Hilton Head, SC Vacations

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Featured Vacation Rentals

Top floor vacation rental - expansive oc...

Handsome ocean vistas are just one of the marvelous benefits to savor from this top floor Hilton Head Island, SC rental. Savor broad ocean vistas and you are just steps away from the beach. Sliding door opens to the balcony with ocean view. Kitchen...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Beautiful half acre estate home with pri...

Summary:Magnolia Crescent 3The Space:Boasting over 3,100 square feet of sunlit living space, this half-acre 4BR/4BA estate presents the ideal group hideaway - complete with complimentary passes to the Harbour Town Pool. Delightfully refreshed...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Near Shipyard Beach | Pool, Bikes + Full...

Southwind II at Shipyard puts you in the kind of Hilton Head setting people hope to find, where golf and nature vistas replace busy roads. Shipyard Beach is about 0.8 miles away, and Coligny Beach Park is roughly 2.5 miles out for dining, shopping...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Waterfront, dog-friendly Villa at Shelte...

Summary:Harbourside 7127The Space:Spectacular vistas of the water fill nearly every window at this two-story villa, enviably located right alongside Shelter Cove Harbor and Marina. In this breathtaking waterfront setting, you'll have unbeatable...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
9 Singleton Beach, Ensuites in Every Bed...

9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring vistas! Ideal for multiple families, this impressive seven-bedroom, five-and-a-half-bathroom home spans three stories with an elevator. Professionally...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
1 bedroom top floor Seaside Villa with s...

This enchanting villa features a private bedroom with a queen-size bed and a entirely equipped kitchen. The open-concept living and dining area provides a comfortable space for relaxation and meals. Additional sleeping arrangements include a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Paint the Pony - Montage Guests
Book online
$170.00

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 Inshore Charter Fishing aboard Hobo

duration: 3 hours cancellation_summary: 48 hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way. Please proceed down to the first dosk on the right side of the marina. group_size: Licensed for up to 16 passengers; rate includes 6...

Beach Gear Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $75.00

description: Everything you need for a fun and comfortable day at the beach! Duration 24 Hours About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later...

Ten Day Electric Bike Rental
Book online
$400.00

duration: 10 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...

New Exhibition: Opening Reception

Coastal Discovery Museum Hilton Head

duration: 5:00PM - 7:00PM description: The Coastal Discovery Museum, a Smithsonian Affiliate, opens a retrospective exhibition, “It's Thursday! Artists of the Round Table,” on November 12, celebrating 15 prominent local artists who gathered...

Private Sunset Cruise (Up to 14 Passengers)

Island Head- Hilton Head Harbor

Book online
$549.00 - $699.00

meeting_point: 43 Jenkins Rd, Hilton Head, 29926, South Carolina description: The private sunset cruise is the perfect way to end a day on Hilton Head Island. There is nothing quite like a low country sunset, especially seeing one from the water...

Pride on the Pacolet

Vintage View River Retreat

Book online
$20.00 - $45.00

duration: 3 Hours description: Come celebrate Pride Month and light up your weekend! Glide down the river with glowing rainbow gear, good vibes, and nonstop Saturday night fun. This 3 hour adventure lets you float while the sun goes down, laugh with...

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...

Sunset Guided Kayak Tour

Island Head- Hilton Head Harbor

Book online
$49.00 - $95.00

description: *Paddle the Low Country!* ___________________________________ Rates **Kayak:** $49 **Tandem Kayak:** $95 *All Ages* ___________________________________ Duration 1 hour and 30 minutes ___________________________________ ...

Sunset Dolphin Cruise
Book online
$45.00 - $55.00

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane pricing: $45 for children 12 and younger $55 for 13 and over description: Looking for a memorable evening on the water? Our Sunset Dolphin Cruise in Hilton Head...

Five Day Bike Rental

Wheelz of Hilton Head

Book online
$46.00 - $92.00

description: Five Day Bike Rental Rates Duration 5 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Four Hour Inshore Shark Fishing Trip

Hilton Head Island Tours

Book online
$525.00 - $565.00

description: *4hr Shark Fishing Trip in Calm Coastal Waters* ___________________________________ Rates **Up to Four Guests** - $525.00 **Five Guests** - $545.00 **Six Guests** - $565.00 ***All ages welcome! | Maximum of 1200...

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