Hilton Head, SC Vacations

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Featured Vacation Rentals

Quiet Hilton Head Getaway with WiFi, Poo...

Summary:Island Club 1404The Space:This two-bedroom, two-bath Island Club condo is the right one to choose for family getaways and other gatherings. Fun can be had by all at the community’s pool complex, hot tub, nine tennis courts, fishing lagoon...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
1st floor condo with pool, tennis, patio...

Summary:Spa On Port Royal Sound 3136The Space:Feel the ultimate beach hideaway at this gorgeous first-floor condo in Hilton Head, SC. Just a 5-min. walk to the beach, this comfortable getaway offers a screened-in patio where you can relax and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Completely Updated Two Bedroom Villa wit...

This impressive two bedroom Queens Grant villa has been completely refreshed! With its single-level, wide open floor plan, you're going to be glad you chose this fantastic villa.The kitchen has been completely updated with quartz countertops...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Pet friendly centrally located villa in ...

Feel the best of Hilton Head Island from this gorgeously located 2-bedroom, 2-bath villa in the heart of Harbour Town within the world-acclaimed Sea Pines Resort.Leave the car behind and appreciate one of the most walkable locations on the island...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3 Bed/3 Bath Villa on the Fourth Floor w...

Discover the beauty of Hilton Head Island with striking ocean and beach vistas from the private balcony of one of our oceanfront villas. Choose from cavernous 1, 2, or 3-bedroom villas in a variety of floor plans, each offering a comfortable...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Charming bay view villa with pool, washe...

Summary:Harbourside 7126The Space:There's something here for everybody at this splendid villa! If you're a fan of music, you'll be glad to know that The Jazz Corner is right around the corner—less than three miles out! Savor a alluring walk on the...

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

Hilton Head Tours & Activities

Pirate Cruise

Pirates HHI

Book online
$10.00 - $39.99

duration: 1.5 Hours cancellation_summary: Full Refunds are issued with 48 hours advanced notice meeting_point: 86 Helmsman Way, Hilton Head, SC 29928 - Check In at the Lowcountry Watersports Office to the left of Black Marlin Restaurant pricing...

Cocktails & Camellias

Coastal Discovery Museum Hilton Head

Book online
$200.00

duration: 3 hours meeting_point: 70 Honey Horn Dr, Hilton Head Island, SC min_age: 21 accessibility: Wheelchair accessible description: Immerse yourself in the beauty of the Lowcountry at *Cocktails & Camellias*, an elegant evening set against the...

Glow in the Dark Splatter Party! - Basic
Book online
$45.00 - $550.00

duration: 1.5 hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max description: It’s your invite to light up the night and vibe out with your crew! Experience the thrill of our glow-in-the-dark parties...

Afternoon Wambaw Creek Wilderness Area Tour - 2 Hour
Book online
$52.00 - $104.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Shark Fishing Charter

Gone Fishing HHI

Book online
$400.00 - $700.00

description: Fish like a local! Duration & Rates **2 Hour Charter** - *$375* **3 Hour Charter** - *$475* **4 Hour Charter** - *$575* About The two hour trip is great for groups with young kids, beginners, or groups just looking to get out for...

Three Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$485.00 - $740.00

description: Golf Cart Rentals! Duration 3 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...

Guided Congaree National Park Kayak Tour

meeting_point: The Congaree National Park description: *Guided Congaree National Park Kayak Tour* _____________ Rates **Floating Options** * Single Kayak * Tandem Kayak **Adult (Ages 13+):** $80 **Children (Ages 12 & under):*...

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

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...

Memberships

Coastal Discovery Museum

Book online
$100.00 - $1,000.00

description: All Members Receive Invitations to members-only seasonal programs Invitations to exhibit openings Advanced notice of upcoming events and lectures Monthly membership bulletin Discounts in the Museum Store $100 Supporting...

Four Day Electric Bike Rental
Book online
$200.00

duration: 4 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...

Private Lesson with Dustin Hayes

Palmetto Dunes Golf Academy

Book online
$90.00

description: About Dustin Hayes - Dustin has a friendly and fun personality - Trained by the award-winning Palmetto Dunes Golf Academy Staff - Excellent with juniors and adults - Ohio All State Champion About the Palmetto Dunes Golf...

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