Hilton Head, SC Vacations

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Featured Vacation Rentals

Sunset Rentals | Fazio 34

34 Fazio is a roomy, charmingly remodeled 4 bedroom, 3-bath, end unit townhouse in the handsome Palmetto Dunes Resort on Hilton Head Island.Upon entering this cavernous Palmetto Dunes villa you will be greeted by the tile floor entryway which leads...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Charming 3 bedroom 3 1/2 bath home in be...

Isle of PinesOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This striking three-bedroom three and a half bathroom home in the Sea Pines plantation is the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Family-Friendly Condo w/Free WiFi, Cover...

Summary:Centre Court 7832The Space:Elegance and convenience meet at this family-friendly condo near the beach! Centrecourt 7832 offers an open floor plan combining the kitchen, living room, and dining area, two huge bedroom suites, a huge covered...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Coastal condo with pool, tennis, and gym...

HH Beach & Tennis 158BOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say hello to the sunshine when you call this Hilton Head HH Beach & Tennis condo your...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Quaint One Bedroom Condominium Steps fro...

You'll appreciate this cozy one bedroom condominium located in Barrington Court within Palmetto Dunes Oceanfront Resort! Updates have newly been made to include all new stainless steel appliances, living room furnishings and linens in the primary...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
Waterfront Condo with Ocean Views, Share...

Close to fishing, horse riding, and more, this smoke-complimentary condo brings it all within reach. Palmetto Dunes Beach is just steps away while Palmetto Dunes Club is an painless 10-min. walk away. Spend a day at the close by beach, relax by the...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Hilton Head Farmer's Market

Coastal Discovery Museum Hilton Head

description: Rebuild our local food economy! _____________________ Description: Visit the Hilton Head Farmers Market at the Coastal Discovery Museum every Tuesday from 9:00am - 1:00pm. Take home fresh local produce, pasture raised chicken, free...

2-Hour Day Sail

BC2 - Island Head

Book online
$19.99 - $49.99

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Twelve Day Bike Rental

Wheelz of Hilton Head

Book online
$75.00 - $150.00

description: Twelve Day Bike Rental Rates Duration 12 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Kayak Rental: Club Pass Members

Island Head- Hilton Head Harbor

meeting_point: Hilton Head Harbor description: About Welcome to Hilton Head Island’s first Kayak Club! Imagine going for a paddle anytime you want hassle free– no buying, storing, or transporting – just hop in and go. Our kayak membership is...

HHI: Tales Through Time

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Learn about island history from an expert!* ___________________________________ Duration 1 Hour ___________________________________ About Hilton Head Island has been visited and inhabited for over 4,000 years—from the...

Shark Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $650.00

description: Shark fishing is an exhilarating and challenging endeavor that takes anglers on a thrilling journey! Duration 2 to 4 hours About As a captain, I've guided countless shark fishing trips, and each one brings its...

Hilton Head Full Moon Cruise

Island Head - Broad Creek

Book online
$59.99

description: Get on the water under a low country full moon! Duration 90 minutes About This is a one of a kind experience to see a full moon from the water. Enjoy a 90 minute slow cruise as you take in the beauty of the low country in a...

Fishing Charter - Kahuna

Native Son Adventures

Book online
$365.00 - $1,260.00

description: Duration 3 to 8 Hours About In-Shore and Near-Shore Fishing. The most stable adventure vessel on Hilton Head Island! The 26 foot Glacier Bay catamaran is the cream of the crop! He does it all, so let’s go have some fun...

Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: Day rental (24 Hours from the time of pick up) cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: *Perfect for your day exploring around Hilton Head!* Duration All day *All rentals must be...

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...

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

meeting_point: Hilton Head Island, SC description: Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to...

Private Sunset & Fireworks Cruise - 6p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

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