Hilton Head, SC Vacations

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Featured Vacation Rentals

133 Dune Ln, Oceanfront, Pool, Free Golf...

133 Dune Lane, Hilton Head Island is a 4-bedroom, 4-bath oceanfront home epitomizes casual beach living at its best. Wake up to beautiful vistas of the ocean from every room, including the kitchen, living room, dining room, and all four bedrooms...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Sunset Rentals | Forest Bch Villa 429

New furnishings bring both style and comfort to this 4th floor, 2 bedroom, 2 bath, 2 level villa located just across the street from the ocean in the Forest Beach Villas complex on Hilton Head Island, SC.Forest Beach Villa 429 is ideal for a safe...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
BEAUTY on The Sound!  Port Royal Hilton ...

Appreciate a different perspective on HHI... soak up the sun at the peaceful and sprawling Port Royal Sound, with your own private access to shell collecting, and sunny afternoons, in the pool or on the sand from this Sound-Side resort! While still...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Quiet Waterfront Condo with WiFi - Pools...

Island Club 2502Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Soak up the pretty vistas of the Atlantic Ocean from the balcony of this comfortable Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Golf course and lagoon views!

This striking four bedroom and four bathroom home is all one level, no stairs! The kitchen is well supplied with top-of-the-line stainless steel appliances and bespoke cabinetry. The living room features a 65” mounted flat screen TV, comfortable...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Private Oceanfront Home with Private Poo...

You'll appreciate this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting numerous sizable windows facing the oceanfront, this home provides oceanfront vistas from nearly every room! As you enter, you are...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14

Hilton Head Tours & Activities

Penguin Encounter

Bee City Zoo

Book online
$250.00 - $275.00

Duration 20 min encounter About Our ambassador is Penguin This encounter will include a photo with your ambassador, however no admission tickets are included with this encounter. Admission tickets to be purchased at $19.00 per person.

WAHHI Intro to Standup Paddleboarding

*Stand-Up Paddleboarding is easy to learn, a fantastic workout, and lots of fun!* --- Description Launch your Stand-Up Paddle Boarding career with this intro to SUP lesson in Hilton Head! This introductory program familiarizes you with...

Daufuskie Island to Hilton Head

Island Head - Broad Creek

Book online
$10.00 - $30.00

duration: 45 Minute Ferry Time cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Freeport Marina Daufuskie Island, SC description: Daufuskie Island Daily Return Trip We offer...

Kayaking & Coffee

Lowcountry Watersports

Book online
$49.00 - $98.00

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 min_age: 5 description: Let our experienced...

Baby Gear Rental Package • Two Days

Lowsea Bike, Beach and Baby Rental

Book online
$165.00 - $210.00

Don't pack it, Rent it! Affordable Baby Gear packages to meet your vacation needs! Duration 48 Hours About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Full Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$90.00 - $125.00

Single Kayak Full Day Rental: $99 ________________________________ Double Kayaks Full Day Rental: $150 _____ Duration 8 Hours

Banana Boat Rides

H2O Sports

Book online
$39.00

duration: 20 Minutes min_age: 6 description: Come enjoy an exhilarating ride aboard the 6 passenger, double-sided banana boat. Duration 20 Minutes About The journey begins in Harbour Town as you load up on the banana boat and steady yourself...

St. Patrick's Day Cruise

Island Head - Broad Creek

Book online
$99.00

duration: 10 Hours (2 Hour Boat Ride Each Way) 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 description: Enjoy St. Patricks Day in...

Glow in the Dark Splatter Session

Color Me Greenville

Book online
$50.00

duration: 30 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: $50 per person for Glow in the Dark Splatter Session. description: It’s your invite to light up the night...

Dolphins & Donuts

Lowcountry Watersports

Book online
$10.00 - $49.99

duration: 1.5 Hours cancellation_summary: Cancellations are allowed 48 hours prior to the scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 group_size: 48 description: Start your morning...

PB Intro to Stand Up Paddleboarding

*This introductory program will familiarize you with equipment, safety and paddle strokes. You'll be cruising down the creek in no time!* _____________ *(includes all equipment and Instructor/Guide)* Meeting Location - This activity will meet...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

See dolphins in their natural habitat! Duration 2 hours About The Lowcountry is home to several pods of Atlantic Bottlenose Dolphins. Join us for a 2 hour cruise to see them in their natural habitat and take in the beauty surrounding Hilton...

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