Hilton Head, SC Vacations

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Featured Vacation Rentals

Dreamy Island Condo W/ Beach Access, Sha...

Breakers 306Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If a beach vacation to the sun and fun of Hilton Head Island is what you are after, look no...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Pet Friendly 4 bedroom/4 bathroom townho...

1262 Harbour Town Club is a four bedroom town home located in the heart of Harbour Town in Sea Pines. The roomy living room has wood floors, flat screen TV and access to the private deck. The kitchen is entirely-equipped and opens up to the dining...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Beach Blossom - PET FRIENDLY PRIVATE HOM...

Stunning 3 Bedroom 2 Bathroom home located off Folly Field Rd. Beach Blossom has just been completely modernized and designer decorated. Upon entry you will be greeted by a completely furnished living room with vinyl floor throughout, and a mounted...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
497 Captains Cove is a lovely property l...

This gorgeous Captains Cove unit is the ideal will be the top of your list for your next stay!A short flight of stairs leads to a shady front porch, ideal resting place after your walk home from the beach. Enter into a huge, bright, open floor plan...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Serene Oceanfront Villa with WiFi, Pool,...

Island Club 2201Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beautiful ocean vistas along with a shining pool complex and multiple tennis courts are among...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Amazing golf views from almost every roo...

This comfortable end unit Hilton Head Island villa has tons of light with great vistas of the tee and greens at the Robert Trent Jones golf course. It also has the benefit of being close to the beach so you can comfortably walk or bicycle for a day...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Holiday Harbor at The Landing

duration: 4 hours max_age: 101 group_size: 50 description: Celebrate the start of the holiday season where the magic meets the water at Saluda Lake Holiday Harbor! Enjoy festive lakeside fun including holiday crafts, a build-your-own hot chocolate...

The Standard

Island Segway

Book online
$79.00

Explore Hilton Head Island by Land! Duration 1.5 Hours About Explore Hilton Head Island in style with this Island Segway tour! This 1.5 hour tour cruises down charming bike paths and boardwalks through Three beautiful parks to Hilton...

1 Week Rental

Island Life Rentals and Tours

Book online
$33.00 - $235.00

___________________________________ Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles...

Public Tours

Oh Snap

Book online
$15.00 - $20.00

Let's Adventure! Duration 45 Minutes About Come enjoy our incredible selfie museum with friends and family!

Lowcountry Lunch Cruise (Outside Dining)
Book online
$40.00 - $69.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Not wheelchair accessible description: ![Description of image](https://cdn.filestackcontent.com/bnLlDRzMSPaudj3mMT5x) Book Online and Skip the...

Day with a Native - Kahuna

Native Son Adventures

Book online
$365.00 - $1,260.00

Duration 3 to 8 Hours (prices may be subject to change due to rising fuel prices) Create your own amazing adventures or choose from our time tested favorites. Some favorite trips: 1.CREATE YOUR OWN DAY! Try some different...

Outdoor After School

Hilton Head Island Recreation Association

Book online
$150.00 - $800.00

duration: 4 Weeks • 2 Days Per Week meeting_point: Island Recreation Center min_age: 7 max_age: 14 group_size: Up to 20 Campers description: This is an after-school program hosted by Outdoor Rec where kids ages 7-14 can receive assistance...

Flyboard 40 Minute

Carolina Hydrofly

Book online
$139.00

40 Minute Flyboard Pro Series Experience About Each guest will have 30 minutes of flight time and 10 minutes of instruction time. If you would like to book for more than one person, then please process one booking per person by selecting the...

May River Ecology Excursion

May River Excursions

Book online
$40.00 - $50.00

*Learn about the ecosystem and wildlife of the May River!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ Duration 1.5...

Monkey Safari

Hilton Head Helicopter Tours

Book online
$369.00

Come see this magnificent fort, beaches and property from the air! Duration - **45 minutes** About - Along the way you will see old lighthouses, breath-taking coastal views of the Low Country, and small remote islands only few have ever...

Gift Card

Anchors Away Sailing Charters

Purchase a gift card for a friend!

Day Trip to Savannah

Flip Flop Charters

Book online
$525.00 - $1,150.00

Cruise to Savannah! Duration - 5 hours - 6 hours About Avoid the traffic and cruise to Savannah in style. We’ll take you through the backwaters into the Savannah River and dock right on river street. You’ll be right at the heart of all...

Hilton Head, SC

Hilton Head Island is a resort destination on the South Carolina coast known for its pristine beaches, world-class golf courses, and natural Lowcountry beauty.

Located just north of Savannah, Hilton Head combines upscale amenities with a relaxed island atmosphere. The island features 12 miles of wide sandy beaches, extensive bike trails, and a variety of outdoor activities including kayaking, dolphin cruises, and nature tours. Visitors can explore iconic spots like Harbour Town Lighthouse, enjoy local seafood at waterfront restaurants, or spend the day shopping and sightseeing in one of the island's many charming villages.

Hilton Head is home to a wide range of lodging options, including vacation rental homes, oceanfront resorts, and golf villas. The island is perfect for families, couples, and anyone looking for a mix of relaxation and recreation. Whether you're teeing off on a championship course, biking beneath moss-draped oaks, or simply soaking up the sun on the beach, Hilton Head offers a polished and peaceful coastal escape with something for everyone.

Hilton Head Island is arguably one of the most popular beach towns along the southern Carolina coast, with world class resorts and vacation rentals, gorgeous beaches, and plenty of entertainment available both on and off the beach. A regular on national "Top Ten Vacation Destination" lists, the island has an elite resort town feel that can easily cater to a wide range of tastes and interests.

Hilton Head SC

Boating, fishing, golfing, tennis, swimming, shopping, dining, and historical touring are all readily available in this somewhat small isle, and is all located within a 15 or 20 minute drive from any point in town. With luxurious amenities and accommodations, plenty of art and historical attractions, and even its own Symphony Orchestra, Hilton Head Island essentially takes the concept of an elite vacation retreat to an entirely elevated level.

Hilton Head SC

Hilton Head Island is one of the southernmost seaside isles along the South Carolina coastline and is located just a few minutes away from the Georgia state border. Separated from the mainland via the Calibogue Sound, the relatively wide island is a unique mixture of varying coastal landscapes, including ocean and sound facing beaches, with miles of rugged maritime forest in between. Because of this, even the most expansive resorts have a feel of relative privacy about them, as virtually every side street is lined with towering oaks, cedars, pines, and other evergreen foliage. The island is a total of 69 square miles, which includes roughly 28 square miles of water, but feels relatively small, as virtually any point can be easily reached via the William Hilton Parkway which circles through the interior of the island.

Hilton Head SC

Hilton Head has always been a popular destination, it seems, as archeologists have found ancient trash heaps that date back 4,000 to 15,000 years to the island's first native residents. Hilton Head did not garner international attention until 1521, when a Spanish New World exploration landed and began making friendly relations with the local inhabitants. The English Captain William made a more lengthy exploration in 1663, essentially re-discovering the area and its alluring proximity to Port Royal Sound, and naming the area "Hilton Head," after himself.

Hilton Head SC

Over the next several centuries, parcels of the island would be granted or purchased by new North American settlers, and the region would flourish as a site for Sea Island Cotton and Indigo plantations. A small chapel was constructed, the Zion Chapel of Ease, for the convenience of the newly wealthy plantation owners, and hundreds of slaves were brought to the area to tend the expansive farms. When the Civil War began, Union forces, recognizing the prime locale of Hilton Head directly in between the main southern ports of Savannah and Charleston, attacked the area with 12,000 troops, successfully overtaking the region on November 7th, 1861, and maintaining control of the territory for the duration of the war.

Hilton Head SC

Shortly after the battle, the Union forces freed the hundreds of slaves who lived and worked on the island, making them the first slaves that were freed during the war, and the first pioneers of a new, solely freed-slave village called Mitchelville. Four forts were constructed on the island, and while these Union strongholds are long gone, visitors can still visit the discreet remnants of Fort Howell and Fort Mitchel while touring the island.

Hilton Head SC

Life was quiet for the next few decades after the war, until 1931 when a Wall Street Tycoon purchased 17,000 acres of the island as a private gaming reserve. This purchase would prove to be prophetic, as in the decades that followed, the town would grow exponentially to accommodate the growing elite group of guests. This growth arguably didn't really begin until 1956, when the two-lane toll swing bridge, the James F. Byrnes Bridge, was built to allow vehicular traffic to the island for the first time, and a local developer, Charles E. Fraser, began the construction of the Sea Pines Resort.

Today, Hilton Head Island is a sprawling, but never overcrowded, collection of elite resorts, vacation rentals, hotels, and all the standard vacation amenities that an elite destination requires. Best of all, with historic attractions like the Zion Cemetery and Baynard Mausoleum, and the Mitchelville Freedom Park, visitors can always revisit Hilton Head's long and storied past.

Day-trippers will find a number of public accesses to pay a visit to Hilton Head's renowned shorelines, including Folly Field Beach Park, Driessen Beach Park, and Coligny Beach Park. While the beaches certainly claim the lion's share of admiration and attention, Hilton Head Island also has a number of attractions off the shore that will appeal to visitors of all ages.

Kids love exploring the Adventure Cove Family Fun Center and The Sandbox Interactive Children's Museum, while visitors of all ages can easily enjoy the Coastal Discovery Museum, the Baynard Plantation Ruins, and the Harbour Town shopping, dining and water sports complex, which is also home to the famed Hilton Head Lighthouse.

When it comes time to eat, vacationers will find hundreds of options that range from exquisite five star eateries to classic cafes and sandwich shops, and everything in between. Hilton Head Island is especially known for its waterfront dining options, and visitors will find gorgeous sunset-front establishments throughout the region.

There are just as many options when it comes to accommodations, as Hilton Head is home to a wide range of hotels, resorts, and weekly vacation rentals. The hotels and resorts are, for the most part, all-inclusive, with expansive private pools, golf courses, spas, and wide private beaches to entice guests, while the vacation rentals can range from small villas and condos to expansive 6 or 7 bedroom beachside estates. Clearly, every party size and expectation can be easily met, and potential vacationers will have a hard time determining where to stay on the island for a relaxing retreat.

Hilton Head Island has arguably been a popular destination for hundreds and even thousands of years, and it won't take new visitors very long to figure out why. With ample white sand beaches, cool shopping options, exceptional restaurants, and a world of attractions around every shaded street corner, it's easy to enjoy an activity-packed but incredibly fun and relaxing vacation. A favorite destination along South Carolina, Hilton Head continues to maintain its longstanding reputation as one of Coastal Carolina's most accommodating and luxurious retreats.

Hilton Head Vacation Guides