Hilton Head, SC Vacations

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Featured Vacation Rentals

Beautiful villa, family friendly with ba...

Summary:Tanglewood 1006The Space:Welcome to Hilton Head Island, the crown jewel of the coast of South Carolina. Not only are there spectacular vistas and white shores that await you, there are no shortages of things to do during your stay. Take a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stunningly remodeled 3rd floor villa wit...

Summary:Villamare 3329The Space:3329 Villamare is an amazingly modernized 2 bedroom, 2 bathroom condo with fantastic ocean vistas. The open floor plan contains deluxe furnishings, modren coastal decor and an added office space with an executive...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Family-Friendly Oasis. Beautifully Lands...

Welcome to Hilton Head Beach Villa 27!! Oceanview Villa with Pool Access and Family-Friendly Conveniences!Exciting News: Our Charming New Swimming Pool is Now Open!This villa offers a prime oceanview location and direct access to a striking...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Heated Oceanfront Pool with Hot Tub! Clo...

Welcome to your ideal hideaway! This attractively decorated, roomy two-bedroom, two-bath flat-style condo offers striking resort vistas and a calming, modren ambiance. Inside, you'll find a comfortable living and dining area, a entirely equipped...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Coastal condo on the beach w/ panoramic ...

Hampton Place 5501Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering delightful vistas of the coast from the private balcony, this newly remodeled villa...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 2
Peaceful villa with large deck and lagoo...

Calibogue Club 2617Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the serene surroundings of Hilton Head, SC, this striking villa offers calming...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

One Hour Rental (Walk Up)

South Beach Bike Rentals

Book online
$20.00 - $49.00

description: Enjoy miles and miles of scenic bike paths Duration 1 hour About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

Cruise Through The Stars

Vagabond Cruise

Book online
$19.95 - $39.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Stroller and wheelchair accessible on the lower deck of the Vagabond description: ![Description of...

2 Hour Beachcombing Dolphin Tour
Book online
$15.00 - $650.00

duration: 2 hour tour cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Beach Discovery Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Join a museum naturalist on an amazing nature tour!* ___________________________________ Duration 1.5 Hours ___________________________________ About Ever wonder who makes those holes in the sand—or when and why sea turtles...

Sun Care Kit by Aloe Up

Lowcountry Watersports

Book online
$15.99

SC Pimento Cheese Festival Merch
Book online
$2.00 - $18.00

Private Water Ski Adventure Day (7-12 Passengers)

Island Head- Hilton Head Harbor

Book online
$450.00 - $1,350.00

description: Come enjoy a day on the water with Island Head! About Come enjoy a day on the water with Island Head! This private experience includes a USCG captain to drive the boat and assist in the water sport of your choice. A tube, water skis...

Kayak Tour of Jarvis Creek

Coastal Discovery Museum Hilton Head

Book online
$36.00 - $40.00

meeting_point: Jarvis Creek Water Sports description: *Look for for bottle-nosed dolphins, wading birds and other local wildlife!* ___________________________________ Duration 2 Hours (including safety training and...

Private Lesson with George Spinella

Palmetto Dunes Golf Academy

Book online
$90.00

meeting_point: Arthur Hills Golf Course description: About George Spinella George Spinella graduated from Siena College in 2003 and the San Diego Golf Academy in 2005. He is the 1st Assistant at the George Fazio Course and has been teaching with...

Old T-Shirt

Historic Mitchelville Freedom Park

Book online
$5.00

pricing: $5 description: Old T-Shirt

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...

Twilight Guided Ghost Story Tour

Mungeon Creek Golf Cart Rental

Book online
$61.32 - $235.85

duration: 2 Hours group_size: Up to 20 guests description: Ride into the haunted history of Daufuskie Island with our Twilight Guided Ghost Story Tour! Join us for a chilling 2-hour adventure as the sun sets and shadows creep across the island. Your...

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