Hilton Head, SC Vacations

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Featured Vacation Rentals

Island getaway by the ocean with balcony...

Summary:Windsor Court North 4504The Space:Warm sunshine and crashing waves await you at this home away from home. The expansive view from the balcony is beautiful, so savor your morning coffee and evening wine in the blissful ocean air! Take a...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Shipyard Plantation Villa at The Greens ...

Summary:Greens 170The Space:A enchanting island hideaway awaits at this two-bedroom villa, located in the exclusive gated community of Shipyard Plantation at The Greens. Inside, you'll find high-end furnishings and sweeping golf course vistas.Take a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Ocean view condo with shared pool steps ...

Summary:Captains Walk 448The Space:Make your next vacation one to remember in this inviting island home just steps from the sand. There is nothing better than stepping out to the balcony and feeling the sea breeze in your hair and the sun on your...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Beautiful Condominium with Ocean Views!

Appreciate a calming stay at this handsomely maintained Villamare condominium, thoughtfully designed with attention to detail throughout.The kitchen features stone countertops, stainless steel appliances, and ample cabinetry, making meal preparation...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Island gem with shared amenities, pond v...

Summary:Island Club 6205The Space:Take a break from it all and make the best memories at this second-floor condo in the relaxing, 27-acre Island Club of Hilton Head! Outside, appreciate fresh air and pond vistas from your furnished patio, while...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Updated getaway with pools, hot tub, clo...

Summary:Hilton Head Resort 1424The Space:NOTICE:Feel the best of Hilton Head Island in this refreshed apartment, where you can appreciate the island's pristine beaches, legendary golf courses, and countless sunshine. With cycling paths close by, you...

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

Hilton Head Tours & Activities

Guided Kayak Tour

H2O Sports

Book online
$45.00 - $90.00

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...

SC Pimento Cheese Festival- Pimento Cheese Competition

meeting_point: 2nd Annual Amateur Pimento Cheese Competition description: Does your pimento cheese have what it takes to win "South Carolina's Best Pimento Cheese" title? Registration **$25 per entry** - This fee includes entry into the...

Solaris - Palmetto Bluff Charter

duration: 2 Hours meeting_point: Palmetto Bluff group_size: Private Charter for up to 10 passengers description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **This private charter option accommodates 1-6...

Sunset Cruise

Reel Native Fishing Charters

Book online
$175.00

description: Enjoy the Sunset on the Water! Duration 2 hours About We're committed to providing a stress-free experience to both new and returning clients. More info Minors must be accompanied by adults

Three Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$60.00 - $300.00

description: Rent with us! Duration 21 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...

Three Hour Dolphin Strand Feeding Search

Hilton Head Island Tours

Book online
$375.00 - $395.00

description: *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** ...

First Friday Dinners

Victoria Valley Vineyards at Table Rock

Book online
$65.00 - $75.00

duration: 2.5 Hours group_size: Max 30 People description: Join us for an enchanting evening at our First Friday Dinner from 6 pm to 8:30 pm, as we celebrate friendship and good food in the picturesque setting of Victoria Valley Vineyards. This is...

Equestrian Lessons - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

Hilton Head Pedego Electric Bike Tour

duration: 2 hours meeting_point: Hilton Head Island, SC min_age: 16 pricing: $95 per person description: WHAT A GREAT DAY! HELLO FUN!!! what_is_included: There is no better way to experience Hilton Head than on a comfortable seat of a Pedego...

Bachelor/Bachelorette

Flip Flop Charters

Book online
$895.00

description: 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...

28 Day Rental

Island Life Rentals and Tours

Book online
$96.00 - $740.00

duration: 28 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...

Curator's Tour

Coastal Discovery Museum Hilton Head

description: Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg 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