Hilton Head, SC Vacations

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Featured Vacation Rentals

2 bedroom 2 bath townhouse overlooks the...

HILTON HEAD. Guests have a choice of multiple 2 and 3 bedroom townhouse floor plans. These secluded villas have plenty of living space, full kitchen facilities, decks, and patios. They are located along the fairways of the Fazio golf course in...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanside Oasis - Breathtaking Views and...

Appreciate the best of Hilton Head Island in this charmingly located condo, just a short walk from the fashionable Coligny Beach. You’ll be close to amazing dining, shopping, entertainment, and the vibrant Low Country Celebration Park.Located in a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Marriott Grande Ocean Resort, July 31-Au...

Treat your family to a remarkable vacation at Marriott's Grande Ocean. They are a brief walk from the beach, and near superb shopping and dining locations. Explore first-class luxury at Marriott's Grande Ocean for the ideal vacation hideaway...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
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
Beautiful lagoon views, new living room ...

Welcome to your coastal getaway in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island! This gorgeously appointed 4 bedroom, 4 bathroom townhome offers the ideal blend of indoor comfort and outdoor tranquility, attractively located...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Charming bay view villa with pool, washe...

Harbourside 7126Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'There's something here for everybody at this splendid villa! If you're a fan of music, you'll...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Bachelorette Booze Cruise Party

Unwritten Charters LLC

Book online
$1,200.00

Enjoy a Private Cruise for that special event! Duration 4 Hours About Is the stress of planning your big day getting to you? Why not get together with all of your friends on a private cruise around Charleston Harbor on one of our luxury...

Sunset Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

Stunning Sunset Views About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Stunning sunset views over the water and...

Two Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$25.99

Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

Director's Walk

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $25.00

*Visit Honey Horn with the Museum's Director.* ___________________________________ Duration 1.5 Hours ___________________________________ About Walk the shell path and Nan Lloyd Trail with the Museum director and discover some of the...

Indigo Tie Dye Party

Coastal Discovery Museum Hilton Head

Book online
$15.00

Come and join in the tie dyeing fun! Twist, twirl, tie, and dye with natural indigo dye. Why indigo dye? In 1739 Eliza Lucas Pinckney’s experiments with the indigo plant resulted in a very profitable cash crop for South Carolina. Enjoy a fun...

Hilton Head Farmer's Market

Coastal Discovery Museum Hilton Head

Rebuild our local food economy! _____________________ Description: Visit the Hilton Head Farmers Market at the Coastal Discovery Museum every Tuesday from 9:00am - 1:00pm. Take home fresh local produce, pasture raised chicken, free range rabbit...

Shrimping

May River Excursions

Book online
$300.00 - $400.00

*Experience sea life like never before!* ___________________________________ **Please note**: Shrimping is only available from August-December ___________________________________ Rates **Private Charter** - $300 2 hours (for 6 people and...

SCM Private SUP Yoga
Book online
$60.00 - $225.00

duration: 1.5 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head Island min_age: 12 group_size: 10 pricing: $225 for up to first 3 people $60 each additional person description: Find your flow where the river meets the sky...

Six Hour Private Offshore Charter
Book online
$1,200.00

*Let’s head out to some reefs for great fishing!* ___________________________________ Rates **Private Charter (All Ages | For up to 6 guests):** $1200 About Our Hilton Head Island waters provide some of the best fishing in the world...

Cinco de Mayo…..The YoCo LoCo way!

About Hop aboard for a fiesta on wheels! We will kick this tour off at The Print Shop, Fort Mill. Enjoy great beer and beautiful outdoor seating. We will cruise over to Tony’s Cantina in Riverwalk to enjoy margaritas and delicious bites. Last...

19' Stingray Rental

H2O Sports

Book online
$325.00 - $750.00

duration: 2-6 hour rentals cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Boat holds 6...

PB Freshwater Kayak Fishing

*We have pioneered kayak fishing on the east coast!* ___________ About This is one of the fastest growing sports and is offered in the Inland Waterway Trails at Palmetto Bluff. The Hobie Pro Angler kayaks allow access to areas where powers...

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