Hilton Head, SC Vacations

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Featured Vacation Rentals

The Hedges D1 | Condo in Hilton Head wit...

The Hedges D1Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'So much is within an painless walk of this first-floor condo at The Hedges, from a gorgeous...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Large Two Bedroom Villa with Ocean Views...

You'll savor this generously designed and comfortable two bedroom Windsor Place condominium with ocean vistas! The kitchen features granite countertops and is entirely-equipped with everything you'll need for a home cooked meal. Looking out from...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3133 Villamare - Direct Oceanfront Views...

This handsome Villamare condominium is directly oceanfront! The Kitchen contains bespoke cabinetry, granite countertops, bar seating for three and is completely equipped to meet your family's cooking needs. Just beyond the Kitchen is the Dining...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Second-floor condo with pool access, bal...

Sands Village A2EOur 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 impressive corner condo is just a...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
1st Floor condo with balcony, pool, clos...

Lighthouse Tennis 2376Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate coastal lifestyle in this striking condo located within Sea Pines in...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
12 Whelk, Steps to the Beach, Private Po...

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this freshly remodeled four-story property offers impressive...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

Beach Gear Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Everything you need for a fun and comfortable day at the beach! Duration 6 Days 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. ...

Private Family Or Group Fishing Trip Aboard The Drifter

duration: 3 Hours cancellation_summary: 72 Hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way group_size: 32 people pricing: The Private Family or Group Fishing Trip Aboard the Drifter has a set price of $995 for a group size of 16 people or...

Outdoor Discovery Homeschool

Hilton Head Island Recreation Association

Book online
$40.00 - $800.00

duration: 1 Day per week for 1.5hrs meeting_point: Island Recreation Center min_age: 7 max_age: 14 group_size: Up to 14 Campers description: Outdoor Discovery Homeschool is a hands-on, nature-based learning program led by our Master Naturalist...

Eight Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$2.00 - $141.99

8 Day Rental Rates: - 16” Kids Beach Bike: $65.99 - 20” Kids Beach Bike $65.99 - 24” Youth Beach Bike: $65.99 - 26” Bike w/ Child Seat: $80.99 - 26” Mens Beach Bike: $65.99 - 26” Unisex Beach Bike: $65.99 - 12" Balance Bike: $65.99 ...

Marriott Vacation Club Dolphin Eco

Outside Hilton Head’s Dolphin Eco Tour is one of the most popular tours on Hilton Head Island, providing an unforgettable experience for nature lovers, families, and anyone looking for a fun and educational adventure on the water

Hilton Head Yacht - Day Cruise

Hilton Head Yacht Charter Company

Top Shelf Yacht Charters are all about you. From adventure to anniversaries, relaxing to proposing, there's nothing we can't do for you during your cruise! Imagine your own floating resort! Experience 80 feet of pure opulence aboard Top Shelf. Our...

Three Hour Inshore Fishing Trip

Hilton Head Island Tours

Book online
$445.00 - $495.00

*Three Hour Inshore Fishing Trip* ___________________________________ Rates **Up to Four Guests** - $445.00 **Five Guests** - $475.00 **Six Guests** - $495.00 ***All ages welcome! | Maximum of 1200 lbs*** ___________________________________ ...

Betty

Slow Rides LLC

Book online
$300.00 - $5,000.00

Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. North East...

2-Hour Day Sail

BC2 - Island Head

Book online
$19.99 - $49.99

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Day with a Native - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

Duration 3 to 8 Hours (prices may be subject to change due to rising fuel prices) 1.CREATE YOUR OWN DAY! Pick your top three interest’s and we will try our best to make them happen- Choose from Fishing, Birdwatching, Beach-combing...

Solaris - Morning Sightseeing Cruise (up to 6 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book a luxurious morning charter aboard Harbour Town's Solaris now! **Our private charters accommodate up to 6 passengers, ensuring an intimate and...

Donation

Coastal Discovery Museum

Book online
$25.00 - $1,000.00

*Donate Today!*

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