Hilton Head, SC Vacations

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2 bed villa with landscape view- Only a ...
4.7
(3)

HILTON HEAD ISLAND. Wendover Dunes is a beautiful oceanside villa complex that is just a short walk to the beach. Located next to the Barrington Enclave in Palmetto Dunes, these villas are delightfully decorated and equipped with all of the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Spring Getaway in Hilton Head, SC @ Marr...

Live your best life at Marriott's Barony Beach Club. Perfectly located on the impressive oceanfront of Hilton Head Island, South Carolina, our vacation rental beach resort offers the ideal backdrop for creating a lifetime of memories. Feel at home...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Bright, comfortable villa near beach wit...

Links 12BOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Links 12B is a light, bright, and roomy three-bedroom, three-bathroom villa located on Barony...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Adorable ocean side villa with large win...

Sealoft 2032Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get ready for adventure in this splendid little oceanside villa in what will be your next favorite...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Hilton Head Condo w/ Covered Balcony + P...

Leave your worries behind and stay at this newly refreshed 2-bedroom, 2-bathroom vacation rental condo in Hilton Head! Comfortably sleeping up to 6 guests, this unit is within walking distance to the beach, eateries, shopping, and more. You'll have...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront resort condo with WiFi, balco...

Oceanside Villas II 289Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to heaven at this welcoming condo in Hilton Head, SC, where memorable beach...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Glow in the Dark Splatter Party! - Deluxe
Book online
$50.00 - $695.00

duration: 1.5 Hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: Prices start at $375 for parties description: It’s your invite to light up the night and vibe out with your crew! Experience the...

Seasonal Fireworks Cruise

Flip Flop Charters

Book online
$775.00

Watch fireworks at Shelter Cove! Duration 3 hours About From June to August we offer a weekly cruise to watch the fireworks at Shelter Cove. You’ll have a front row seat to see the magic aboard! This three hour cruise is only on Tuesdays in...

Civil War Era

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $50.00

*Find out how the soldiers of the Civil War spent their time on the island!* ___________________________________ Duration 1 Hour ___________________________________ About During the Civil War, Hilton Head Island played a crucial role as the...

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...

Six Day Bike Rental

Wheelz of Hilton Head

Book online
$48.00 - $96.00

Six Day Bike Rental Rates Duration 6 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect getting around town...

Discovery Flight

Hilton Head Helicopter Tours

Book online
$400.00

duration: 1 Hour (30 minutes flight time and 30 minutes ground) meeting_point: 38 Gateway cirle HHI,SC 29926 min_age: 16 description: Get ready for the adventure of a lifetime with a Discovery Flight! This hands-on experience gives you the...

Parasailing

H2O Sports

Book online
$95.00

duration: 8-10 minutes per parasail ride • Up to one 1 hour for entire trip 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...

Three Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$45.99

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

Private Lesson with George Spinella

Palmetto Dunes Golf Academy

Book online
$90.00 - $450.00

About George Spinella George Spinella graduated from Siena College in 2003 and the San Diego Golf Academy in 2005. He is the 1st Assistant at the George Fazio Course and has been teaching with Palmetto Dunes since 2006. George enjoys teaching...

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Capture one of a kind Lowcountry portraits at the...

Ultimate Dolphin Experience

Lowcountry Watersports

Book online
$16.95

Glamp-out Weekend!

Vintage View River Retreat

Book online
$20.00 - $100.00

duration: 2 nights meeting_point: 250 Phifer Line Rd, Spartanburg SC 29307 min_age: 2 description: Have you ever wanted to go camping for the weekend but you didn't have the equipment or you didn't feel like you had the knowledge to do it? Then...

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