Hilton Head, SC Vacations

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Featured Vacation Rentals

Amazing Family-Friendly House w/ Private...

High Water 9Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An broad luxury home in Palmetto Dunes, High Water 9 features a single-level layout with seven...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 22
Splendid condo,  pool, full kitchen, & p...

Greens 153Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located within the exclusive Shipyard Plantation in Hilton Head, SC, The Greens condominiums offer a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
OPEN AND AIRY 3-BED 2-BATH ST. ANDREWS V...

St Andrews Common 1780Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'SEnjoy all the amenities of Palmetto Dunes Ocean Front Resort and Shelter Cove Harbour...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Comfortable Condo with Shared Pool, Hot ...

Island Club 3502Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This two-bedroom, two-bathroom condo will be sure to give you the comfort and amenities needed...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Third floor Penthouse with wonderful oce...

Seacrest is one of the most well known and ideally located complexes on the Island! Coligny Plaza, the Island’s original downtown is just across the street, with tons of stores and eateries just steps from your door. Also located on property are...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Beautiful Cndo at Port Royal Sound with ...

Spa On Port Royal Sound 3211Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this striking condo located in The Spa on Port Royal Sound, offering a...

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

Hilton Head Tours & Activities

Hilton Head Seafood Festival Daufuskie Island History Experience

description: Step Back in Time on Daufuskie Island Tucked between Hilton Head and the mainland, and accessible only by boat, Daufuskie Island is often described as “the other side of the river” — a hidden gem where time seems to stand still...

Bachelor/Bachelorette

Flip Flop Charters

Book online
$895.00

Explore Calhoun Street! Duration 4 hours About If you’re looking for a picturesque location to raise a glass and toast the happy couple, we’d love to help you celebrate! Waterfront bars are an excellent choice. With a stunning view of...

Shark Fishing Excursion

May River Excursions

Book online
$375.00 - $775.00

description: *Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* Rates are per private charter **2 Hours** - $350.00 **3 Hours** - $450.00 **4 Hours** - $550.00 **5 Hours** - $650.00 Each additional...

Island Explorer

Hilton Head Helicopter Tours

Book online
$149.00

This breath-taking tour travels over Hilton Head Island and all the surrounding beaches. Duration - **30 MILES** About - This is the perfect trip to see The Harbour Town Lighthouse, South Beach Marina, Shelter Cove Marina, Coligny Beach...

Bike Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

duration: 7 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: Confirmation will include your lock combination in addition to delivery and pick up...

Five Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 5 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...

Tubing and Dolphin - 16 max

meeting_point: Hilton Head Island description: This 3 hour excursion starts with our most popular Eco trip on pristine Broad Creek. From here We will cross the Calibogue sound into one of our beautiful tidal rivers. Once here we will inflate the...

1 Week Rental (Walk Up)

Island Life Rentals and Tours

Book online
$33.00 - $235.00

duration: 1 Week cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours...

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...

PB Outside Foundation Cruise

meeting_point: Palmetto Bluff description: The Outside Foundation and Palmetto Bluff are partnering to preserve the South Wilson Bluff, utilizing oyster shells recycled from Palmetto Bluff Club restaurants. To learn more about this program and other...

Advanced Wedge Play

Palmetto Dunes Golf Academy

Book online
$50.00

Make short approach shots the strongest part of your game! Duration & rates - 2 hours - $50 per student About When: Seasonal, by appointment only & course availability Where: TBD *Reservations are required*

PB Private Outback Excursion - 12 passenger

description: The Perfect Combination of Adventure and Fun! ___ Description This trip combines two of our most popular trips, The Dolphin Eco Tour and The Guided Kayak Tour, in an over the top remote location. A favorite of locals and visitors...

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