Hilton Head, SC Vacations

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Featured Vacation Rentals

Snowbird Friendly villa with Golf View, ...

Summary:Racquet Club Villas 2361The Space:Welcome to Racquet Club Villas 2361, a second-floor, condo tucked away in the Harbour Town Area of Sea Pines. This cavernous vacation rental offers golf course vistas and recent updates, creating a bright...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
3 bedroom/2 bathroom near ocean home wit...

This former artist's home and studio has been transformed into a excellent South Forest Beach, oceanside bungalow -- just a four-min. walk to the beach. It is the ideal, private setting for your casual family vacation. By day, recline in...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Beautiful Oceanfront Condo with Luxury F...

Come appreciate this one of a kind delightfully modernized unit. Everything from the walls in is new. The kitchen has been opened up and features a bespoke island, pendant lighting, shaker style cabinetry, stone countertops, high end appliances...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Beautiful Palmetto Dunes Villa- Lagoon V...

Summary:Queens Grant 762The Space:Welcome to your serene hideaway in Hilton Head, SC! This impressive three-bedroom, three-bathroom villa is located within the beautiful Palmetto Dunes' 11-mile lagoon system, offering a ideal blend of relaxation and...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Panoramic Intercoastal Waterway Views Fu...

This newly refreshed one bedroom and one bathroom villa is ideal for your next hideaway! The kitchen has been updated with quartz countertops and stainless steel appliances. Coming entirely-supplied, putting together meals is a breeze! The...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
Beautiful condo with pool, tennis, balco...

Summary:Courtside 56The Space:Ideally located in the beautiful Coligny Beach area, this home is within walking distance of the Atlantic Ocean and close by Coligny beach park! With gorgeous vistas of the pool, South Forest Beach just a half mile...

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

Hilton Head Tours & Activities

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Are you looking for the perfect Hilton Head family...

PB Private Outback Excursion - 6 passenger

meeting_point: Palmetto Bluff, Bluffton 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...

Four Hour Inshore/Nearshore Fishing Trip

Hilton Head Island Tours

Book online
$605.00 - $655.00

description: *Four Hour Inshore Fishing Trip* ___________________________________ Rates **Up to Four Guests** - $545.00 **Five Guests** - $575.00 **Six Guests** - $595.00 ***All ages welcome! | Maximum of 1200...

Brunch Under Sail

BC2 - Island Head

Book online
$19.99 - $89.00

duration: 2 Hours meeting_point: Broad Creek Marina 18 Simmons Rd. description: A Luxury Brunch Sailing Experience Step aboard our luxury catamaran for a truly elevated morning on the water. Brunch Under Sail is a two-hour sailing experience...

PB Palmetto Bluff Biking The Bluff

duration: 2 Hours meeting_point: Palmetto Bluff, Bluffton pricing: Starting at $70 per Guest description: *Palmetto Bluff is a bicyclists paradise!* Take a bike tour through Palmetto Bluff’s 20,000 acres, which include historic architecture...

2 Hour Beachcombing Dolphin Tour
Book online
$15.00 - $650.00

duration: 2 hour tour cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Guided Tours

Historic Mitchelville Freedom Park

Book online
$15.00

duration: Approximately 45min description: Step back in time and immerse yourself in the rich history of the first self-governed town of formerly enslaved people in America. At Historic Mitchelville Freedom Park, our guided tours offer visitors an...

SCM WAHHI Daufuskie Island History Tour

description: *Catch a glimpse into Lowcountry history!* --- Description This 4-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of the island. Visit several one-of-a-kind...

Riverside Lounge

Vintage View River Retreat

Book online
$5.00 - $125.00

duration: 5 Hours description: Our new Riverside Lounges take the traditional park picnic experience and elevate it to a premium, private basecamp on the banks of the Pacolet River. Each lounge is thoughtfully designed to provide a comfortable and...

Pony Rides - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Let your little ones experience the joy of horseback riding with our...

One Week Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$41.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold...

Two Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$40.00 - $200.00

description: Rent with us! Duration 14 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...

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