Hilton Head, SC Vacations

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Featured Vacation Rentals

Cozy Hilton Head townhome with shared po...

Turtle Lane 4Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This townhouse-style vacation home furnishes you with a beautiful view of the close by golf...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Golf course-front condo w/ large deck & ...

Water Oak 27Our 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 appealing condo is located within the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunny & peaceful resort condo with golf,...

Golfmaster 206Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This beautiful, multi-level Golfmaster condo is the ideal spot to call home as you appreciate...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Enchanting beach/golf retreat with pool,...

Kingston Cove 27Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'**Please note that the TV on the outdoor patio is longer available which does not match photos...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Charming Townhome with Golf Course View,...

Summary:Shipmaster 901The Space:Welcome to an fantastic beach or golf hideaway located in Shipmaster Villas within Shipyard Plantation, a private gated community next to Hilton Head Island’s Coligny Beach! This End-Unit Townhome is strategically...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Welcoming villa with pool, beach access,...

Island House 138Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to the enchanting appeal of Hilton Head, SC, where white sandy beaches and acclaimed...

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

Hilton Head Tours & Activities

Private Sunset Cruise (Up to 34 Passengers)
Book online
$998.00 - $1,497.00

duration: 2 or 3 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 34 Passengers description: Enjoy the Sunset...

1 Hour Dolphin Tour

H2O Sports

Book online
$15.00 - $350.00

duration: 1 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...

Workshops

Coastal Discovery Museum Hilton Head

Book online
$5.00 - $35.00

duration: varies cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: Join us for a dynamic series of hands-on, creative workshops designed...

Private Kayak Date Tour

Crooked Creek Kayaks

Book online
$175.00

duration: 2 Hours group_size: Maximum 2 people description: Enjoy exclusive, private guided access into Jarvis Creek’s quiet, winding estuarine waterways — reserved solely for your group and led by your own personal guide. This tailored...

SCM Lowcountry Boil Dinner Cruise

duration: 2 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head pricing: Adults: $145 Children 10yr-2yr: $99 Under 2: $20 description: Set sail for an unforgettable evening on the water with Outside Hilton Head’s Lowcountry Boil Dinner Cruise...

Day Camp Sessions

Daufuskie Marsh Tacky Society

Book online
$425.00

description: Campers learn practical, natural horsemanship and riding skills! Duration 10 minutes About Youth (ages 7-17) are welcome to participate in one or more week long day camp sessions. Campers learn practical, natural horsemanship and...

One Day Fishing Rod Rental

Hilton Head Outfitters - Bike Rental

Book online
$25.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **This rental item includes ONLY the fishing pole, reel, and line.** This rental item DOES NOT include TACKLE or BAIT. Tackle and bait...

PVT Sunset Dolphin Cruise 6pk
Book online
$395.00 - $795.00

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane description: Looking for a private memorable evening on the water? Our Sunset Dolphin Cruise in Hilton Head is the perfect choice. This 90-minute private tour...

Rocky Land RC

Red Maple Event

Book online
$5.00

duration: 5 minutes meeting_point: Saluda Shoals Park min_age: 6 description: Customer will be able to drive a RC Crawler for 5 minutes on the Mobile Crawler Course what_is_included: Course Rules: -Stay in the course boundaries -No wreck less...

Blue Crab Discovery

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $90.00

min_age: 4 group_size: 12 description: *Explore where Atlantic Blue Crabs live, how they impact local communities, and why the Lowcountry enjoys and protects this food source!* ___________________________________ Duration 1.5...

Hilton Head Plantation Kayak Club May River Kayak Tour

meeting_point: Outside Palmetto Bluff

Daufuskie Trip

Flip Flop Charters

Book online
$725.00

description: Come explore the island! Duration 3 hours About Tucked between Hilton Head and Savannah is Daufuskie Island. With no bridges it is only accessible by boat. On the island are restaurants, golf courses, a distillery, and plenty of...

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