Hilton Head, SC Vacations

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Featured Vacation Rentals

Gorgeous waterfront home with lagoon vie...

Summary:8 Scaup Court - Whispering Palms at Tower BeachThe Space:Scenically located on the banks of a calming lagoon, this Hilton Head home is the ideal blend of serenity and convenience. Savor a short walk across the street to Tower Beach or walk...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Island oasis with balcony, beach access,...

Summary:Island Club 4106The Space:An memorable trip to Hilton Head awaits at this bright and ideally located condo sitting mere steps from the beach. Whether you have come to spend countless days on the warm sand or are dying to take a book out to...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Relaxing condo with pool, balcony

Summary:Springwood Villas 21The Space:This vacation rental in South Carolina is the quintessential spot for rest and relaxation! You'll be less than a mile from Coligny Beach Park, the ideal park for a gorgeous walk out on its dedicated walk path...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Comfortable getaway with pool, full kitc...

Beach Club BungalowOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in Hilton Head, SC! This beautiful condo offers a enchanting...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beautifully Updated with Ocean Views!

This condo has been charmingly refreshed throughout with a coastal feel and modern amenities. As you enter, the Kitchen is on your left and features all stainless steel appliances, granite countertops and comes completely-equipped to meet your...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Updated beach gem with ocean views, pool...

Shorewood 410Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You can access a shared swimming pool and hot tub when you stay at this fourth-floor Shorewood...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Lowcountry Lunch Cruise (Outside Dining)
Book online
$40.00 - $69.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Not wheelchair accessible description: ![Description of image](https://cdn.filestackcontent.com/bnLlDRzMSPaudj3mMT5x) Book Online and Skip the...

Heritage Garden Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

meeting_point: Meet in front of the Discovery House description: Duration 1 hour and 30 minutes ___________________________________ About All ages welcome but not a Family Friendly program. More geared towards adults but kids that are...

Quilting Workshop - A Fused Fabric Underwater Sea Collage

Coastal Discovery Museum Hilton Head

Book online
$35.00

duration: 3 hours cancellation_summary: Cancellation Policy: We will refund your payment (minus a $5 admin fee) if you cancel more than 72 hours before the event. We’re not able to offer refunds for cancellations made within 72 hours of the...

Sunset Cruise

Carolina Breeze Charters

Book online
$275.00 - $350.00

duration: 2 and 3 hour options meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Experience the magic of Hilton Head Island at the most breathtaking time of day—sunset—aboard...

Kayak Rentals (Please call if unsure about booking a Guided Tour versus a Kayak Rental)

description: Kayak unguided if you have kayaking experience. We will go over the area with you, tell you about the dolphins favorite spots to hang out and answer any questions that a you have before departure. Of course our guided tours are...

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...

A Taste of Daufuskie Island
Book online
$595.00 - $1,175.00

duration: 4 meeting_point: 1 Shelter Cove Lane, Hilton Head SC 29928 group_size: up to 6 pricing: $595/up to 6 guests description: Embark on an unforgettable Lowcountry adventure as you journey through the Carolina saltmarsh ecoststem to the...

13 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$95.99 - $191.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Guided Tour

Crooked Creek Kayaks

Book online
$45.00 - $70.00

duration: 2 Hours group_size: Up to 10 people description: Enjoy guided access into Jarvis Creek’s quiet, winding estuarine waterways This experience allows guests to journey in the most serene of settings, while learning about the island's...

Juneteenth Campfire Conversation & Sleepover with Joe McGill
Book online
$23.57 - $25.00

duration: 4 hours min_age: 10 max_age: 99 description: Gather around the campfire at Historic Mitchelville Freedom Park for an evening of meaningful conversation, shared history, and community connection led by Joe McGill of The Slave Dwelling...

Saint Helena Day Sail

Otter Sailing Adventures LLC

Book online
$350.00

description: Experience the awe-inspiring beauty of Low Country waterways and the Saint Helena Sound Duration 2.5 hours About Private Sailing Charter - Price Per Group (up to 6) Experience the awe-inspiring beauty of Low Country waterways...

Three Hour Private Inshore Charter

max_age: 99 group_size: Up to 6 guests description: Spend a day fishing Hilton Head Island waters with Captain John aboard the Sweet Pea, a 29 ft World Cat outfitted with modern electronics, tackle and an enclosed head for comfort. This inshore...

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