Hilton Head, SC Vacations

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Featured Vacation Rentals

Bright condo with shared pools,  walk to...

Seascape Villas 3212Our 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 in Hilton Head, SC! This beautiful condo is charmingly...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Turtles & Tails - PET FRIENDLY - Palmett...

Savor the pristine golf & lagoon vistas from the back deck. The deck happens to overlook the 10th fairway on the Fazio course. This villa is so open and airy! It features two bedrooms and two bathrooms. The master bedroom offers a king sized bed...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
1400 sq ft of nothing but comfort and fu...

1400 sq ft of living space. The Villa is located in a gorgeously wooded area; that contains a pool and a pond with a fountain. It has 2 patios: to relax and appreciate the view. The upstairs patio can be accessed by both bedrooms so you can sit...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Hilton Head Island townhome with private...

Beckenham 116Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape the everyday and indulge in a dreamy golf-and-sea hideaway at this three-bedroom townhome...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
2-story condo with pool, beach, dog frie...

Hickory Cove 49Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on 2,000 acres of lush island landscapes, this elegant condo features prime access to...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Family Friendly Condo - Across From Isla...

Lyons 7Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to The Lyons, your ideal hideaway on Hilton Head Island, voted the #1 best island in the U.S...

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

Hilton Head Tours & Activities

Sunset Guided Kayak Tour

Island Head- Hilton Head Harbor

Book online
$49.00 - $95.00

description: *Paddle the Low Country!* ___________________________________ Rates **Kayak:** $49 **Tandem Kayak:** $95 *All Ages* ___________________________________ Duration 1 hour and 30 minutes ___________________________________ ...

Carmines Family Climb with Seafood Fest

Hilton Head Island Recreation Association

Book online
$5.00 - $20.00

duration: 1-3 Hours cancellation_summary: Cancellation Policy: To be eligible for a full refund, all cancellations must be made up to 24 hours before the scheduled start time. We can also move you to another session time if spots are...

Deck the Porch

Brice Herndon Draft Horse and Carriage Company

Book online
$15.00

Group Carriage Rides Climb aboard and stroll through our beautiful town as we harness in some of our Christmas magic. Travel along historic Hampton Street in Walterboro, known as the Front Porch of the Lowcountry and enjoy the twinkle of Christmas...

Stand Up Paddle Boarding Tour

Hilton Head Island Recreation Association

Book online
$40.00

duration: 1.5 hours meeting_point: Rowing and Sailing Center description: Your 1.5hr stand up paddle board trip will explore the marshes of Skull Creek. An educational Lowcountry experience learning and working with the tides, oysters, and...

Wine & Mead Tastings

Honey & Thistle

Book online
$25.00

duration: 1 Hour min_age: 21 description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore small-batch wines and...

Hilton Head Yacht Cruise

Salt Shaker Charter LLC

Book online
$3,750.00 - $6,600.00

duration: 4 - 8 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: Your Cruise, Completely Customized! At Salt Shaker Charter, every cruise is tailored to you. From intimate getaways to...

PRSF Lecture Series: White Shark Conservation

Port Royal Sound Foundation

Book online
$10.00

duration: 1 hour meeting_point: 310 Okatie Highway accessibility: Wheelchair accessible description: Dive into the fascinating world of white sharks as we explore cutting-edge research projects happening right here in the Northwest Atlantic. This...

Dolphin Nature Cruise

Island Time Charters

Book online
$325.00 - $399.00

Duration 2 or 3 Hour This is our most popular cruise for a reason! About This Dolphin and Nature Cruise takes you on the waters surrounding Hilton Head Island which inhabit hundreds of Atlantic Bottlenose Dolphins along with, osprey, great...

Private Afternoon Sail and 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 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we...

One Day Fishing Rod Rental

Hilton Head Outfitters - Bike Rental

Book online
$25.99

description: Light Tackle Rod for use in the lagoon system

Nightly Rental.  Premium 4 Passenger Electric Golf Cart. Pick up and drop off at rental address only

meeting_point: PICK UP AND DROP OFF AT RENTAL ADDRESS ONLY description: About 48 Volt Electric Golf Cart with 2023 Trojan Lead Acid Batteries.. Equipped with seat belts, anti lock brakes, extended top, LED headlights (high and low beam), turn...

Private Surf Instruction

Hilton Head Island Recreation Association

Book online
$60.00 - $150.00

duration: 1 hour & 15 minutes meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 group_size: up to 2 people description: Have a Private Learn to Surf experience in the safe and warm waters of Hilton Head Island! Our...

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