Hilton Head, SC Vacations

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Featured Vacation Rentals

2nd-floor snowbird-friendly condo with b...

Courtside 66Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for modest families and groups looking for a breezy and comfortable place to stay, this...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Exquisite oceanfront top-floor condo has...

Island Club 5503Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel spectacular unobstructed ocean vistas, morning sunrises, and handsome beach vistas from...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
2 bed/3 bath villa, spacious and updated...

Located directly on the George Fazio Championship golf course and the Palmetto Dunes lagoon system. Whether it’s a handsome golf view or serene lagoon you’re after, Fazio villas will deliver. These sizable villas are ideal for families and...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Redesigned Ground-Floor Villa with Pools...

Fiddlers Cove 11COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your ideal island hideaway awaits at this newly redesigned 2BR/2BA ground-floor villa at...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Palmetto Dunes Condo | Pool by the Golf ...

Turnberry Village 241Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located near the George Fazio golf course, this 2BR/2BA island getaway offers luxe...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Homey second-floor villa with admittance...

Evian 285Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate the best of Hilton Head at this roomy second-floor villa, located just steps from the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Creative Conversations: Paths to Publishing

We’re thrilled to invite you to our next workshop that promises to unlock the secrets of successfully becoming a published author. Join Meg Reid, the Publisher of Hub City Press, as she demystifies all aspects of publishing and the business of...

Flyboard 20 Minute

Carolina Hydrofly

Book online
$99.00

20 Minute Flyboard Pro Series Experience What's Included? 15 Min Flight Time. Includes 10 minutes of instruction time, fuel, life jacket, wetsuit, and helmet We advise everyone to arrive at least 30 minutes before your start time. If...

Round Trip Ferry Tickets | 9:30am - 3:30pm | Tuesday - Sunday

Round Trip Ferry Tickets to Daufuskie Island for 9:30am - 3:30pm | Tuesday - Sunday Ride the Daufuskie Island Ferry from Broad Creek Marina on Hilton Head Island to Daufuskie Island! • Depart from Broad Creek Marina on Hilton Head Island at...

Shared / Sunset Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$59.75

duration: 2 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

One Week - 4 Passenger Quad Stroller Wagon with Removable Canopy

PERFECT CARRIER FOR KIDS – Baby bags. Booster seats. Strollers. Sometimes, taking our little ones on the go with us is nearly impossible! Babies and toddlers alike love strolling around in the WONDERFOLD X4 Wagon, secured in a 5-point harness and...

Family Fishing

Hilton Head Island Recreation Association

Book online
$25.00

duration: 2 Hours meeting_point: Rowing and Sailing Center group_size: Up to 20 people description: Enjoy a night of fishing and education with your family and learn some pro tips from some of the Lowcountry's most sought-after Fishing Captains! In...

Outdoor After School

Hilton Head Island Recreation Association

Book online
$150.00 - $800.00

duration: 4 Weeks • 2 Days Per Week meeting_point: Island Recreation Center min_age: 7 max_age: 14 group_size: Up to 20 Campers description: This is an after-school program hosted by Outdoor Rec where kids ages 7-14 can receive assistance...

Beach Gear Rental • Five Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Everything you need for a fun and comfortable day at the beach! Duration 5 Days About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than 5PM. ...

The Shores of Asbury - Jet Ski Rental

Captain Cams Watersports

Book online
$90.00 - $325.00

duration: 1-7 Hours meeting_point: 1600 Asbury Park Road, Anderson, SC 29625 min_age: 25 group_size: Up to 8 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight of the...

Same Day E-Bike Rental • 9AM-4PM(up to 7 hours)
Book online
$30.00 - $55.00

Same Day: Electric Bike Rental Duration up to 7 Hours must be returned by 4:00pm same day About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Standard Step-Thru makes it...

SeaFood Fest Adventure Camp

Hilton Head Island Recreation Association

Book online
$100.00

duration: 2 days • 3 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 20 Campers description: Under the guidance of two Master Naturalists, children will explore the delicate balance of our...

Indigo Tie Dye Party

Coastal Discovery Museum Hilton Head

Book online
$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...

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