Hilton Head, SC Vacations

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Featured Vacation Rentals

Spacious townhouse- close to beach, with...

Lyons 04Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the esteemed Port Royal Plantation, this impressive condo offers a prime location next to...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Family-Friendly Villa with Shared Pools ...

Island Club 6102Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bring along your friends and family members when you visit this comfortable Island Club villa...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Updated condo with patio, shared pool, a...

Stones Throw 43Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Blissful days of fun in the sun are made simple when you choose this alluring condo at Stones...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Updated, ground-floor island condo with ...

Fiddlers Cove 21BOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Island bliss awaits at this ground-floor villa at Fiddler's Cove Beach & Racquet Club...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Unique condo w/ bay view, balcony & spir...

Harbourside 7123Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to something special when you book a stay at this handsome condo in Hilton...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
OCEANFRONT!  Partial Ocean VIEW! Guarant...

***New serenity pool and main pool/hot tub/deck remodel is complete!POOL schedule: Heat 10/15 - 11/30 and 3/15 - 4/30Family pool; 7-10....sunrise to dusk Serenity pool: 7 - 10:30Outdoor pools closed from 11/30 - 3/15Indoor pool and Health club: ...

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

Hilton Head Tours & Activities

Classic Splatter Session

Color Me Greenville

Book online
$30.00

duration: 45 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 group_size: 6 Max description: 45 minutes of splatter painting on a 11x14 basic canvas board using our paints! Customization options available! 1 to...

Private Fireworks Cruise

Hilton Head Yacht Charter Company

Take to the water in style! Rates $5,000 for a private charter, up to 12 people Duration 4 hours About Hilton Head Yacht Charter at night is all about you. Imagine a luxury yacht, designed for ultimate entertainment, slipping through the...

2-Hour Sunset Sail

BC2 - Island Head

Book online
$19.99 - $99.00

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

Surfboard Rental

Forest Beach Surf & Cycle

Book online
$25.00 - $125.00

Rent with us! Duration 1 day, 3 day, or 1 week About Forest beach surf & cycle is your source for Hilton Head Island surf rentals!

Dolphin & Nature Tour

Dolphin and Nature Tours

Book online
$5.95 - $31.95

Rates - Adults (Ages 12 and up) - $31.95 - Child (Ages 2-11) - $16.95 - Wee One (Children under 2) - $5.95 ___________________________________ Duration 1.5 Hours ___________________________________ The best dolphin tour on Hilton Head...

Stand Up Paddle Board Rental

Forest Beach Surf & Cycle

Book online
$60.00 - $200.00

Rent with us! Duration 1 day, 3 day, or 1 week About Forest beach surf & cycle is your source for Hilton Head Island SUP rentals

Sweet Surprise Treat Tour- Feb 18 - March 4

Ticket is valid: Saturday, February 18 - March 4 Receive 7 treats within 14 days Exchange your coupons (PDF will be sent via email and will need to be printed out) for a treat at each sweet shop. The Midlands has some delicious dessert shops...

Dolphin Eco Tour

Captain Moto Adventures

Book online
$325.00

Duration 2 Hours About Not just your everyday dolphin tour. This is a private tour for the family. Learn about the local ego system and see dolphins. What to bring - BYOB - Sunglass - Sunscreen *No spray lotion* - Appropriate clothes...

Ricochet Private Charter Fishing
Book online
$440.00 - $540.00

Rate $440 for a two hour charter $540 for for a three hour charter About Join us aboard the brand new, Coast Guard inspected, 25 foot Ricochet, departing from Palmetto Bay Marina for an exciting 2 or 3 hour private shark fishing trip. The 2 hour...

Fishing for 6 or more

May River Excursions

Book online
$375.00 - $675.00

*Large fishing trip perfect for families and friends!* ___________________________________ Rates are based on 6ppl **2 Hours** - $375 **3 Hours** - $475 **4 Hours** - $575 *Can take a maximum of 12 people. Each additional person is...

Morning Half Day Sail Trip On Seas the Moment

Anchors Away Sailing Charters

Book online
$1,109.20 - $1,350.00

About Set sail aboard our monohull sailboat for a 4 hour customizable trip. Sail out to the ocean or stop and anchor and swim off the boat. The trip is up to you. All Half day Experiences includes Gratuity for the Captain and Crew of 18%. ...

Public Sailboat Charter

Charleston Sailboat Charters

Book online
$175.00

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...

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