Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Panoramic view of the George Fazio Golf ...

Gorgeously decorated and open floor concept villa is conveniently located just a few steps to the community pool pavilion, Shelter Cove Harbour Marina, as well as the countless resort amenities. You will fall in appreciate with this coastal beach...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
Dreamy Island Gem W/ Golf Course View, P...

Heritage Villas 2229Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An memorable island vacation is never a bad idea especially when it comes to being perched...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Two-story villa with 3 pools, tennis & b...

Treetops 5501Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Scenically located among tropical palmettos and moss-draped woodlands, this two-story villa...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Inviting family-friendly condo with balc...

Village House 108Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Village House 108 is a enchanting condo located in the complex of The Village House in Port...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Oceanfront Condo with Shared Pool, Hot T...

Island Club 1101Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Kick back and relax in the striking amenities of this two-bedroom condo with peekaboo vistas...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Lush villa with on-site pool, WiFi, priv...

Forest Gardens 6Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the delightfully landscaped community of Forest Gardens Villas, this sun-kissed...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 5

Hilton Head Tours & Activities

Classic Splatter Party - Basic

Color Me Greenville

Book online
$35.00 - $495.00

duration: 1.5 Hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max description: Imagine a splatter paint party, a wild, colorful experience where you become artists by flinging, dripping, and splashing paint...

Carolina HydroFly Parties

Carolina Hydrofly

Book online
$800.00 - $1,600.00

Private Party About Enjoy a 4 or 8 Hour Group Lesson. Can have up to 8 people (Half day) & 16 people (Full day) in your party. - Includes 10 minutes of instruction time, fuel, life jacket, and helmet **What's Included** - Helmet - Life...

One Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$259.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a...

Twilight Guided Ghost Story Tour

Mungeon Creek Golf Cart Rental

Book online
$61.32 - $235.85

duration: 2 Hours group_size: Up to 20 guests description: Ride into the haunted history of Daufuskie Island with our Twilight Guided Ghost Story Tour! Join us for a chilling 2-hour adventure as the sun sets and shadows creep across the island. Your...

Romantic Sunset Cruise

Island Time Charters

Book online
$399.00

The most spectacular views and vivid colors! Duration 2 Hours About Come aboard for an enchanted, romantic cruise! Bring your favorite bottle of bubbly and we will provide the rest. This charter includes a sweet treat, fresh flowers, and...

Private Charter to Daufuskie

Daufuskie Difference

Book online
$350.00

Now Offering Private Boat Charters for Hilton Head Island. Get outside and enjoy a Dolphin Nature Cruise, Brunch or Lunch, or any of our other great Charter Options.

Valentine's Day Carriage Rides

Brice Herndon Draft Horse and Carriage Company

Book online
$100.00

A Fairytale Valentine's Day: Take Your Sweetheart on a Magical Carriage Ride. We will start from the north side of Union Point Park . Each ride is approximately 18 to 20 minutes long. The carriage will comfortably hold 4 adults and 2 small...

Explore Honey Horn

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

*Learn about Honey Horn's past and natural history!* ___________________________________ Duration 1 Hour and 30 Minutes ___________________________________ About Begin your Honey Horn experience with this guided tour around the museum’s...

Bike 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...

Indigo Tie Dye Party

Coastal Discovery Museum Hilton Head

Book online
$14.00 - $15.00

Come and join in the tie dyeing fun! Twist, twirl, tie, and dye with natural indigo dye. Why indigo dye? In 1739 Eliza Lucas Pinckney’s experiments with the indigo plant resulted in a very profitable cash crop for South Carolina. Enjoy a fun...

Outdoor Discovery Homeschool

Hilton Head Island Recreation Association

Book online
$40.00 - $800.00

duration: 1 Day per week for 1.5hrs meeting_point: Island Recreation Center min_age: 7 max_age: 14 group_size: Up to 14 Campers description: Outdoor Discovery Homeschool is a hands-on, nature-based learning program led by our Master Naturalist...

Paint the Pony - Montage Guests
Book online
$168.00

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

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