Hilton Head, SC Vacations

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Featured Vacation Rentals

Stunning, coastal chic two bedroom, two ...

Stunning coastal chic two bedroom two bathroom villa! Come and relax in this newly refreshed and decorated 1st floor villa in Palmetto Dunes Oceanfront Resort within the Centre Court complex. Savor peaceful mornings on the porch overlooking the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beautifully Decorated First Floor Condo ...

This Hilton Head beach condo has broad ocean, lagoon and tropical garden vistas! Well decorated and located on the 1st floor for simple access, this villa comfortably sleeps five. The kitchen has refreshed cabinetry, granite countertops, stainless...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Enjoy 4 rounds of golf per day!!!!!!!

A handsome Labor Day week on sunny Hilton Head Island. Appreciate this stand alone home in a pretty gated community. Beach access, Tennis, 28 rounds of golf for just the cart fee, 2 pools, and hot tub. Book now,

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
2-story condo with on-site pool, golf, t...

Harbour Master 503Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make the most of Carolina coastal living at this splendid Harbour Master condo at Shipyard...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Wonderful condo right up from the beach ...

Island Club 6203Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just steps away from the beach and with vistas of the lagoon from the private, furnished...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Well Updated with Beach Contemporary Dec...

This refreshed, delightful two bedroom, two bath villa is located directly beside the Robert Trent Jones Driving Range and Clubhouse and is also just steps to the pool! You will feel instantly on vacation as you enter this coastal villa! The warm...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Sweetgrass Basket 3-Day Workshop

Coastal Discovery Museum Hilton Head

Book online
$425.00

March 19, 20, 21, 2025 from 9:30-12:30 on each date. World-famous but with origins right here in the Lowcountry, the Sweetgrass basket is one of the region’s best known art forms and cultural icons. Learn about the history of sweetgrass basket...

2.5 Hour Hilton Head Guided Boat Tour

Bluewater Adventure - Hilton Head

Book online
$115.00 - $149.00

Rates - Adults - $135 - Children - $115 - Fireworks Tour every Tuesday night - $135 ___________________________________ Duration 2 hours and 30 minutes ___________________________________ Guided boat tours offered daily! Adventure...

Three Hour Dolphin Strand Feeding Search

Hilton Head Island Tours

Book online
$375.00 - $395.00

*Dolphin Strand Feeding is a unique and exciting behavior developed by local Atlantic Bottlenose Dolphins!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages...

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

One-of-a-kind photo opportunity in a beautiful Lowcountry setting at the Stoney Baynard Ruins Duration - Up to 60 minutes, with most shoots lasting about 45 minutes Overview Are you looking for the perfect Hilton Head family...

Three Day Surf Board Rental

Hilton Head Outfitters - Bike Rental

Book online
$89.99

Rate 3 Day Rental: $89.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 3 Days

Beach Gear Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $75.00

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 than 5PM. ...

Ten Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $400.00

Electric Bike Rental Duration 10 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all without...

Glow in the Dark Splatter Session

Color Me Greenville

Book online
$50.00

duration: 45 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 group_size: 6 Max description: It’s your invite to light up the night and vibe out! Experience the thrill of our glow-in-the-dark nights, where we...

Morning Segway and Coffee
Book online
$115.00

Start your day on a caffeinated Segway ride! Duration 1.5 Hours About 50% Segway. 50% Coffee. 100% Fun! Join us for this fun & unique way to explore Hilton Head Island! This 2.5 hour tour will be one of the highlights of your vacation...

Full Day Ocean Kayak Rental

Hilton Head Outfitters - Bike Rental

Book online
$75.00 - $90.00

Single Kayak 8 Hour Rental: $75 ________________________________ Double Kayaks or Canoes 8 Hour Rental: $90

Weekend 9:30 am-3:30 pm Golf Cart Rental
Book online
$70.00 - $90.00

Weekend 9:30 am -3:30 pm - Golf Cart Rental *Must have valid Driver's License to rent a cart.*

Surfboard Rentals

Hilton Head Island Recreation Association

Book online
$25.00 - $140.00

duration: 2-8 Hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 description: Our surfboard rentals have you covered! Whether you're a seasoned surfer or just starting out, we offer a wide range of...

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