Hilton Head, SC Vacations

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Featured Vacation Rentals

Dreamy island villa with pool, balcony, ...

Treetops 4904Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you are trying to get a taste of the bright, beachy lifestyle of Hilton Head Island, look no...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
60 Lawton Road, Sea Pines

Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here's the skinny - just buzz us for more details: Our advertised prices are our very best rates and calendar shows real time availability. We encourage you to book online!• Gorgeously...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
HHI Beach Cozy Condo: Pool, Gym & Tennis

Hilton Head Island Beach & Tennis Resort | Folly Field Beach Park On-SiteLocated in a resort community, just steps from the sugar-white sands along the Atlantic shoreline, this Hilton Head Island vacation rental offers countless beachfront fun. Cool...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Stunning, family-friendly condo w/shared...

Harbourside 7150Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Have the vacation of a lifetime staying in this rare, top-level, end-unit with a wrap-around...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Large Home with Spectacular Panoramic Vi...

You're going to appreciate this enormous home with spectacular expansive vistas of Robert Trent Jones Golf Course and the 11 Mile Lagoon! From when you first pull up to the home you'll notice it's very private with a modest fenced-in garden in the...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
4 Collier Ct, Oceanview, Pool, Elevator,...
4.5
(2)

4 Collier Court, Hilton Head Island is a property that is boasting fresh paint and décor enhancements updates, this home is a true gem. Just 50 feet from the beach path, it offers beautiful vistas of the ocean and marsh. With 6 bedrooms, 6.5...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14

Hilton Head Tours & Activities

22' Hurricane Fun Deck

Hilton Head Island Boat Rentals

Book online
$325.00 - $1,525.00

meeting_point: 1 Shelter Cove Lane, Hilton Head Island, SC 29928 description: About 22' Hurricane Deck Boat The Hurricane Deck Boat's "Fun Deck" Layout Up to 6 people Max Duration 2-8 Hours

Beachcombing & Eco Tour (2 Hrs)

Beaufort Dolphin Adventures

Book online
$372.64

duration: 2 Hours cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances...

Tubing and Dolphin - 6 max

meeting_point: Hilton Head Island, SC description: Family Fun With Nature, Tubing and Exploring! --- Join us for a boating and tubing tour through the Lowcountry waters! Watch for birds and dolphin through the salt marsh ecosystem and get behind...

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...

Fireworks Paddle
Book online
$55.00 - $125.00

description: *Few experiences are more memorable than watching fireworks from the seat of a kayak.* --- > Rates >- **Adults Single Kayak:** $55 >- **Adult & Child Double Kayak:** $90 >- **Two Adult Double Kayak:** $110 --- ...

Private Day Sail

BC2 - Island Head

Book online
$900.00 - $2,500.00

duration: 2-6 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Santa’s Twilight Express

The South Carolina Railroad Museum

Book online
$27.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual twilight holiday ride. Santa walks through the train and comes to you—no lines! As we travel down the tracks, the...

SCM WAHHI Outback Page Island

description: *Boating and kayaking in pristine salt marshes!* --- Description One of our signature programs and an exceptional value from Outside! The Outback begins with a guided boat trip where the captain shares stories of the Lowcountry...

Historic River Excursion

May River Excursions

Book online
$40.00 - $50.00

description: *Learn more about Bluffton through our scenic trip!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ Duration 1.5...

Bar Crawl

Flip Flop Charters

Book online
$625.00 - $750.00

Beautiful Scenery Duration - 3 hours - 4 hours About If you’re looking for some adult fun, there is no shortage of waterfront bars in our area. We’d love to take you to some of our favorites or let you pick the itinerary.. some of our...

3 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$21.00 - $140.00

duration: 3 Days cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours...

Two Week Bike Rental

Wheelz of Hilton Head

Book online
$85.00 - $170.00

description: Two Week Bike Rental Rates Duration 14 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...

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