Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Marriott Vacation Club Villa

This property is located in Hilton Head. The public area overlooks the water but there is no beach access. However there is a shuttle that takes guests to the beach for no charge. You just call for a pick up! There is on-site parking, elevators to...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beautiful 3 bed home overlooking the gol...

HILTON HEAD ISLAND. This handsome home overlooking the Robert Trent Jones golf course offers a great layout and striking outdoor space for the entire family. With three bedrooms and three bathrooms, this home has plenty of space for you and your...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Expansive Private Oceanfront Home with V...

Fall in adore with this broad oceanfront home located on the Atlantic Ocean in handsome Palmetto Dunes Oceanfront Resort! As you enter you are welcomed by a grandiose staircase and wood floors leading to the kitchen, dining and living areas. The...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Ocean Overlook - The Ultimate Vacation E...

LUXURIOUS DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 3RD FLOORING! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Newly-renovated condo w/ lagoon views, s...

Evian 232Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'The whole family will savor staying at this bright, freshly-updated, ground-level condo overlooking a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
3 Bed/3 Bath Villa on the Fourth Floor w...

Discover the beauty of Hilton Head Island with striking ocean and beach vistas from the private balcony of one of our oceanfront villas. Choose from cavernous 1, 2, or 3-bedroom villas in a variety of floor plans, each offering a comfortable...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Five Day Electric Bike Rental
Book online
$250.00

duration: 5 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Six Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$800.00

Duration 6 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, Cobia, Sharks! 6hrs gives us time to target a couple different species, more fishing time, more spots...

10 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$42.00 - $295.00

duration: 10 Days description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours self pick up and drop off available...

Two Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$40.00 - $200.00

Rent with us! Duration 14 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and attachments

One Day (24-Hour) Golf Cart Rental

Wheelz of Hilton Head

Book online
$240.00 - $320.00

Golf Cart Rentals! Duration 24 hours Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online due to...

Fishing Charter - Kahuna

Native Son Adventures

Book online
$365.00 - $1,260.00

Duration 3 to 8 Hours About In-Shore and Near-Shore Fishing. The most stable adventure vessel on Hilton Head Island! The 26 foot Glacier Bay catamaran is the cream of the crop! He does it all, so let’s go have some fun! Bean bags lots...

PB 2 Hour May River Kayak Nature & History Paddle

On this casual tour, you'll explore the local creeks with a naturalist guide. No kayak experience is necessary. Duration 2 hours Meeting Location - This activity will meet at the Paddle House which is located underneath the Canoe Club...

Hunting Island and the Holidays

Hilton Head Island Recreation Association

Book online
$25.00

duration: 2hrs meeting_point: Hunting Island State Park group_size: Up to 20ppl description: A wonderful Moore to Life Holiday tradition filled with nature, food, shopping and fun with friends! We'll begin our day at the Hunting Island Nature...

Hidden Treasures Tour

Hidden Treasures Bluffton

Book online
$20.00 - $500.00

Come and discover the Hidden, but not Forgotten Treasures of Historic Bluffton. Duration 45 Minutes About We will discover long lost Hidden Treasures in and around Beautiful Old Town Bluffton. More info There is a 4 person minimum...

Golden Hour Sunset Sail

BC2 - Island Head

Book online
$19.99 - $99.00

duration: 2 Hours meeting_point: Board Creek Marina 18 Simmons Rd. description: Smooth sailing, stunning views, and something for everyone. Golden Hour Sail is a luxury sunset experience designed for all kinds of groups—families, friends, couples...

Native Plant Sale

Coastal Discovery Museum Hilton Head

Come and join us for the next Coastal Discovery Museum annual Native Plant Sale in October 4th from 10 am - 1 pm. The sale will take place at the Coastal Discovery Museum on the Honey Horn grounds. Over 90 species of native plants will be...

1.5 Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$53.99 - $69.99

Single Kayak 1.5 Hour Rental: $43.99 ________________________________ Double Kayaks or Canoes 1.5 Hour Rental: $56.99 __________ Triple Canoe 1.5 Hour Rental: $69.99

Find your perfect Hilton Head

Fishing Charter

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