Hilton Head, SC Vacations

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Featured Vacation Rentals

2nd floor Coastal Condo, pool, tennis an...

Summary:Spa On Port Royal Sound 3227The Space:Located in the serene coastal setting of Hilton Head, SC, this delightfully decorated condo has been newly modernized and thoughtfully upgraded to offer a fresh, modern ambiance for your next vacation...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious, Renovated House with Private S...

Summary:Ocean EscapeThe Space:*Please read our important pool heat information to help you have the best vacation possible!*This property has a pool and spa that can be heated between Labor Day and Memorial Day for an additional fee of...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Scenic Golf Front Condo with Large Deck,...

Summary:Water Oak 27The Space:Welcome to your ideal hideaway in Hilton Head, SC! This appealing condo is located within the gated community of Palmetto Dunes Oceanfront Resort, offering both privacy and convenience. This refreshed condo offers...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Exquisite oceanfront top-floor condo has...

Summary:Island Club 5503The Space:Feel spectacular unobstructed ocean vistas, morning sunrises, and gorgeous beach vistas from the moment you enter the front door, all the way through the living room to the top floor balcony. Savor luxury vinyl...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Pet friendly condo on golf course, near ...

Summary:Shipmaster 703The Space:Welcome to your ideal hideaway in Hilton Head, SC! This appealing condo, located in the esteemed Shipyard Plantation, offers a ideal blend of relaxation and adventure. You can relax on the outdoor patio equipped with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Top floor Fiddlers Cove condo with resor...

Summary:Fiddlers Cove 2KThe Space:Appreciate a coveted top floor location, set amid the delightfully maintained grounds of Fiddler’s Cove. This gated community features a plethora of top notch amenities, including multiple pools, a hot tub...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Bunch Bike - Family E-Bike Fun!

Pedego Electric Bikes Greenville

Book online
$109.00

duration: 6 to 8 Hours meeting_point: Pedego Electric Bikes Greenville. Located at Hampton Station - 1320 Hampton Ave Ext. STE 11A Greenville, SC 29601 description: Experience family fun like never before! ???? Experience the Thrill of...

Private Lesson with Jason Heintenchel

Palmetto Dunes Golf Academy

Book online
$90.00

meeting_point: Arthur Hills Golf Course description: About the Palmetto Dunes Golf Academy The Palmetto Dunes Golf Academy in Hilton Head, South Carolina, is one of the most respected golf schools in the world. Featuring lessons, clinics and...

Four Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$645.00 - $935.00

description: Golf Cart Rentals! Duration 4 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

Pony Rides - 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: Let your little ones experience the joy of horseback riding with our...

SC Pimento Cheese Festival - Tasting Ticket

meeting_point: Saluda Shoals- 6071 St Andrews Road, Columbia, SC 29212 description: A festival to showcase South Carolina's Favorite snack, Pimento Cheese Rates General Admission is Free and $5 Parking Fee per car at Gate Tasting Tickets are...

11 Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$86.46 - $205.81

description: Enjoy miles and miles of scenic bike paths Duration 11 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...

A Taste of Daufuskie Island
Book online
$595.00 - $1,175.00

duration: 4 meeting_point: 1 Shelter Cove Lane, Hilton Head SC 29928 group_size: up to 6 pricing: $595/up to 6 guests description: Embark on an unforgettable Lowcountry adventure as you journey through the Carolina saltmarsh ecoststem to the...

Parasailing

Island Head- Hilton Head Harbor

Book online
$29.99 - $999.00

meeting_point: Hilton Head Harbor description: *High Flying Family-Fun Parasail over Hilton Head.* ___________________________________ Rates **Flyer (Ages 6+):** $95 **Observer (All Ages):** $49 ___________________________________ ...

Art Market: Fine Art and Craft Festival Tickets

Coastal Discovery Museum Hilton Head

Book online
$5.00

meeting_point: Coastal Discovery Museum at Honey Horn description: $5 per adult, FREE for ages 12 and under Original art for sale Food and drink available for purchase Advance tickets are not required, but only cash will be accepted for...

PB PVT Bluffton Beach Kayak Adventure

About Paddle to one of the Lowcountry's most celebrated hidden gems on this private, unique May River adventure. Departing from Wilson Landing, you'll enjoy a leisurely guided kayak journey through the scenic salt marshes of Palmetto Bluff en...

Old Town Bluffton

Hilton Head Helicopter Tours

Book online
$229.00

max_age: 100 description: Experience an exhilarating helicopter tour over Hilton Head and Bluffton that highlights the area's natural beauty and historic sites. Fly over Pinckney Island to look for bald eagles and hawks, sweep across Bluffton’s...

PB Private Biking the Bluff
Book online
$75.00 - $265.00

meeting_point: Palmetto Bluff

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