Hilton Head, SC Vacations

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Featured Vacation Rentals

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
Beautiful Beachside Villa! Oceanfront Po...

Welcome to Ocean Dunes 102!This striking first-floor condo offers a fresh and modern getaway, newly repainted and refreshed for your comfort. Featuring one bedroom and one bath, the villa features a new king-sized bed in the master bedroom and a new...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Hilton Head Spinnaker-Shipyard Plantatio...

Spinnaker at Shipyard, 2 story townhouse, deck overlooks lagoon and golf course, includes 2 bicycles, complimentary golf and tennis each day for 2, handsome outdoor pool with grilles and play areas.Gated community with miles of bicycle trails, ...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Hilton Head Stay | Beach, Pool + Full Ki...

The Village at Palmetto Dunes offers a casual Hilton Head stay just steps from the beach, with painless access to golf, tennis, pickleball, and breathtaking bicycle paths. Located within Palmetto Dunes Resort, this property places you close to...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Large Sprawling Home Very Close to the B...

This sizable six bedroom and seven bathroom home has everything you'll need to provide a ideal vacation for your whole family! All furnishings in the entire home has been replaced and there are too many updates to name!The sprawling chef-style...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 12
Family-Friendly Condo with Shared Pool &...

Summary:Queens Grant 768The Space:Appreciate the best of Hilton Head Island living at this inviting Queens Grant villa, where calming days by the shared pool, breathtaking bicycle rides through the plantation, and friendly matches on the on-site...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Creek Cat Tour

Lowcountry Watersports

Book online
$120.00 - $145.00

duration: 2 Hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 group_size: 2 people per creek...

2 Hour Lane Rental

Palmetto Axes

Book online
$45.00

description: Hit the Bullseye! Duration 2 Hours About Enjoy hurling axes as your friends or family marvel in your skills. Team up to see who the best pair is or compete individually in a winner take all (the glory and bragging rights...

12 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$48.00 - $335.00

duration: 12 Days cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After...

Riverside Lounge

Vintage View River Retreat

Book online
$5.00 - $125.00

duration: 5 Hours description: Our new Riverside Lounges take the traditional park picnic experience and elevate it to a premium, private basecamp on the banks of the Pacolet River. Each lounge is thoughtfully designed to provide a comfortable and...

Cinco de Mayo…..The YoCo LoCo way!

description: About Hop aboard for a fiesta on wheels! We will kick this tour off at The Print Shop, Fort Mill. Enjoy great beer and beautiful outdoor seating. We will cruise over to Tony’s Cantina in Riverwalk to enjoy margaritas and delicious...

Kids Summer Splatter-Paint Camps

Color Me Greenville

Book online
$225.00

duration: 30 mins meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: Kids Summer Splatter-Paint Camps

Private Sunrise Cruise

Island Head - Broad Creek

Book online
$325.00

duration: 1.5 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 14 Passengers pricing: *All Ages, Up to 14...

Paint the Pony - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

Private Kayak Date Tour

Crooked Creek Kayaks

Book online
$175.00

duration: 2 Hours group_size: Maximum 2 people description: Enjoy exclusive, private guided access into Jarvis Creek’s quiet, winding estuarine waterways — reserved solely for your group and led by your own personal guide. This tailored...

3 Hour Evening Shark Trip

Black & Blue Charters

Book online
$625.00

description: *3 Hour Evening Shark Trip* Duration 3 Hours About Evening shark fishing in calm waters. Great trip for kids.

Lowcountry Seafood Experience

May River Excursions

Book online
$135.00

meeting_point: Hudson's Seafood Restaurant description: Rate - $135 per person includes boat excursion as well as a meal and one beverage __________ Duration - 2 Hour Boat Excursion with meal afterwards at Hudson's ____________ About ...

Private Boat Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$225.00 - $350.00

duration: 1.75 - 4 Hours cancellation_summary: 48 hours - No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Up to 8 recommend. If more please call. accessibility: Boats take 2 steps from...

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