Hilton Head, SC Vacations

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Featured Vacation Rentals

Beautiful, dog-friendly villa with pool ...

Beachwalk 167Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’ll adore this gorgeous, entirely updated villa in the sought-after Beachwalk community! The...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
44 Mooring Buoy- 3rd Row (176 yard walk)...

You can practically feel the sand between your toes! This Palmetto Dunes island beauty is at the end of the beach path, so you’re just a few flip-flops or barefoot steps to the ocean and fun in the sun. The first-floor living area has a elegant...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Relaxing Evian Condo | Enjoy pool, golf,...
4.9
(12)

Evian 115Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this 2BR/2BA Evian Villas condo for a enchanting Shipyard Plantation hideaway. Relaxing...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Airy abode w/ beach access and balcony v...

Hampton Place 6506Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nothing screams vacation like salty air and warm island sun. The adventures available to...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront condo with beach access, outd...
3.3
(3)

Sea Cloisters 304Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel private ocean vistas and on-site beach access from this Hilton Head Island condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Beautifully Decorated Home with Lagoon a...

Every detail has been attended to in this immaculately kept and gorgeously decorated three bedroom, three and a half bathroom home! As you enter you're greeted by the home's open concept and vaulted ceilings in the living, dining and kitchen areas...

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

Hilton Head Tours & Activities

Six Hour Private Offshore Charter
Book online
$1,200.00

max_age: 99 group_size: For up to 6 guests description: Head out from Hilton Head Island for a private fishing charter aboard the Sweet Pea, a 29ft World Cat equipped with modern electronics and tackle. Captain John, a certified and experienced...

Discovery Lab Open House

Coastal Discovery Museum Hilton Head

description: Rates Suggested $5 donation per person (Ages 4+). Children must be accompanied by an adult. Everyone must have fun!! Duration 2 Hours (Drop in any time during Open House hours and stay as long as you'd like!) Discovery...

Crescent City Cocktails: A Taste of New Orleans

meeting_point: Hilton Head Distillery description: Step into the spirited traditions of New Orleans with this hands-on cocktail class celebrating the classics that made the Crescent City a cornerstone of cocktail culture. From refined sippers to...

One Day Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$49.99

description: Rate 1 Day Rental: $49.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 8 Hours

CCHH Kayak Tour

Outside

Book online
$35.00

meeting_point: Hilton Head Island, SC description: *Explore Hilton Head's waterways by kayak with an interpretive naturalist guide* --- Description Discover the Hilton Head tidal marsh by kayak… Bring the family kayaking through the tidal...

Gift Card

Drifter Excursions

description: Purchase the perfect gift: a gift card with a value of your choosing!

Daufuskie Island History and Artisans Excursion

Coastal Discovery Museum Hilton Head

Book online
$75.00 - $115.00

meeting_point: Shelter Cove Marina description: *Boat cruise from Hilton Head to Daufuskie Island* ___________________________________ Duration 4.5 Hours ___________________________________ About Tucked between Hilton Head Island and Savannah...

PB Outside Foundation Cruise

meeting_point: Palmetto Bluff description: The Outside Foundation and Palmetto Bluff are partnering to preserve the South Wilson Bluff, utilizing oyster shells recycled from Palmetto Bluff Club restaurants. To learn more about this program and other...

Private Sunset Cruise (Up to 34 Passengers)
Book online
$998.00 - $1,497.00

duration: 2 or 3 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 34 Passengers description: Enjoy the Sunset...

Beach Gear Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$40.00 - $200.00

duration: 14 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Bunch Bike - Family E-Bike Fun!

Pedego Electric Bikes Greenville

Book online
$109.00

duration: 6 to 8 Hours meeting_point: Pedego Electric Bikes Greenville. Located at Hampton Station - 1320 Hampton Ave Ext. STE 11A Greenville, SC 29601 description: Experience family fun like never before! ???? Experience the Thrill of...

One Week 2 Chairs and 1 Umbrella Package

Hilton Head Outfitters - Bike Rental

Book online
$79.99

description: The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

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