Hilton Head, SC Vacations

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Featured Vacation Rentals

Pet friendly Palmetto Dunes villa on the...

HILTON HEAD ISLAND. Wendover Dunes is a handsome oceanside villa complex that is just a short walk to the beach. Located next to the Barrington Enclave in Palmetto Dunes, these villas are delightfully decorated and equipped with all of the amenities...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Family-friendly condo w/ golf course vie...
4.6
(11)

Evian 208Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover Hilton Head from this second-story condo overlooking the golf course in Shipyard Plantation...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Waterfront resort on PR Sound!

Fall 2025 refresh! Kick back and relax with family and friends in this well appointed, chic villa. Carefully curated furnishings, linens, and linens to give you an fresh vacation experience! Far from the traditional rental space - pride of ownership...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
1st floor condo with patio, zero-entry p...

Shorewood 220Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your beachfront getaway in Hilton Head, SC! This first-floor condo offers painless...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Bright condo with beach access, pools, h...

Hilton Head Resort 3306Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in Hilton Head, SC! This striking 3rd-floor condo offers...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront condo with a washer/dryer, ce...

Shorewood 311Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'At this Hilton Head condo, you can take a dip in the seasonally-heated, shared pool, walk on the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Lake Keowee - Jet Ski Rental

Captain Cams Watersports

Book online
$275.00 - $350.00

duration: 4-7 Hours meeting_point: 757 Keowee Baptist Church Road Six Mile, SC 29682 min_age: 25 group_size: Up to 6 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight...

Shelling, Shark Tooth, & Dolphin Excursion
Book online
$45.00 - $525.00

___________________________________ Rates are based on 6ppl **2 Hours** - $300.00 **3 Hours** - $400.00 **4 Hours** - $475.00 *Can take a maximum of 12 people. Each additional person is $35* ___________________________________ About - Take...

Shark Fishing

Outside

Book online
$495.00 - $595.00

*Catch a shark and get out on the water at the same time!* --- There are few things more exciting than hooking a shark! Our three-hour evening shark fishing excursion includes boat, bait, tackle, USCG Captain, license, and an iced cooler. There...

Adopt-a-Dolphin

Coastal Discovery Museum

Book online
$50.00 - $100.00

About Sixty percent of all adoption money goes directly to the scientists who are studying these magnificent mammals and helps fund interns studying these dolphins, boat fuel, and supplies needed for the Marine Sensory and Neurobiology Lab in...

Private Sunset Cruise

Seaglass Charters LLC

Book online
$750.00

*Enjoy a Beautiful Sunset Cruise!* Duration 2 Hours About Seaglass Charters will provide bottled water and soda. You and your guests are welcome and encouraged to bring on board your own food and adult beverages (for those 21 and up) for...

Small Group Tasting

duration: 1 Hour min_age: 21 group_size: 6-10 people description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore...

13 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$51.00 - $355.00

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. Attendant will text you lock...

Family Fishing

Outside

Book online
$495.00 - $595.00

Family, Fishing, Fun! This 3-hour private Hilton Head Island fishing charter is great for families with kids and beginners! Catch and release only. Our family fishing charters include boat, bait, tackle, USCG Captain, license, and an iced cooler...

22' Hurricane Fun Deck

Hilton Head Island Boat Rentals

Book online
$325.00 - $1,525.00

About 22' Hurricane Deck Boat The Hurricane Deck Boat's "Fun Deck" Layout Up to 6 people Max Duration 2-8 Hours

Solaris - Happy Hour Cruise (up to 6 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book a luxurious charter aboard Solaris today! **Our private charters accommodate up to 6 passengers, ensuring an intimate and personalized experience for...

Bunny Eggspress

The South Carolina Railroad Museum

Book online
$17.00 - $140.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held the two Saturdays before Easter each year. Riders will board the train for a 3-mile trip to the Pumpkin Patch. We will stop the...

Glow in the Dark Splatter Session

Color Me Greenville

Book online
$50.00

duration: 30 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: $50 per person for Glow in the Dark Splatter Session. description: It’s your invite to light up the night...

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