Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanfront resort condo with WiFi, balco...

Sea Side Villas II 252Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Serenity by the sea awaits at this one-bedroom condo at Sea Side Villas! Centrally...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Heartwarming home with firepit, gas gril...

Wood Duck DelightOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Hilton Head, your next vacation destination for all things calming! You'll be...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Ground level condo with pool, golf & Sea...

Plantation Club 464Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel Hilton Head to the fullest in this adorable condo sporting golf course vistas! From...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Amazing & newly updated Palmetto Dunes R...

Stunning 4-Bedroom Lagoon-Front Retreat in Palmetto Dunes — Steps from the BeachCurrently being refreshed, progress photos shown! New photos coming soon! Appreciate one of the most spectacular vistas in all of Palmetto Dunes from this freshly...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
Lovely and Large Two Bedroom Villa at th...

You'll appreciate this pretty two bedroom villa located in Queens Grant Village within the heart of Palmetto Dunes. This Queens Grant villa is centrally located, providing very painless access to the Palmetto Dunes Tennis Center, Robert Trent Jones...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Bright and spacious home in Sea Pines,  ...

17 Sand Fiddler RdOur 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 family hideaway in Hilton Head, SC! This immaculate and bright home...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Outside DMC Partner Outing - Hilton Head Departure

description: *MUSIC | FOOD | FUN | & MORE* Outside DMC invites our partners to showcase Outside's OHANA & PAGE ISLAND! Join us for music, food, games, and more, and learn about the ultimate destination experience for your clients! Check-in will...

Surf and Sail Camp

Hilton Head Island Recreation Association

Book online
$275.00

duration: 4 days • 3.5 hours per Day meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 min_age: 7 max_age: 15 group_size: Up to 20 Campers description: Join us for an exhilarating 4-day camp combining the thrill...

Private Morning Half Day Sail On Knot The Office

Anchors Away Sailing Charters

Book online
$1,050.20

duration: 4 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 people accessibility: Limited Handicap accessibility, Please call us to ensure we can...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

description: Explore Coligny and its culinary offerings! Duration 2 hours and 30 minutes What's Included: - All tastings (amounts to a whole meal) - A fun and informative tour of the Coligny area About We will meet at our first location...

Sunset & Fireworks Tour

duration: 2.5 hours cancellation_summary: All reservations are subject to our 24 hour cancellation policy! group_size: Up to 12 people description: Experience the Magic of Summer Nights! Every Tuesday, Harbour Fest lights up the sky -- and there's...

North Pole Express

The South Carolina Railroad Museum

Book online
$17.00 - $22.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual holiday ride. Santa walks through the train and comes to you. No lines! The ride lasts about 90 - 120 minutes, or...

Bike Rental • Four Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Rent Bikes and Gear Accessories for your vacation! Duration 4 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Jet Ski Creek Run Tour

Lowcountry Watersports

Book online
$199.00

duration: 2 hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 6 description: Get ready for an exhilarating...

Bonfires & Weenies at The Landing

duration: 3 hours max_age: 101 group_size: 200 description: ???????? Bonfires & Weenies Season Is Almost Over! ???????? We’ve got TWO more cozy weekends left before we close for the season — so if you haven’t made it out yet, now’s the...

Flatout Crazy - Inshore/Nearshore Trip
Book online
$350.00 - $1,095.00

description: Best Fishing Guides in Murrells Inlet and Myrtle Beach Area Rates - **Half Day Trips:** Pricing includes 2 passengers - $50 per additional person - **Full Day Trips:** Pricing includes 4 passengers - $75 per additional...

Solaris - Sandbar Sunbathing Charter (7 to 10 passengers)

duration: 3.5 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Book a luxurious charter aboard Solaris to the Sandbar only accessable by boat! Escape to paradise with our exclusive 3.5-hour charter aboard...

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...

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