Hilton Head, SC Vacations

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Featured Vacation Rentals

Wonderfully Updated Two Bedroom Villa Cl...

You'll be glad you chose this fabulous two bedroom villa with its freshly refreshed kitchen, floor, beds, linens and furnishings! The floor has been updated throughout the entire villa. The beds in both the primary and guest bedrooms are new along...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Convenient Location plus Golf Course Vie...

This Hilton Head handsome two bedroom, two bath plus additional twin room villa has amazing vistas of the George Fazio golf course! The kitchen is completely equipped featuring new stainless steel appliances and granite countertops. The pass-through...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Fully Updated Two Bedroom Condominium in...

You'll adore this two bedroom condominium located in Villamare within Palmetto Dunes Oceanfront Resort! The kitchen is generously refreshed with stainless steel appliances and quartz countertops. The kitchen will be entirely-outfitted to meet your...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Coastal condo with ocean views, pools, t...

Island Club 1502Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the best of Hilton Head Island at this family-friendly condo located in the esteemed...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Sunset Rentals | Evian 164

This handsomely refreshed 3 bedroom and 3 bath, townhouse villa will not let you down. To the immediate left of the entry door is a bedroom with a twin- size bed along with a duobunk bed (twin-size on top and full-size on bottom), a TV, a walk-in...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Expansive Private Oceanfront Home with V...

Fall in adore with this broad oceanfront home located on the Atlantic Ocean in handsome Palmetto Dunes Oceanfront Resort! As you enter you are welcomed by a grandiose staircase and wood floors leading to the kitchen, dining and living areas. The...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Solaris - Sunset Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for 7 to 10 passengers description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **This private charter option accommodates...

Seasonal Fireworks Cruise

Flip Flop Charters

Book online
$775.00

Watch fireworks at Shelter Cove! Duration 3 hours About From June to August we offer a weekly cruise to watch the fireworks at Shelter Cove. You’ll have a front row seat to see the magic aboard! This three hour cruise is only on Tuesdays in...

2 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$18.00 - $100.00

duration: 2 Days meeting_point: Hilton Head Island, SC description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day...

Private Sunset & Fireworks Cruise - 16p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Pluff Mudder Summer Camp

Port Royal Sound Foundation

Book online
$445.00

duration: Monday-Friday cancellation_summary: Due to limited space and high demand for our Pluff Mudder Summer Camps, all payments are non-refundable. Please let us know as soon as possible if you have to cancel your reservation so we can fill your...

Five Day Electric Bike Rental
Book online
$250.00

duration: 5 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...

Plant Native!

Port Royal Sound Foundation

Book online
$15.00

duration: 1 hour min_age: 5 description: This interactive one-hour workshop introduces participants to native plants, their ecological benefits, and practical seed-planting techniques. Guests will learn how to select and plant seeds, care for young...

Explore Honey Horn

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *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...

PB Private Outback Excursion - 6 passenger

meeting_point: Palmetto Bluff, Bluffton description: The Perfect Combination of Adventure and Fun! ___ Description This trip combines two of our most popular trips, The Dolphin Eco Tour and The Guided Kayak Tour, in an over the top remote...

Flyboard 20 Minute

Carolina Hydrofly

Book online
$99.00

description: 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...

Sweetgrass Basket 3-Day Workshop

Coastal Discovery Museum Hilton Head

Book online
$425.00

meeting_point: Coastal Discovery Museum description: March 19, 20, 21, 2025 from 9:30-12:30 on each date. World-famous but with origins right here in the Lowcountry, the Sweetgrass basket is one of the region’s best known art forms and cultural...

C - PB Nature Walk

meeting_point: Palmetto Bluff, Bluffton description: MAY RIVER WALK AT THE BLUFF Palmetto Bluff is a nature lovers paradise. This interpretive tour will take a loop route that will mix forested paths as well as paths along the May River all at...

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