Hilton Head, SC Vacations

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Featured Vacation Rentals

Large Three Bedroom Villa Overlooking th...

You are going to appreciate staying in this very well kept three bedroom Inverness villa. This villa has been generously decorated throughout with the beach in mind. The entirely equipped kitchen with bespoke cabinetry has everything you will need...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Relaxing villa with pool, hot tub & tenn...

Island Club 4103Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'4103 Island Club is a gorgeously decorated, well-appointed villa located on the 1st floor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Oceanfront villa with WiFi, full kitchen...

Island Club 1203Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This alluring Island Club villa features fresh renovations for ultimate comfort, plus access...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Delightful dog-friendly beach condo with...

Ocean Breeze 14Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'For beachgoers seeking a cavernous, sunlit getaway while exploring everything Hilton Head has...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Newly Updated Villa – Short Walk to th...

The Villas at Tanglewood are professionally managed by Vacation Time of Hilton Head and offer the best booking experience when reserved directly through our website.Prime Location!!Welcome to Tanglewood 901!Feel the best of South Forest Beach in...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
2 Bed/2 Bath Villa North Shore Place Nea...

HILTON HEAD ISLAND. North Shore Place is THE spot for visitors who are looking to be in the center of activity in Hilton Head. Located next to Coligny Plaza, these deluxe villas are just steps away from some the Island’s best stores and eateries...

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

Hilton Head Tours & Activities

Daufuskie Island History & Artisans Excursion

meeting_point: Hilton Head Island, SC description: *Catch a glimpse into Lowcountry history!* --- Description This 4.5-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of...

Three Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$165.00 - $393.00

description: Enjoy miles and miles of scenic bike paths Duration 3 Weeks 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...

Paddle Splash Party

Hilton Head Island Recreation Association

Book online
$40.00 - $400.00

duration: 2 Hours meeting_point: Rowing and Sailing Center group_size: 15 description: Are you celebrating a birthday or want to schedule a group outing? Request a kayak, paddleboard or fishing party! Parties include a two-hour rental of...

Old Town Bluffton Farmers Market Cruise

Duration 4 Hours About Immerse yourself in the blissful charm of Old Town Bluffton, with this unforgettable excursion down the beautiful May River and get dropped off on the all new Calhoun Street Dock and Park in the heart of it all...

Tubing and Dolphin - 6 max

meeting_point: Hilton Head Island, SC description: Family Fun With Nature, Tubing and Exploring! --- Join us for a boating and tubing tour through the Lowcountry waters! Watch for birds and dolphin through the salt marsh ecosystem and get behind...

6-Seater Golf Cart Rentals

Mungeon Creek Golf Cart Rental

Book online
$89.62 - $962.26

duration: Day, Multi-Day, and Weekly Rentals! Contact us for long-term rentals. cancellation_summary: Full refund with 24 hours notice, rainy day gift card refund with less than 24 hours notice. meeting_point: 29 Haig Point Rd, Daufuskie Island, SC...

Exclusive Encounter

Bee City Zoo

Book online
$250.00 - $275.00

Duration 20 min encounter About Choose one of the ambassadors below: - Sloth - Capybara This encounter will include a photo with your ambassador, however no admission tickets are included with this encounter. Admission tickets to be purchased...

One Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$31.00 - $77.00

description: Enjoy miles and miles of scenic bike paths Duration 1 Day About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals - please select during...

Three Day Electric Bike Rental

duration: 3 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...

Private Fishing Charters

Performance Fishing Charters

Book online
$550.00 - $1,400.00

description: Hilton Head’s premiere fishing charter! Duration 3-8 Hour Rentals **Up to 4 people** Possibility for 5 with children About Located on Hilton Head Island, your charter will be guided by Captain John Cloyd, a USCG...

PB Private Freshwater Kayak Fishing

meeting_point: Palmetto Bluff, Bluffton description: *We have pioneered kayak fishing on the east coast!* ___________ About This is one of the fastest growing sports and is offered in the Inland Waterway Trails at Palmetto Bluff. The Hobie Pro...

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