Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Hilton Head Island condo with water-view...

Seascape Villas 3205Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in a dreamy Hilton Head Island hideaway at this Seascape Villas condo. Perched...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Top-Floor Corner Villa with Pools, Tenni...

Hilton Head Resort 4401Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just a breathtaking boardwalk walk from the beach, this 3BR/2BA corner villa presents a...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Two bedroom Shipyard villa with golf vie...

The vistas from this enchanting two-bedroom two bath, second floor condo are the first thing you will notice when you walk through the doors. Overlooking a peaceful lagoon and golf course, this is the ideal place to spend your next golf hideaway or...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
French Country home on Golf Course with ...

Coastal CharmOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on the 1st Tee of the Clipper Course in Shipyard Plantation, this striking French Country...

  • Hilton Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Amenity rich condo with pools, tennis co...

Spa On Port Royal Sound 3313Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate beach hideaway at this impressive villa in Hilton Head, where...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Sunset Rentals | Evian 249

Escape to a Peaceful Retreat on Hilton Head IslandLooking for the ideal hideaway on Hilton Head Island? This elegantly refreshed 2-bedroom, 2-bathroom ground-floor villa in Evian at Shipyard offers the ideal combination of comfort, convenience, and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Horse Therapy Sessions

Daufuskie Marsh Tacky Society

Book online
$30.00

Groundwork sessions that focus on grooming, basic horse handling, and hand grazing. Duration 30 minutes About Experience therapeutic benefits through the healing power of the horse with groundwork sessions that focus on grooming, an...

2 Hour Fishing Charter

Awesome Adventure Charters

Book online
$410.00

Great Option for Families With Small Children or Novices Who Would Like to Give Charter Fishing a Shot! Duration 2 Hours About Whether going for that trophy fish, pursuing world-class tarpon in the ocean, or enjoying the scenery while fishing...

6 Hour Fishing Charter

Awesome Adventure Charters

Book online
$865.00

Allows You More Range and Time for a Well-Rounded Fishing Adventure! Duration 6 Hours About Whether going for that trophy fish, pursuing world-class tarpon in the ocean, or enjoying the scenery while fishing the salt marsh, you’re sure to...

Five Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

description: Five Day Rental Rates: - 16” Kids Beach Bike: $64.99 - 20” Kids Beach Bike $64.99 - 24” Youth Beach Bike: $64.99 - 26” Bike w/ Child Seat: $79.99 - 26” Mens Beach Bike: $64.99 - 26” Unisex Beach Bike: $64.99 - 12" Balance...

Twelve Day Electric Bike Rental

duration: 12 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...

Four Hour Private Inshore/Nearshore Charter

group_size: Up to 6 guests description: Experience inshore to nearshore fishing around Hilton Head Island aboard the 29ft World Cat "Sweet Pea." Fish for seasonal species such as cobia, bull reds, king mackerel, tarpon, and sharks while an...

4 Day Rental

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Nine Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$70.74 - $168.39

description: Enjoy miles and miles of scenic bike paths Duration 9 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

Donations

Daufuskie Island Gullah Heritage Society

Daufuskie Island Gullah Heritage Society is a non-profit 501(c)3 organization that is working to help restore the old Gullah homes, clean up and maintain Gullah cemeteries on Daufuskie Island. Many of the Gullah homes are deteriorating because...

Small Group Tasting

duration: 1 Hour min_age: 21 group_size: 6-10 people 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...

Two Day Fishing Rod Rental

Hilton Head Outfitters - Bike Rental

Book online
$35.99

description: Light Tackle Rod for use in the lagoon system

Distillery Experience

Best Of Hilton Head LLC

Book online
$35.00

description: Join us for the Island's Only Distillery Experience! Duration 4.5 Hours About We are providing the transportation and have orchestrated some great discounts and experiences for you to enjoy at the different...

Find your perfect Hilton Head

Fishing Charter

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