Hilton Head, SC Vacations

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Featured Vacation Rentals

Sunset Rentals | St. Andrews 1772 | Dog ...

This 2 bedroom, 2 Bath in St. Andrews Commons is a opulent hideaway in the middle of the handsome Palmetto Dunes plantation. The entry opens to a long platform area that overlooks the sunken living room, cathedral ceiling throughout the kitchen and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious house by the beach with screene...

Salt Air SanctuaryOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just a fast walk down the street to Driessen Beach Park, this striking home in Hilton Head...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Dog-friendly home in Sea Pines with priv...

Planters Wood 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel a true taste of the Lowcountry at this fantastic Hilton Head Island hideaway. Located in...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Snowbird-friendly home with 2 decks, enc...

Hammock Breeze 21Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideally located on the spectacular north side of Hilton Head Island, this charming home is...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
2 Bedroom and 2 Bath Condo unit in Ocean...

The Island:Hilton Head Island may only be 12 miles by 5 miles wide, but you’ll find everything you need here for the ultimate Island getaway. Appreciate days basking in the sun on some of the best beaches in the country. Get into the swing of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Marriott's Barony Beach - Many Weeks Ava...

***Please use the "Contact Host" located under Check Availability for any reservation questions that you may have.Most high-demand season weeks are offered on a Friday, Saturday, and Sunday check-in & out with SEVEN NIGHT INCREMENTS. HOWEVER, we may...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

One Week - 4 Passenger Quad Stroller Wagon with Removable Canopy

PERFECT CARRIER FOR KIDS – Baby bags. Booster seats. Strollers. Sometimes, taking our little ones on the go with us is nearly impossible! Babies and toddlers alike love strolling around in the WONDERFOLD X4 Wagon, secured in a 5-point harness and...

Beachcombing & Eco Tour (3 Hrs)

Beaufort Dolphin Adventures

Book online
$448.11

duration: 3 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...

Gift Card

Anchors Away Sailing Charters

Purchase a gift card for a friend!

Flyboard 20 Minute

Carolina Hydrofly

Book online
$99.00

20 Minute Flyboard Pro Series Experience What's Included? 15 Min Flight Time. Includes 10 minutes of instruction time, fuel, life jacket, wetsuit, and helmet We advise everyone to arrive at least 30 minutes before your start time. If...

Lighthouse Tour

Hilton Head Helicopter Tours

Book online
$369.00

Come see this magnificent fort, beaches and property from the air! Duration - **40 minutes** About - Along the way you will see old lighthouses, breath-taking coastal views of the Low Country, and small remote islands only few have ever...

Private Charter (Up to 14 Passengers)

Island Head - Broad Creek

Book online
$229.00 - $1,603.00

duration: 1 - 8 Hour Options cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 14 Passengers description: Enjoy a...

DIY Custom Sneaker Painting

Color Me Greenville

Book online
$45.00

duration: 3 Hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: Hey there, Sneakerheads and sneaker enthusiasts! Ready to craft your own sole-ful masterpiece? Let your imagination run wild as our team helps you design a...

4.5 Hour Deep Sea Fishing Aboard the Drifter
Book online
$65.00 - $1,000.00

*Fishing for the whole family on Hilton Head Island!* ___________________________________ Rates - **4.5 Hour Deep Sea Fishing:** - $75 ___________________________________ About - The Drifter is a 60-foot long party fishing boat that has...

Bike Rental • Six Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Rent Bikes and Gear Accessories for your vacation! Duration 6 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Same Day E-Bike Rental • 9AM-4PM (up to 7 hours)

duration: up to 7 Hours 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...

After School Skate Club

Hilton Head Island Recreation Association

Book online
$100.00 - $600.00

duration: 4 Weeks • 1 Day Per Week • 2 Hours Each Day meeting_point: Island Recreation Center min_age: 7 max_age: 18 group_size: Up to 20 Campers description: Learn from one of the best and most experienced instructors on Hilton Head at the...

Adrenaline Package

Hilton Head Helicopter Tours

Book online
$100.00

pricing: $100 + Taxes/Fees description: Crank up the thrill and elevate your helicopter tour to the ultimate adventure with our doorless experience! Soar through breathtaking landscapes with the wind in your hair and unobstructed views that will...

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