Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Sunny & peaceful resort with golf, pool,...

Summary:Golfmaster 206The Space:This striking and modern multi-level Golfmaster condo is an ideal home base for appreciating the best of Hilton Head—whether you’re here for golf, the beach, or great local dining.Take advantage of resort-style...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Coastal Villa with Spacious Deck, Pool &...

Summary:Beachwalk 129The Space:129 Beachwalk is a single-story villa in Shipyard Plantation, directly across from the complex pool and a few mins.' walk to the beach. The gated deck is the ideal spot for outdoor dining, located through sliding doors...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beachfront beauty with pool access firep...

Summary:Sea PointeThe Space:This chic five-bedroom home is just steps away from Singleton Beach and the shared community pool! Bring the whole family and create sun-soaked, lifelong memories in Hilton Head. When your toes aren't dug into the warm...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Charming, family friendly condo with pri...

Summary:Turnberry Village 251The Space:Sunkissed skin and salty air await you at this Hilton Head Island getaway. Sporting a full kitchen with modern appliances, a enormous living area with a flat-screen TV, and a private deck surrounded by...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Large Three Bedroom Villa on George Fazi...

You're going to appreciate this enormous three bedroom villa on George Fazio Golf Course. There'll be ample space for the whole family!The kitchen is giant with tons of space for storing groceries. The appliances are all stainless steel and...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Spacious Villa waterview haven with deck...

Summary:Sound Villas 1452The Space:A roomy haven in the Sound Villas community, this family friendly home is a sure bet for a vacation no matter the time of year! The sprawling three story floor plan features ample room to relax and entertain both...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15

Hilton Head Tours & Activities

Super SUP Rentals

Saluda Lake Landing

Book online
$60.00 - $200.00

duration: 2 hrs, 4 hrs, or Full Day cancellation_summary: Cancellations made 48 hours or less before your rental time are non-refundable. We appreciate your understanding and look forward to seeing you on the water! meeting_point: 605 Motor Boat...

Three Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$480.00

description: Duration 3 Hours ___________________________________ About Catch sharks, other species, might catch some nice fish and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you...

Italian Club - Private Sunset Dinner Cruise

duration: 2 Hours meeting_point: Hilton Head Island min_age: 13 description: Hilton Head Italian Club - Sunset Dinner Cruise! **Book online now for fastest and most convenient check out.** *Departing from Harbour Town!* Duration 2...

AYA Bandana

Historic Mitchelville Freedom Park

Book online
$10.00

pricing: $10 description: AYA Bandana

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

description: Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy...

Five Hour Inshore/Nearshore Fishing Trip

Hilton Head Island Tours

Book online
$645.00 - $695.00

description: *Five Hour Inshore/Nearshore Fishing Trip* ___________________________________ Rates **Up to Four Guests** - $645.00 **Five Guests** - $675.00 **Six Guests** - $695.00 ***All ages welcome! | Maximum of 1200...

Camellia Talk & Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $25.00

description: Camellias are fascinating plants with a rich history. While they are not native to the American continent, they have been part of the southern landscape since the 1700s. Come and learn about the history, diversity, and significance of...

One Week Electric Bike Rental
Book online
$250.00

duration: 7 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Crabbing

May River Excursions

Book online
$300.00

description: *Our most interactive and famous excursion!* ___________________________________ Rates **Private Charter** - $300 for 6 people or less. *(Can hold up to 12 people for extra charge, call for more...

Night Games

Red Oak Airsoft & Paintball

Book online
$25.00 - $45.00

duration: 5 Hours cancellation_summary: 48 Hours min_age: 12 description: Come join us for another Night Games installment. We will begin check in at 6 and the games start at 7. If you need rental equipment (additional $20) please select that option...

PB Palmetto Bluff Pedego Bike Tour

meeting_point: Palmetto Bluff, Bluffton description: About There is no better way to discover Palmetto Bluff than on a comfortable seat of a Pedego electric bike. Pedego electric bikes allow riders to travel farther and faster, and breeze through...

Morning Half Day Sail Trip On Seas the Moment - Our Newest boat
Book online
$1,144.60 - $1,450.00

duration: 4 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we...

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