Hilton Head, SC Vacations

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Featured Vacation Rentals

19 Sand Dollar, Luxury 2nd Row Home, Che...

19 Sand Dollar, Hilton Head Island. Welcome to this appealing second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, savor plenty...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Updated Condo with shared tennis, close ...

Xanadu A10Our 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 newly updated 3rd-floor condo, accessible...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Close to the Beach! 3 Bed 3 Bath Townhou...

New to Island Getaway - great weeks availableHILTON HEAD ISLAND. The ideal location in Palmetto Dunes is available to you! At the end of the complex just off the beach path, you won’t find a better spot! The first thing you will notice upon entry...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Relaxing condo with furnished balcony, o...

HH Beach & Tennis 248COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in Lowcountry coastal leisure at this Hilton Head condo. Soak up the generous...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
2nd Row Palmetto Dunes 5 Bed/5 Bath Home...

Located at the end of the street with direct beach path access from the pool, just 2 mins. from the striking beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Appreciate countless sunny days by the pool and calming...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
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 refreshed four-story property offers striking...

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

Hilton Head Tours & Activities

One Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$60.00

Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a small motor engages and gives you a boost, so you can zip through...

Crescent City Cocktails: A Taste of New Orleans

Step into the spirited traditions of New Orleans with this hands-on cocktail class celebrating the classics that made the Crescent City a cornerstone of cocktail culture. From refined sippers to bold, celebratory pours, this experience channels...

21 Day Rental

Island Life Rentals and Tours

Book online
$75.00 - $555.00

___________________________________ 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...

Sallie Ann Authentic Gullah Tour

Daufuskie Island Gullah Heritage Society

Book online
$70.00

See and enjoy a Gullah Tour on Daufuskie through the eyes and memories of a sixth generation Gullah native! Duration 3 Hours About We are a non-profit organization. Take a relaxing boat ride to Daufuskie, where you will be greeted at the...

Three Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$661.00

Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a small motor engages and gives you a boost, so you can zip through...

2-hour Afternoon Sail and dolphin watch Seas The Moment - Our newest boat

*Afternoon Sail* Generally a breezy afternoon leading to some of our most exciting sailing all day. Come and experience true sailing without running the motor. Take the helm and help with handling sails if you desire, but either way, kick back...

One Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$20.00 - $100.00

Rent with us! Duration 7 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and attachments

Private Inshore Charter Fishing aboard Hobo

The "Hobo" is a Coast Guard inspected 27' Carolina Skiff available for private charters. Please Note 6 passengers are included in the rate. Each additional passenger is $65 About The "Hobo" is licensed to take up to 16 passengers making this...

Pumpkin Patch Express

The South Carolina Railroad Museum

Book online
$17.00 - $120.00

duration: 1 Hour 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 the...

Gift Card

Island Skiff Adventure Tours

Beach Gear Rental • Two Days

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 48 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. ...

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...

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