Hilton Head, SC Vacations

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Featured Vacation Rentals

Perfect Location for a Family Vacation!

This incredible two-story Hilton Head vacation rental has been newly painted throughout and features a freshly refreshed first-floor bathroom with a new tiled walk-in shower. It’s conveniently located just a short bicycle ride to the beach and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beautiful Condo with Screened Porch, Sha...

Tennismaster 506Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note the Tennismaster pool is closed as of 9/25/2025. Renovations will begin...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Desired Resort on Hilton Head Island (3 ...

Substantial 3 bedroom/3 bathroom condo with nice kitchen, living and dining room, with a roomy deck over looking the pool. Recently refreshed bathrooms in January 2023.Ability to savor the amenities of the Westin Resort and Spa, which includes a...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Steps to the Beach • Palmetto Dunes 4?...

Beachside HomeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stay just steps from the beach in this comfortable four-bedroom home located in Palmetto Dunes...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Beachy condo near the ocean with a furni...

Forest Gardens 23Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This adorable condo is ideal for your next family beach hideaway or charming getaway! Located...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Stylish Island Gem – Just steps from p...

Seascape 3227: Stylish Tri-Level Townhome – Just a 5-Minute Stroll to the Beach!Book Direct for the Finest Prices & Feel!Professionally managed by Vacation Time of Hilton Head, Seascape 3227 promises a seamless booking experience and a stay...

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

Hilton Head Tours & Activities

Shark Fishing Excursion

May River Excursions

Book online
$375.00 - $775.00

*Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* Rates are per private charter **2 Hours** - $350.00 **3 Hours** - $450.00 **4 Hours** - $550.00 **5 Hours** - $650.00 Each additional passenger over 6...

2 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$18.00 - $100.00

duration: 2 Days meeting_point: Hilton Head Island, SC description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day...

Two Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$2.00 - $448.00

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...

Seafood Fest Try Archery

Hilton Head Island Recreation Association

Book online
$30.00

duration: 2 Hours meeting_point: Mid-Island Tract min_age: 7 group_size: Up to 30 people description: Take aim at Seafood Fest's Try Archery Event! Outdoor Rec's USA Archery certified instructors will provide you with basic instructions to try...

Private / Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$243.00 - $319.00

duration: 1.75 to 2 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. group_size: Max of 6 (Check Out Our Rentals for Larger Groups) accessibility...

Hack, Snack and Roadie Ride

Daufuskie Marsh Tacky Society

Book online
$450.00

Duration 3.5 Hours Please Note This is experience is designed for novice or better riders who are comfortable with longer hours in the saddle and are able to independently mount/dismount their horses easily, this culinary and riding adventure...

Full Moon Glow Bike Tour

Glow Bikes Hilton Head

Book online
$41.00 - $50.00

Experience the enchantment of our Full Moon bike tour on glowing bicycles! Overview Unique moonlit tour on glowing bicycles 3 picturesque stops at Hilton Head Island landmarks Perfect for individuals, couples, families, and groups Create...

2-Hour Sunset Sail

BC2 - Island Head

Book online
$19.99 - $99.00

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

Donuts with Dolphins Aboard Dolphin Seafari

Rates - Adult - $45 - Children -$26 (12 & under) $10 Infants (2 and under) ___________________________________ Duration - 1 hour and 30 minutes ___________________________________ About When you're on vacation, you want to relax, but...

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 ...

One Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$25.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Pumpkin Patch Express

The South Carolina Railroad Museum

Book online
$17.00 - $120.00

duration: 1.5 - 2 Hours 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...

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