Hilton Head, SC Vacations

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Featured Vacation Rentals

Ideally located condo with pool, tennis ...

Summary:Beckenham 103The Space:Beckenham 103 is an charming condo in Port Royal Village, just a fast walk to the beach. For even faster transportation, you'll have access to two bicycles. There is a lot to boast about with exceptional upgrades...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Wonderful Townvilla with pool, tennis an...

Summary:Ocean Gate Villas #5The Space:Feel the ultimate Hilton Head Island hideaway at this striking villa located in the Ocean Gate community. Located at the base of South Forest Beach Drive, this beautiful villa offers the ideal blend of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Large Golf Course View Home with Large P...

This handsome home features extravagant wide plank, hand-scraped, black walnut floor throughout the main living areas. This impressive home consists of six bedrooms, six and a half bathrooms along with an delightful sunroom along with a enchanting...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Gorgeous fifth floor oceanfront unit

HILTON HEAD. This extravagant oceanfront complex offers the ultimate in resort vacation accommodations. You have a wide selection of 2 or 3 bedroom villas with vistas ranging from landscape to oceanfront, roomy floor plans, designer decorated...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Coastal charm villa with golf-course vie...

Summary:Escape to luxury at this impressive two-bedroom, three-bath end-unit condo located along the photogenic Robert Trent Jones Oceanfront Golf Course in Hilton Head, SC. Appreciate peaceful golf-course vistas, bright open living spaces, and...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
27 Lagoon Road-4 bedroom w/ Pool. Walk t...

Welcome to your ideal coastal hideaway at 27 Lagoon Road! This cavernous 4-bedroom, 2.5-bathroom home offers the ideal blend of comfort, convenience, and relaxation. Savor sunny days by your private pool, relax on the patio, or take a short walk to...

  • Hilton Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

Wine & Mead Tastings

Honey & Thistle

Book online
$25.00

duration: 1 Hour min_age: 21 description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore small-batch wines and...

Riverside Lounge

Vintage View River Retreat

Book online
$5.00 - $125.00

duration: 5 Hours description: Our new Riverside Lounges take the traditional park picnic experience and elevate it to a premium, private basecamp on the banks of the Pacolet River. Each lounge is thoughtfully designed to provide a comfortable and...

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

Pontoon Rental • 50 Horsepower
Book online
$300.00 - $2,700.00

description: Full Day Boat Rentals Know Before You Go - All renter's must be 21 years or older. - Can fit up to 10 people. - No pets allowed. - We are unable to provide life jackets for kids under 90 lbs. - All of our vessels are 50...

Monkey Safari

Hilton Head Helicopter Tours

Book online
$369.00

description: Fly north from Hilton Head toward Morgan Island (Monkey Island) for scenic aerial views of the Lowcountry coastline and abundant wildlife. Keep an eye out from the helicopter for dolphins, sharks, and sea turtles as your experienced...

Beach photography Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

duration: 10–15 minutes cancellation_summary: Full refund if photographer cancels for weather; rescheduling attempted first. meeting_point: 55 Starfish Dr, Hilton Head Island, SC 29928 description: If you are looking for a photoshoot but don’t...

Curator's Tour

Coastal Discovery Museum Hilton Head

description: Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg and...

Sunset Mini Boat Dolphin Tour

Lowcountry Watersports

Book online
$249.00

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: 5 group_size: 2, 3, or 4 per mini...

HH Seafood Festival: Ohana Fireworks Cruise

description: A special cruise on the luxury power catamaran, Ohana. This leisurely sunset dolphin cruise will end with the best seat in the house for the fireworks show! Departing Saturday, February 26th 5-7pm $115 per person (includes Kettle One...

Upper Wando River Kayak Tour

Nature Adventures Outfitters

Book online
$25.00 - $110.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Full Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$99.99 - $125.99

description: Single Kayak Full Day Rental: $99.99 ________________________________ Double Kayaks Full Day Rental: $125.99 _____ Duration 8 Hours (Boats must be back by 4pm each day)

Paddleboard Rental

Wateree Marina

Book online
$25.00 - $50.00

description: Paddleboard Rentals What to Bring - Valid Driver's License - Major Credit Card

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