Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanview Condo with WiFi, Hot Tub, Pool...

Island Club 6304Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you want to swim in a exhilarating pool or hot tub, fish in a lagoon, or play five sets of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this cavernous 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Large Home with Panoramic Views of Rober...

Savor sweeping expansive vistas of multiple greens of the Robert Trent Jones Golf Course and a huge part of the 11 mile lagoon system! See the sunrise over the iconic 10th hole of Robert Trent Jones every morning! There are fantastic vistas from...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Relaxing condo with heated/chilled pool,...

Dunes Villas D4Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your freshly modernized condo in the heart of South Forest Beach on Hilton Head...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Beautiful condo with pool, tennis, balco...

Courtside 56Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideally located in the charming Coligny Beach area, this home is within walking distance of the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Gorgeous and sunny home with pool, beach...

Kingston Dunes 68Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sophisticated, modern, roomy, and private, the ideal Hilton Head Island hideaway exists, and...

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

Hilton Head Tours & Activities

PB Family Ski Day
Book online
$245.00 - $1,290.00

*Certified instructors will show you the ropes on this 2 1/2 hour program! Ski, tube, wakeboard and kneeboard.* _________ About Cruise from Palmetto Bluff back to our favorite ski grounds and learn how to water-ski, wakeboard, kneeboard, or...

Face Painting

Coastal Discovery Museum Hilton Head

Book online
$10.00

duration: 2 meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: Join us for a colorful and creative Face Painting experience! From fierce sharks to magical butterflies, our talented artist will bring Lowcountry critter...

Two Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$59.99

The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

9 Day Rental

Island Life Rentals and Tours

Book online
$39.00 - $275.00

___________________________________ Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles...

Cruise Through The Stars

Vagabond Cruise

Book online
$19.95 - $39.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Stroller and wheelchair accessible on the lower deck of the Vagabond description: ![Description of...

Shark Fishing Aboard the Drifter
Book online
$55.00 - $65.00

*Shark Fishing for the whole family on Hilton Head Island!* ___________________________________ Rates - **Adults:** - $65 **Children 12 and under** $55 ___________________________________ About - The Drifter is a 60-foot long party...

Small Group Tasting

duration: 1 Hour min_age: 21 group_size: 6-10 people description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore...

Dolphin Cruise

Carolina Breeze Charters

Book online
$275.00 - $350.00

duration: 2 hours meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Discover the best of beautiful Hilton Head Island, SC aboard the Carolina Breeze, a 31-foot yacht-class vessel...

Four Hour Rental (Walk Up)

South Beach Bike Rentals

Book online
$25.00 - $62.00

Enjoy miles and miles of scenic bike paths Duration 4 hours About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also available ...

Discovery Lab Open House

Coastal Discovery Museum Hilton Head

Rates Suggested $5 donation per person (Ages 4+). Children must be accompanied by an adult. Everyone must have fun!! Duration 2 Hours (Drop in any time during Open House hours and stay as long as you'd like!) Discovery Lab During the...

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...

Sunset Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

Stunning Sunset Views About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Stunning sunset views over the water and...

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