Hilton Head, SC Vacations

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Featured Vacation Rentals

2BR/2BA, Corner Villa w/ 3 Balconies, Fu...

Summary:Village House 104The Space:Village House 104 is a completely refreshed corner unit with 2BD/2BA located in Port Royal Village. Just a short walk to the beach, Westin, and mins. to golf. This exceptional villa offers 3 balconies to savor a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spectacular home located on the Robert T...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, sizable windows, skylights and striking vistas make this home one of the most inviting you will...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
This villa is close to everything that P...

Welcome to this roomy two-bedroom villa, charmingly located in the heart of Palmetto Dunes for simple access to the beach and various resort amenities! Ideal for families or friends, the villa is just steps from Centre Court’s pool complex and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beach + Pool Access: Colorful Hilton Hea...

Boogie down to the beach at this airy 2-bedroom, 2-bath condo on Hilton Head Island! Whether you’re looking to ideal your tan by a pool, prepare family-style meals in a completely equipped kitchen, or simply walk along impressive beaches this...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Minutes to the beach! Wonderful Sea Pine...

MINUTES TO THE BEACH! Wonderful three bedroom three bath home with private pool in Sea Pines within a short walking distance to the beach. Wonderful outdoor living space with lagoon and wooded vistas. Very private setting to relax and appreciate the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Beautiful 2 BR Villa - Hilton Head Marri...

Description ????Welcome to your Spectacular Two-Bedroom Garden View Villa at Marriott’s Monarch in sunny Hilton Head Island, South Carolina! This inviting getaway blends serene natural surroundings with thoughtful luxury, ideal for families...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

PB Private Stand Up Nature Walk
Book online
$95.00 - $325.00

description: *Stand-up paddleboarding is easy to learn, a fantastic workout, and lots of fun!* _____________ _____________ About Take a naturalist guided stand up paddle tour of the coastal salt marsh. An unbelievable perspective! ...

Three Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$485.00 - $740.00

description: Golf Cart Rentals! Duration 3 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

Sunset Dolphin Tour

Lowcountry Watersports

Book online
$10.00 - $49.99

duration: 1.5 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...

Two Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$35.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** These strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Fishing Charters

Hilton Head Inshore Charters

Book online
$425.00 - $1,200.00

description: Let's Adventure! About Inshore and nearshore fishing trips. Fun for the whole family. Targeting redfish, speckled trout, jack crevalle, tarpon, cobia, sharks, and more!

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Are you looking for the perfect Hilton Head family...

Cake Decorating

Color Me Greenville

Book online
$50.00 - $450.00

duration: 1 Hour 30 Minutes meeting_point: Color Me Greenville description: 1hr long party. Join us to decorate your own 5” cake! Booking includes unlimited buttercream, fondant, and sprinkles!

PB Private SUP Instruction
Book online
$75.00 - $325.00

meeting_point: Palmetto Bluff, Bluffton description: *Get on the water with one of our custom kayak tours & classes* Outside Palmetto Bluff has a professional staff of Instructors ready to help you enjoy the fun, fitness and beauty of the...

Beaufort Waterfront

Flip Flop Charters

Book online
$895.00 - $1,025.00

description: Explore Calhoun Street! Enjoy a Small Town Atmosphere! - 4 hours - 5 hours About Take a ride across the Port Royal Sound to the second oldest town in South Carolina. Downtown Beaufort is packed with history, art, shopping and...

Beach Bum

Hilton Head Helicopter Tours

Book online
$109.00

duration: 20 miles description: This helicopter tour follows Hilton Head’s most active stretch of beaches to Coligny Beach, the island’s popular beach park. Pilots keep the flight low along the shoreline for close-up views of surf and potential...

Homeschool Days

Coastal Discovery Museum Hilton Head

Book online
$2.00 - $30.00

duration: varies cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 description...

Outside DMC Partner Outing - Hilton Head Departure

description: *MUSIC | FOOD | FUN | & MORE* Outside DMC invites our partners to showcase Outside's OHANA & PAGE ISLAND! Join us for music, food, games, and more, and learn about the ultimate destination experience for your clients! Check-in will...

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