Hilton Head, SC Vacations

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Featured Vacation Rentals

Family-friendly condo with lagoon views,...

Colonnade Club 181Our 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 Colonnade Club in Hilton Head, SC! Located within the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Dog-friendly condo with pool, central AC...

Moorings 43Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make your next Hilton Head Island vacation one to remember from the comfortable confines of this...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Exceptional Vacation Home with Community...

Calibogue Club 2604Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to sunlit serenity at Calibogue Club 2604, a handsomely appointed 2-bedroom, 2-bath...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious Condo with Beach Access, Shared...

Island Club 3304Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'During your stay at this bright rental villa, you can fish at the lagoon, swim at the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Charming condo with pool & balcony - ste...

Sea Side Villas I 108Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for a solo hideaway, a couple's escape, or even a holiday for a family of four...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Oceanfront, Dogs OK, Pool, Free Golf, El...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this impressive oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14

Hilton Head Tours & Activities

Fishing Charter - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

description: Duration 3 to 8 Hours Options About Near-Shore and Off-Shore Fishing. Ultra Stable, lots of shade, bean bags and Best of all Super Lucky! This experience is perfect for going after anything and possibly catching Bull-REDFISH...

Curator's Tour

Coastal Discovery Museum Hilton Head

description: Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg and...

Public Sailboat Charter

Charleston Sailboat Charters

Book online
$125.00 - $1,599.00

Duration 2.5 Hours About After a brief safety speech, we will shove off the dock and head into the scenic Charleston Harbor. As we raise the sails and turn the engine off, you'll immediately feel the relaxation set in and discover why the...

Sunset & Fireworks Dolphin Tour

Lowcountry Watersports

Book online
$15.00 - $59.99

duration: 2 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 1 max_age: 99 group_size: Maximum 48...

Black & Blue Fishing Charters

Black & Blue Charters

Book online
$425.00 - $1,700.00

description: Black & Blue Duration & Rates **Three Hour Fishing Charter** - $625.00 *Will catch mostly sharks* **Four Hour Fishing Charter** - $750.00 *Most popular for families* **Five Hour Fishing Charter** - $900.00 *Catch your...

Rosé Fireworks Sail

BC2 - Island Head

Book online
$19.99 - $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

Glow in the Dark Splatter Party! - Premium
Book online
$60.00 - $825.00

duration: 1.5 Hrs meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max description: It’s your invite to light up the night and vibe out with your crew! Experience the thrill of our glow-in-the-dark parties...

One Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

description: Electric Bike Rental Duration 7 Days 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 easier to get on and get going -- all...

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...

PB Outside Foundation Cruise

meeting_point: Palmetto Bluff description: The Outside Foundation and Palmetto Bluff are partnering to preserve the South Wilson Bluff, utilizing oyster shells recycled from Palmetto Bluff Club restaurants. To learn more about this program and other...

Valentines Nature Art for Seniors

Hilton Head Island Recreation Association

Book online
$25.00

duration: 1.5hrs meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: Maximum 20 people description: Come join Moore To Life and Island Rec Center for a holiday craft day. Give the gift of nature. Whether...

Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $900.00

description: This trip is great for kids or anyone who wants a little taste of Lowcountry fishing! **If you don't see a time on the calendar that works for you, text us at 843-422-5438 to see if we can accommodate you!** Duration 2 to 6...

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