Hilton Head, SC Vacations

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Featured Vacation Rentals

108 Beachwalk Pet Friendly Condo, Steps ...

When you walk in the front door you are greeted with an open floor plan and vaulted ceiling. The master bedroom has an en suite and is appointed with a king size bed, flat screen tv and a sitting area for those calming days for reading. This...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
2 bedroom 2.5 bathroom townhouse- walkin...

**While this rental is dog-friendly, only 1 non shedding dog under 40 lbs will be considered, let Island Getaway know if you are bringing a dog so the fee can be added. An additional non returnable fee of $150 will be in addition to the price...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Stunning Hilton Head Island Vacation Ren...

Welcome to your ideal beach getaway! Located less than a mile from the South Gate of Palmetto Dunes Oceanfront Resort and just a short walk to the ocean, this elegantly refreshed 4-bedroom, 3-bathroom ranch-style home offers the ideal blend of...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Dog-friendly ocean view oasis with pool,...

Summary:Ocean DreamThe Space:Swim right up to the edge of luxury at this memorable ocean view home featuring a private heated pool and three tiers of coveted indoor/outdoor living and entertaining space. An on-site pathway leads directly to the...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Palmetto Dunes condo with shared pool, p...

Summary:Turnberry Village 261The Space:Feel the ultimate island getaway at this extravagant 2-bedroom, 2-bathroom condo located near the esteemed George Fazio golf course in Hilton Head, SC. With access to fresh Palmetto Dunes amenities, including a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Brand New Retreat Private Pool & Golf Si...

Summary:Escape to heaven where there is plenty of space for family and friends in this three-story townhome in The Homes at Olive Shell. The 4-bedroom home sleeps up to 10 guests and features two king bedrooms, two queen bedrooms, a private plunge...

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

Hilton Head Tours & Activities

Six Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

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...

Adopt-a-Dolphin

Coastal Discovery Museum

Book online
$50.00 - $100.00

description: About Sixty percent of all adoption money goes directly to the scientists who are studying these magnificent mammals and helps fund interns studying these dolphins, boat fuel, and supplies needed for the Marine Sensory and...

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...

Sip & Sunset - BYOB Adults Only Dolphin Cruise

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 21 max_age: 99 accessibility: Boat is...

Santa’s Twilight Express

The South Carolina Railroad Museum

Book online
$27.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual twilight holiday ride. Santa walks through the train and comes to you—no lines! As we travel down the tracks, the...

Ultimate Dolphin Experience

Lowcountry Watersports

Book online
$16.95

Private Gullah Heritage Trail Tour Requests

Gullah Heritage Trail Tours

Book online
$28.00

description: *Gullah people are known for preserving more of their African linguistic and cultural heritage than any other African-American community in the United States.* ___________________________________ Duration 2.5 hours...

Trail Rides Experience - Montage Guests

duration: 1.5 hours meeting_point: Longfield Stables Trail Barn min_age: 8 group_size: Up to 5 people description: Embark on an unforgettable experience through the scenic Lowcountry of Palmetto Bluff. Our expertly guided rides take you through...

5 Day Rental

Island Life Rentals and Tours

Book online
$27.00 - $195.00

duration: 5 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Fireworks & Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$69.75 - $395.00

duration: 3 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the...

WAHHI Vanishing Island Beachcombing Cruise

meeting_point: Hilton Head Island, SC description: *Meet Hilton Head's dolphin population and visit a vanishing island. Collect shells and observe local wildlife. A Lowcountry favorite!* --- Description This three-hour boat cruise...

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