Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Home with private pool, fenced in yard a...

Sunshine ShamrockOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this impressive home with a private pool and a fenced-in backyard, ideal for a...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
1st Floor Condo with Pools,Hot tub, 100 ...

Island Club 1102Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway at The Island Club of Hilton Head! This appealing first-floor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunlit Oceanfront Condo with Two Balconi...

Windsor II 2419Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'When you're looking to get away for fun in the sun, this Windsor II condo is the place to stay...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Bright, beachy condo with pools, hot tub...

Barrington Arms 107Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Everyone needs a bit of salty air and sun-kissed skin, so make your way to the pretty...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Perfect condo across street from beach a...

Seascape Villas 3215Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal beach hideaway in Hilton Head! This striking condo offers a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious Palmetto Dunes condo with priva...

St Andrews Common 1873Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in Hilton Head, SC! This striking condo located in...

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

Hilton Head Tours & Activities

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy beverages of...

2 Hour Wambaw Creek Wilderness Area Blackwater Tour
Book online
$55.00 - $110.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Crabbing

May River Excursions

Book online
$300.00

*Our most interactive and famous excursion!* ___________________________________ Rates **Private Charter** - $300 for 6 people or less. *(Can hold up to 12 people for extra charge, call for more...

Solaris - Happy Hour Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Book a luxurious charter aboard Solaris today! **Our private charters accommodate up to 10 passengers, ensuring an intimate and personalized...

Life Under the Sea

Coastal Discovery Museum Hilton Head

Book online
$5.00

There is a magical world full of fascinating creatures under the sea! Join knowledgeable Museum staff and volunteers in the Discovery Lab to explore, touch, create, play, and learn more about ocean life. Who lives in those shells? What does a crab's...

Solaris - Sunset Cruise (up to 6 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **Our private charters accommodate up to 6 passengers, ensuring an...

Private Party

Palmetto Axes

Get the joint all to Yourself! About *Ages 12+ • Up to 36 People* All the fun for you and as many people as the fire marshal will let in the place. Book 2 plus hours and save even more! - Bring in your own food - Maximum of 36 people per...

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.

Bunch Bike - Family E-Bike Fun!

Pedego Electric Bikes Greenville

Book online
$109.00

duration: 6 to 8 Hours meeting_point: Pedego Electric Bikes Greenville. Located at Hampton Station - 1320 Hampton Ave Ext. STE 11A Greenville, SC 29601 description: Experience family fun like never before! ???? Experience the Thrill of...

Equestrian Lessons - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

3 Hour Fishing Charter

Awesome Adventure Charters

Book online
$510.00

Better Suited for Older Children or Those Who are Negotiating a Tighter Schedule Duration 3 Hours About Whether going for that trophy fish, pursuing world-class tarpon in the ocean, or enjoying the scenery while fishing the salt marsh...

Stand Up Paddle Boarding Tour

Hilton Head Island Recreation Association

Book online
$40.00

duration: 1.5 hours meeting_point: Rowing and Sailing Center description: Your 1.5hr stand up paddle board trip will explore the marshes of Skull Creek. An educational Lowcountry experience learning and working with the tides, oysters, and...

Find your perfect Hilton Head

Fishing Charter

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