Hilton Head, SC Vacations

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Featured Vacation Rentals

Sea Pines - Newly Renovated - Greenwood ...

Dewberry Lane 17Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your days cycling along shaded leisure trails, perfecting your swing on world-class golf...

  • Hilton Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Total renovation June 2024, views, pool,...

Anchorage 7473Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This condo is located harborside in the fashionable Anchorage Villas. Spend blue-sky days at the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Spacious Deck, Hot Tub,  Second Row To B...

Sea FrontOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A special vacation to Hilton Head Island awaits you here at Sea Front, a excellent family-friendly...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Dog Friendly Home Near Golf & Beach with...

Summary:Queens Grant 653The Space:Absolutely filled with beachy appeal and all of the amenities of home, this island hideaway will be just the place to bring the whole family for an memorable vacation to the sunshine and salty air of Hilton Head...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Beautiful home on the 11-mile lagoon sys...

Come appreciate this enormous five bedroom and five bathroom home located on Palmetto Dunes' 11-mile lagoon system! Located within the heart of Palmetto Dunes Oceanfront Resort, this home has been attractively decorated throughout with wood floor...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Oceanview condo with pool, hot tub & ful...

Summary:Island Club 3303The Space:Appreciate this year-round Island Club destination with many amenities, including nine tennis courts, a shared lap pool, hot tub, kids’s pool, basketball court, and an broad exercise center. This two-bedroom...

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

Hilton Head Tours & Activities

Island Happy Hour Cruise

Daniel Island Ferry

Book online
$18.00 - $38.00

duration: 75 minutes meeting_point: description: Friday Happy Hour Cruise on the Wando River Every Friday | 4:00 PM – 5:15 PM Start your weekend on the water aboard Daniel Island Ferry's Friday Happy Hour Cruise. This relaxing 75-minute cruise...

Skye

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

description: Duration 3 Hours About Learn the secrets of Hilton Head’s history and the fascinating stories that bring it to life. This 3-hour expert guided tour takes you to five nearby historic sites in an air-conditioned bus. You will...

Five Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$755.00 - $1,075.00

description: Golf Cart Rentals! Duration 5 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

Corporate Parties & Team Building

Color Me Greenville

Book online
$50.00 - $400.00

duration: 1.5 Hours cancellation_summary: 7 Days meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: 1.5 hours active painting for groups of people. Includes a 11”x14” premium canvas for each attendant plus a 18”x24”...

???? Cook at Home Classic Lowcountry Boil

duration: 10 minutes meeting_point: 37 New Orleans Road Suite B, Hilton Head Island, SC pricing: * Base price: $59.99 for 2 people * Each additional person: $25.99 description: Our Lowcountry Boil bucket arrives packed with fresh, local ingredients...

Heritage Tour

Gullah Heritage Trail Tours

Book online
$25.00 - $49.00

description: *Gullah people are known for preserving more of their African linguistic and cultural heritage than any other African-American community in the United States.* ___________________________________ Duration 2.5 hours...

Kayak Rentals (Please call if unsure about booking a Guided Tour versus a Kayak Rental)

description: Kayak unguided if you have kayaking experience. We will go over the area with you, tell you about the dolphins favorite spots to hang out and answer any questions that a you have before departure. Of course our guided tours are...

One Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$21.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold...

3 Hour Private Spring Jocassee Boat Tour

description: Private 3hr Spring Tour on Beautiful Lake Jocassee! Rates - Private Charter (includes up to 6 people): $350 ***$50 for each additional person (up to 10 total passengers)*** About Boat Tour includes all major waterfalls...

Sunset Cruise

Island Time Charters

Book online
$350.00 - $450.00

The most spectacular views and vivid colors! Duration 2 or 3 Hours About This Sunset Cruise allows access to the best locations in the Low Country to enjoy the breathtaking views. With the sunset on one side of the boat and a view of the...

Dolphin Tour Aboard Dolphin Seafari
Book online
$10.00 - $750.00

duration: 1 hour 30 minutes cancellation_summary: Full refund if cancelled at least 48 hours before the tour; captain decides weather cancellations. group_size: Maximum 20 passengers accessibility: Handicapped accessible; guests should call...

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