Hilton Head, SC Vacations

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Featured Vacation Rentals

Family-Friendly Condo near the Beach w/ ...

Shipmaster 1805Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Shipmaster 1805 is a handsomely decorated, four-bedroom, three-bathroom townhome only half a...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Second row to the ocean - 5 bedroom newl...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in adore with this pretty South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Family-friendly condo with washer/dryer,...

Village House 106Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Village House 106 is a gorgeous two-bedroom, two-bathroom villa so close to the beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
First Floor Condo near the sound with be...

Spa On Port Royal Sound 3134Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head, this striking condo is the ideal beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Private pool - space for the whole famil...

This bright and roomy home, located on a peaceful cul-de-sac, has everything you will need to savor your next family adventure on Hilton Head!The pretty LIVING ROOM greets you as you enter through a two-story entry. With classy and comfortable...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Ocean Overlook - The Ultimate Vacation E...

LUXURIOUS DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 3RD FLOORING! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

2 Hour Lane Rental

Palmetto Axes

Book online
$45.00

Hit the Bullseye! Duration 2 Hours About Enjoy hurling axes as your friends or family marvel in your skills. Team up to see who the best pair is or compete individually in a winner take all (the glory and bragging rights) tournament. The...

Pumpkin Patch Express

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held the two Saturdays before Halloween each year. Riders will board the train for a 3-mile trip to the Pumpkin Patch. We will stop...

Electric Bike Hourly Rental (Walk Up)

Island Life Rentals and Tours

Book online
$50.00 - $60.00

duration: 1-6 Hours description: *Perfect for your day exploring around Hilton Head!* Additional Rates - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free - **Pick Up** - Free *All rentals must be returned within designated rental...

Kayak Tour of Jarvis Creek

Coastal Discovery Museum Hilton Head

Book online
$36.00 - $40.00

meeting_point: Jarvis Creek Water Sports description: *Look for for bottle-nosed dolphins, wading birds and other local wildlife!* ___________________________________ Duration 2 Hours (including safety training and...

Gift Card

Wheelz of Hilton Head

description: Purchase the perfect gift: a gift card with a value of your choosing!

Bike Rental • Three Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $80.00

duration: 3 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Hilton Head Sunset Cruise (2 Hours)

Hilton Head Boat Charters

Book online
$335.00 - $799.00

duration: 2 Hours cancellation_summary: We need at least 72 hours' notice for a full refund. meeting_point: 43 Jenkins Island Rd, Hilton Head Island, SC 29926 group_size: Up to 20 People description: Experience the very best that the waters of the...

Hilton Head -> Savannah Daily Round Trip Ferry
Book online
$19.99 - $99.00

duration: 45 Minute Ferry Time Each Way 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 description: Hilton Head -> Savannah Daily...

DIY Custom Sneaker Painting

Color Me Greenville

Book online
$45.00

duration: 3 Hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 pricing: Charms and Accessories vary in prices. You can view our options in person along with pricing.: Shoe Charms:($1-$10) Color laces: Variable ($2-$10) Pre-made...

Native Plant Sale

Coastal Discovery Museum Hilton Head

description: Come and join us for the next Coastal Discovery Museum annual Native Plant Sale in October 4th from 10 am - 1 pm. The sale will take place at the Coastal Discovery Museum on the Honey Horn grounds. Over 90 species of native plants will...

One Week Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99

description: Rate 7 Day Rental: $149.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration One Week (7 Days)

Sunset Cruise

Captain Moto Adventures

Book online
$350.00

description: Join us for a sunset on the water! Duration 2 Hours About Join us for a beautiful sunset cruise. The boat confortable seats 6. All ages and families welcomed on this private charter. What to...

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