Hilton Head, SC Vacations

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Featured Vacation Rentals

Queen’s Grant Condo w/5 pools, tennis ...

Queens Grant 771Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With five swimming pools, three golf courses, an award-winning tennis center, and miles of...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Oceanfront beach villa in Palmetto Dunes

**WINDOW AND DOOR REPLACEMENT PROJECT TENTATIVELY SCHEDULED 9/15-4/10/26 AND IS SUBJECT TO CHANGE. SCAFFOLDING WILL BE UP DURING THIS TIME. Due to the nature and scope of the work there is a possibility that your accommodations may be affected. If...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2 Beach Villa Steps From the Sand!

This three bedroom Palmetto Dunes Beach Villa is located directly on the sand and will surely meet all of your expectations for the ideal island vacation. The living room was freshly refreshed with high-end designer furnishings and accents and was...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
The Pool Is At Your Doorstep!

Many updates have been made to this huge poolfront villa. The Kitchen has all the amenities of home and comes completely-equipped to meet your family's cooking needs. The Dining Area has seating for eight and is located between the living and...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Bright & Beachy Dog-Friendly Villa w/ Fa...

Tennismaster 1102Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note the Tennismaster pool is closed as of 9/25/2025. Renovations will begin...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Oceanfront Views, Recently Updated, Thre...

This third floor handsome condominium, within the Captain's Walk community, has direct oceanfront vistas that will not disappoint.The kitchen to the left as you enter, comes entirely-outfitted to meet all of your needs during your calming stay...

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

Hilton Head Tours & Activities

Fireworks Cruise

BC2 - Island Head

Book online
$89.00

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Ten Day Electric Bike Rental
Book online
$400.00

duration: 10 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...

Three Hour Shark Fishing Excursion

Hilton Head Island Tours

Book online
$445.00 - $495.00

*Shark Fishing Trip! * ___________________________________ Rates **Up to Four Guests** - $445.00 **Five Guests** - $475.00 **Six Guests** - $495.00 ***All ages welcome! | Maximum of 1200 lbs*** ___________________________________ About your...

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...

2-hour Afternoon Sail and dolphin watch Seas The Moment - Our newest boat

*Afternoon Sail* Generally a breezy afternoon leading to some of our most exciting sailing all day. Come and experience true sailing without running the motor. Take the helm and help with handling sails if you desire, but either way, kick back...

PB Palmetto Bluff Biking The Bluff

duration: 2 Hours meeting_point: Palmetto Bluff, Bluffton pricing: Starting at $70 per Guest description: *Palmetto Bluff is a bicyclists paradise!* Take a bike tour through Palmetto Bluff’s 20,000 acres, which include historic architecture...

Oktoberfest at The Landing

duration: 12pm-8pm max_age: 101 group_size: 300 description: Celebrate Oktoberfest lakeside every weekend at Saluda Lake Landing! Join us every Saturday and Sunday from September 20 through October 19, from 12 PM to 8 PM, for a fun and festive...

One Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$60.00

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 small motor engages and gives you a boost, so you can zip through...

Two Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$380.00

Duration 2 Hours ___________________________________ About Learn about fishing, catch sharks and other species and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you will catch....

One Week Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$250.00 - $350.00

Single Kayak Full Day Rental: $275 ________________________________ Double Kayaks Full Day Rental: $375

Historic River Excursion

May River Excursions

Book online
$40.00 - $50.00

*Learn more about Bluffton through our scenic trip!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ Duration 1.5...

Hack, Snack and Roadie Ride

Daufuskie Marsh Tacky Society

Book online
$450.00

Duration 3.5 Hours Please Note This is experience is designed for novice or better riders who are comfortable with longer hours in the saddle and are able to independently mount/dismount their horses easily, this culinary and riding adventure...

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