Hilton Head, SC Vacations

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Featured Vacation Rentals

Beautiful, Easy Ocean Access

2 BR townhouse condo. Delightfully furnished, 1 1/2 baths, full kitchen, DR and deck overlooking striking, partially shaded pool. Across street from the beach with walk through access. Complex provides new gas poolside grilles for calming meals...

  • Hilton Head
  • 2 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, impressive outdoor pool with grilles and play areas.Gated community with miles of bicycle trails, ...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Welcome to Eleventh Heaven!

This beautiful two-bedroom, two-bath villa in Hilton Head Island features amazing vistas of the Eleventh Hole on the George Fazio Golf Course. The villa has coastal artwork and decor throughout. The comfortable and inviting living room has a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
32 Corine, Pickleball, Seasonal Beach Sh...

32 Corrine Lane is a gorgeously decorated 6-bedroom, 6-bath open concept home that is really a extravagant getaway for families or enormous groups. The presence of three primary king bedroom suites, private balconies and a private pool ensure that...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 15
Centrally located condo with pool, tenni...

Cordillo by the SeaOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Snowbird special 15% off for stays over 28 days now through February Located in the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Private pool - space for the whole famil...

This bright and roomy home, located on a peaceful cul-de-sac, has everything you will need to savor your next family adventure on Hilton Head!The pretty LIVING ROOM greets you as you enter through a two-story entry. With classy and comfortable...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Full Moon Float

Vintage View River Retreat

Book online
$15.00 - $45.00

duration: Hourly meeting_point: 250 Phifer Line Rd, Spartanburg SC 29307 description: Full Moon Float with Vintage View Adventures is pure moonlit magic on the Pacolet River! Join us for a twilight paddle as the sun sets and the full moon rises...

Seafood Fest Family Fishing

Hilton Head Island Recreation Association

Book online
$25.00

duration: 2 Hours meeting_point: Rowing and Sailing Center group_size: Up to 20 Groups description: Enjoy a night of fishing and education with your family and learn some pro tips from seasoned Lowcountry fishermen! In this 2 hour event, a featured...

Dolphin Excursion

May River Excursions

Book online
$40.00 - $50.00

*Experience the Atlantic Bottle-nose Dolphin up close and personal in their natural habit!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ ...

3 Hour Private Spring Jocassee Boat Tour

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, Limited swim time...

PB Private SUP Instruction
Book online
$75.00 - $325.00

*Get on the water with one of our custom kayak tours & classes* Outside Palmetto Bluff has a professional staff of Instructors ready to help you enjoy the fun, fitness and beauty of the fastest growing watersport in the world! All lessons...

Labor Day Sale

The Pixel Experience

Book online
$20.00

Greenville's First Premier Selfie Museum Duration 1 Hour Session About The Pixel Experience is a selfie museum with fun and interactive installation pieces. Through this space, guests can tour over 20 instagrammable backdrops where you can...

Shrimping

May River Excursions

Book online
$300.00 - $400.00

*Experience sea life like never before!* ___________________________________ **Please note**: Shrimping is only available from August-December ___________________________________ Rates **Private Charter** - $300 2 hours (for 6 people and...

1 Hour Dolphin Tour

H2O Sports

Book online
$25.00 - $350.00

duration: 1 hour tour cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Shark Tooth Treasure Bag

Lowcountry Watersports

Book online
$9.99

Private Morning Sail and Dolphin watch on Knot The Office
Book online
$315.00 - $395.00

duration: 2 hours meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 passengers description: Mornings are an ideal time to experience nature’s most playful wildlife. We’ll motor from the dock to...

Daufuskie Island History & Artisans Excursion

*Catch a glimpse into Lowcountry history!* --- Description This 4.5-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of the island. Visit several one-of-a-kind places...

Backwater Adventure Day

May River Excursions

Book online
$525.00 - $825.00

About - Take a private custom excursion through the backwater ways and marshes around the barrier islands of the Lowcountry with a local captain. Choose from inshore fishing, hand lining for crabs, shrimping, shelling or shark tooth hunting...

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