Hilton Head, SC Vacations

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Featured Vacation Rentals

1st Floor Condo with Pools,Hot tub, 100 ...

Island Club 1102Our 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 at The Island Club of Hilton Head! This impressive first-floor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Oceanfront Villa with Shared Pools, Hot ...

Summary:Villamare 1407The Space:Oceanfront villa just refreshed, steps from the beach, sizable pool, and hot tub!Pristine, comfortable condo lets you go to sleep to the sound of the waves. Scenic ocean vistas from every room and balcony. This...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Wonderfully Updated Three Bed Four Bath ...

This gorgeous completely remodeled three-bedroom, four-bathroom villa is ideal for families or golf, tennis, and pickleball groups. The beach can be conveniently accessed by a short walk or by calling the seasonal, on-call Palmetto Dunes Buggy. The...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Golf-course view condo with central AC, ...

Summary:Greens 125The Space:From mornings on the links to leisurely beach afternoons, this freshly refreshed condo puts you right at the center of vacation fun. Make plans for the day while you sip morning coffee on your patio overlooking the golf...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Very Nice Ranch-Style Home Located on 11...

You will be impressed by this freshly remodeled home within Palmetto Dunes Resort! The Kitchen features Granite countertops, stainless steel appliances, and bespoke cabinetry. The Kitchen will be completely equipped with all the amenities of home...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Third floor Penthouse with wonderful oce...

Seacrest is one of the most well known and ideally located complexes on the Island! Coligny Plaza, the Island’s original downtown is just across the street, with tons of stores and eateries just steps from your door. Also located on property are...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

SC Pimento Cheese Festival- Vendor
Book online
$30.00 - $125.00

duration: 8 hours meeting_point: 6071 St Andrews Rd, Columbia, SC 29212 description: With over 2,500 in attendance in our 1st SC Pimento Cheese Fest last year, we believe this year will be bigger and better! Promote your business in front of the...

Southbay Pontoon

Santee Boat Rentals

Book online
$350.00 - $500.00

description: Book our Southbay Pontoon today! Duration: - Full Day (8 Hours) - Half Day (4 Hours) About: The Southbay pontoon boat is a 20ft pontoon boat with a 90hp Suzuki to get you around the lake. With that being said the 90hp has...

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

description: Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy...

Lighthouse Admission

Harbour Town Lighthouse

Book online
$8.00

description: Climb Through Time & Explore The History of the Island! Duration All Day Admission Open everyday 10 a.m. to sundown. About Climb 114 steps as you travel through Hilton Head Island history. Explore the Island’s rich history...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

description: See dolphins in their natural habitat! Duration 2 hours About The Lowcountry is home to several pods of Atlantic Bottlenose Dolphins. Join us for a 2 hour cruise to see them in their natural habitat and take in the beauty...

Private Morning Sail / dolphin watch on Seas The Moment - newest vessel

duration: 2 Hours cancellation_summary: 72 hour free cancellation meeting_point: 1 Waterway Lane, Hilton Head Island SC 29926 max_age: 90 group_size: Maximum of up to 12 people accessibility: Limited Handicap accessibility, Please call us to...

Private Dolphin Encounter - Two Hour

Island Life Rentals and Tours

Book online
$45.00 - $540.00

duration: 2 Hours group_size: 12 - 14 Max description: Every trip is a unique experience. Dolphins abound in the Hilton Head waters, and you'll enjoy the thrill of seeing them up close aboard Island Life's safe, comfortable boats. Our experienced...

Two Day Electric Bike Rental
Book online
$120.00

duration: 2 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...

One Week Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$225.99 - $299.99

description: Single Kayak Full Day Rental: $225.99 ________________________________ Double Kayaks Full Day Rental: $299.99

General Admission

Bee City Zoo

Book online
$17.00 - $19.00

description: Come explore our honeybee farm, interactive zoo, gift shop, cafe, nature trail, & nature center! Duration General Admission tickets are good for an *entire* day at the zoo! Please note you can always purchase tickets the day of...

America 250 Hilton Head History Cruise
Book online
$24.95 - $44.95

duration: 1.5 Hours cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 group_size: any size group accessibility: Yes description: Celebrate America’s 250th Anniversary with an...

Corporate Parties & Team Building

Color Me Greenville

Book online
$50.00 - $400.00

duration: 1.5 Hours cancellation_summary: 7 Days meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: 1.5 hours active painting for groups of people. Includes a 11”x14” premium canvas for each attendant plus a 18”x24”...

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