Pet Friendly 5th Row Ocean Home in Sea Pines w/ Pool Access at South Beach **South Beach Lane 47** ...
Home 4 / 2 / 8

*
Online booking available

$310 - $475
Per Night

$1400 - $2200
Per Week

4 BR Home on the Ocean Side with Private Pool & Pet Friendly

Hilton Head Island
**Seaspray 1** This casual Beach House is just 2 houses from the Beach & offers a large Wrap Arou...
Home 4 / 3 / 10

*
Online booking available

$375 - $520
Per Night

$1700 - $3750
Per Week

Greens 194, Updated 2 Bedrooms, Large Pool, Golf View, Sl...

Hilton Head Island
194 The Greens in Shipyard Plantation has had the entire first level completely renovated. All new k...
Condo 2 / 2.5 / 7

*
Online booking available

$133 - $262
Per Night

$928 - $1831
Per Week

3 Scaup - Quick walk to the beach & to South Beach Marina

Hilton Head Island
This charming 3 bedroom, 3 bathroom vacation home is located in the South Beach area of Sea Pines. *...
Home 3 / 3 / 8

*
Online booking available

$240 - $240
Per Night

$1199 - $4095
Per Week

Village House 102, 2 Bedrooms, Pet Friendly, Pool, Sleeps 6

Hilton Head Island
102 Village House in Port Royal Plantation. Welcome to this exquisite first-floor condo (elevated 1 ...
Condo 2 / 2 / 6

*
Online booking available

$125 - $236
Per Night

$875 - $1654
Per Week

Sea Oak Lane 05

Hilton Head Island
This second row vacation home has a spacious floor plan and is located in a great spot on the island...
Home 5 / 4 / 12

*
Online booking available

$470 - $1220
Per Night

$2380 - $6090
Per Week

13 Sandpiper Street

Hilton Head Island
Relax at this beachside bungalow under the huge Spanish mossed draped oak. Cool off in a private poo...
Home 3 / 2 / 8

*
Online booking available

$355 - $610
Per Night

$2485 - $4270
Per Week

Singleton Beach 11A, Oceanfront, 2 Bedrooms, Elevator, Pool

Hilton Head Island
11A Singleton Place in Singleton Beach is 2 bedroom oceanfront villa. Located in the exclusive commu...
Home 2 / 2 / 6

*
Online booking available

$330 - $859
Per Night

$2310 - $6013
Per Week

71 Heritage Road

Hilton Head Island
Welcome to 71 Heritage Road located in the heart of Sea Pines Plantation! This beautiful single flo...
Home 3 / 2 / 8

*
Online booking available

$255 - $475
Per Night

$1785 - $3325
Per Week

91 Kingston Dunes, 3 Bedrooms, Private Pool, Pet Friendly...

Hilton Head Island
If you’re looking for a freestanding home with a private pool and close proximity to golf courses an...
Home 3 / 3 / 6

*
Online booking available

$207 - $585
Per Night

$1450 - $4096
Per Week

114 Beachwalk - 3 Minutes walk to the beach & Tennis

Hilton Head Island
Within earshot of the rolling surf, this 1 bedroom, 2 bath is a charming villa across from the Sones...
Villa 1 / 2 / 4

*
Online booking available

$120 - $120
Per Night

$387 - $1302
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

4 Hilton Head Cabana

Hilton Head Island
This wonderful 2 story villa is located at 4 Hilton Head Cabana which is located in the South Forest...
Villa 2 / 1.5 / 4

*
Online booking available

$115 - $190
Per Night

$805 - $1330
Per Week

35 Bradley Beach-Bring Fido! Steps to the Beach & Dog Park.

Hilton Head Island
Pet-friendly* 4 bedroom, 3 bath home, with private pool located in the Bradley Beach area of Hilton ...
Home 4 / 3 / 10

*
Online booking available

$240 - $240
Per Night

$1050 - $3002
Per Week

Racquet Club Villas 2340

Hilton Head Island
Racquet Club Villa 2340 is a two bedroom villa located just a short walk from Harbour Town in Sea Pi...
Villa 2 / 2 / 6

*
Online booking available

$125 - $430
Per Night

$665 - $2135
Per Week

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

Hilton Head Island
This lovely villa near the beach has a balcony with beautiful forest views, TVs in every room, and t...
Condo 2 / 2 / 7

*
Online booking available

$125 - $259
Per Night

$891 - $891
Per Week

St. Andrews Common 1664, 1 Bedroom & loft, Large Pool, Sl...

Hilton Head Island
1664 St. Andrews in Palmetto Dunes. This 2nd-floor pet-friendly villa has a brand new living room wi...
Condo 2 / 2 / 8

*
Online booking available

$108 - $209
Per Night

$758 - $1464
Per Week

St. Andrews Common 1861, 2 Bedroom, Pet Friendly, Sleeps 6

Hilton Head Island
1861 St. Andrews in Palmetto Dunes. What a positively delightful, charming and whimsical 1BR, 1 Loft...
Condo 2 / 2 / 6

*
Online booking available

$108 - $209
Per Night

$758 - $1464
Per Week

Evian 135, 2 Bedroom, Golf Views, Pool, Pet Friendly, Sle...

Hilton Head Island
Surround yourself with elegant furnishings and lush garden views in this European-inspired unit. You...
Condo 2 / 2 / 6

*
Online booking available

$116 - $219
Per Night

$811 - $1531
Per Week

Pet Friendly Townhouse with Partial Golf Views & Pool on ...

Hilton Head Island
Pet Friendly Townhouse with Partial Golf Views & Pool on Site. **Shipmaster 604** This charming ...
Villa 2 / 2.5 / 5

*
Online booking available

$190 - $300
Per Night

$850 - $1300
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