Hilton Head, SC Vacations

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Featured Vacation Rentals

Dog-friendly condo near Shelter Cove Mar...

Anchorage 7449Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a charming community near Shelter Cove Marina, this gorgeous hideaway is a sure bet...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious newly updated home, short walk ...

HILTON HEAD ISLAND. This four bedroom Palmetto Dunes home is a great choice for your next Hilton Head vacation. The roomy, sunken living room features a couch and 2 chairs around the huge TV with an additional sitting area overlooking the pool and...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
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
Fourth floor ocean front condo in Palmet...

These elegantly furnished 1, 2, 3, and 4-bedroom villas feature full kitchens, roomy living and dining areas, wet bars, cable TV, and huge master suites with sunken Jacuzzi tubs and separate showers. Appreciate dramatic vistas of the Atlantic ocean...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Beachfront condo with large furnished ba...

Beachside Tennis 1893Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor vistas of the ocean and Calibogue Sound from this bright and welcoming condo. While...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Sunlit Sea Escape with Al Fresco Dining,...

Greens 152Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to an action-packed vacation when you stay at this gorgeous condo on the island of...

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

Hilton Head Tours & Activities

Gullah Celebration Cruise

Vagabond Cruise

Book online
$90.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 80 passengers description: Join us for an extraordinary experience aboard the exquisite Spirit Of Harbour Town, as we embark on a captivating journey this year. Indulge in the...

Romance Package

Hilton Head Helicopter Tours

Book online
$100.00

pricing: $100 + Taxes/Fees description: Create unforgettable memories with your special someone aboard a private helicopter tour designed to ignite romance. Sip on complimentary champagne, savor a hand-selected box of chocolates, and let love take...

One Month Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$80.00 - $400.00

Rent with us! Duration 30 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and attachments

Earth Day Celebration

Hilton Head Island Recreation Association

duration: 2hrs meeting_point: Rowing and Sailing Center group_size: Up to 25 families description: Come join Moore To Life and Island Rec Center for an Earth Day Celebration! Have fun with the whole family while also helping our planet! Clean-up...

Lake Hartwell - Jet Ski Rental

Captain Cams Watersports

Book online
$275.00 - $350.00

duration: 4-7 Hours meeting_point: 470 Green Pond Rd, Anderson, SC 29625 min_age: 21 group_size: Up to 6 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight of the...

Fishing Trip

Reel Job Charter Fishing

Book online
$595.00 - $1,195.00

Fishing with Reel Job is sure to give you lasting memories! Rates All ages welcome aboard! - 4 Hour Charter - $595 - 5 Hour Charter - $695 - 6 Hour Charter - $795 - 8 Hour Charter - $1195 Please note, this price is a base price for 4 people...

Luxury Pontoon Rental with Fireworks Experience

Fireworks Pontoon Party Boat Rental and private VIP box for Harbourfest Fireworks Show! Captain your own adventure as you head out on a 2-hour self-guided cruise on a luxurious Bentley pontoon boat. Return to Shelter Cove Marina no later than 8...

Sunrise Cruise

Flip Flop Charters

Book online
$895.00

Limited Availability! Duration 2 hours About There are few things as beautiful as a Hilton Head sunrise. Every morning we’re greeted with the most brilliant colors as the sun makes its way over the horizon. Join us for a cruise to...

Three Hour Dolphin Strand Feeding Search

Hilton Head Island Tours

Book online
$375.00 - $395.00

*Dolphin Strand Feeding is a unique and exciting behavior developed by local Atlantic Bottlenose Dolphins!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages...

Sunrise Dolphin Tour

Lowcountry Watersports

Book online
$15.00 - $44.99

duration: 1.5 Hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 description: Experience the magic of the Lowcountry...

4 Hour Fishing Charter

Awesome Adventure Charters

Book online
$615.00

Our Most Popular Charter, Allowing Ample Time to Pursue Game Fish! Duration 4 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...

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