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
Lofted villa with private deck, streamin...

Summary:Sealoft 2055The Space:A lofted villa in a canopy of trees where the windows are the walls is waiting to welcome you to sun-soaked, oceanside, Lowcountry living! This unique, treehouse-like getaway offers a convenient location just a short...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
5 min walk to beach, ideal golf retreat,...

Summary:Greens 106The Space:Appreciate golf course vistas, beachy vibes, and a taste of the island lifestyle at this ideal condo just waiting for your next family vacation to Hilton Head. Step inside and you will immediately be greeted by the open...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Beautiful condo with furnished balcony, ...

Summary:HH Beach & Tennis A341The Space:Savor ample sunshine, sand, and surf for your upcoming hideaway to Hilton Head Island! This bright and breezy condo is part of the Hilton Head Island Beach & Tennis Resort, featuring a prime location near the...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
3 bedroom/3 bathroom 2nd floor Shipyard ...

HILTON HEAD ISLAND. Golfmaster is conveniently located in Shipyard Plantation. Overlooking the golf course these villas have a pool on-site.25 steps lead you to the entrance of this delightfully decorated villa. The modern kitchen comes completely...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
2-story house with private heated outdoo...

Summary:Mooring Buoy 151The Space:Mooring Buoy 151 is located in the handsome Palmetto Dunes plantation. The moment you walk through the double wooden doors into the two-story Great Room, you feel that you have entered into a bright and great...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Three Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$45.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** These strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Ohana Sunset Dolphin Cruise
Book online
$45.00 - $2,500.00

meeting_point: Hilton Head, SC description: Explore the marsh and enjoy the view of the incredible Lowcountry sunset! --- Join us for this 90-minute tour to learn about the salt marsh and search for local dolphins aboard the luxury catamaran...

Lowcountry Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

duration: 10–15 minutes cancellation_summary: Full refund if weather forces cancellation and no mutually available reschedule; otherwise weather-dependent rescheduling. meeting_point: Jarvis Creek Park, 100 Jarvis Park Rd, Hilton Head Island...

Two Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

description: Enjoy miles and miles of scenic bike paths Duration 2 Days 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...

Two Day Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$69.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Rate Two Day Rental: $69.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 2 Days

Weekend 10:30am-6:15pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekend 10:30 am to 6:15 pm- Golf Cart Rental *Must have valid Driver's License to rent a cart.*

Sunset & Fireworks Tour

duration: 2.5 hours cancellation_summary: All reservations are subject to our 48 hour cancellation policy! group_size: Up to 12 people description: Experience the Magic of Summer Nights! Every Tuesday, Harbour Fest lights up the sky -- and there's...

Discovery Lab Open House

Coastal Discovery Museum Hilton Head

description: Rates Suggested $5 donation per person (Ages 4+). Children must be accompanied by an adult. Everyone must have fun!! Duration Drop in any time during Open House hours and stay as long as you'd like! Discovery Lab During the...

Pirate Cruise

Pirates HHI

Book online
$10.00 - $39.99

duration: 1.5 Hours cancellation_summary: Full Refunds are issued with 48 hours advanced notice meeting_point: 86 Helmsman Way, Hilton Head, SC 29928 - Check In at the Lowcountry Watersports Office to the left of Black Marlin Restaurant pricing...

Sundance DX20

Timberlake Marina

Book online
$300.00 - $900.00

duration: 8.5 Hours min_age: 23 group_size: Maximum capacity is 8 people or 1,160 lbs. description: Do it All Boat: fishing, cruising and family use Fishing-first, family-friendly utility boat Yamaha 115, Capacity 8, 1160 lb There’s nothing quite...

Hidden Treasures Tour

Hidden Treasures Bluffton

Book online
$20.00 - $500.00

description: Come and discover the Hidden, but not Forgotten Treasures of Historic Bluffton. Duration 45 Minutes About We will discover long lost Hidden Treasures in and around Beautiful Old Town Bluffton. More info There is a 4 person...

Bunny Eggspress      (28 March & 4 April)

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held the two Saturdays before Easter each year. Riders will board the train for a 3-mile trip to the event area. We will stop the train...

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