Hilton Head, SC Vacations

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Featured Vacation Rentals

Newly remodeled dog-friendly island sanc...

Golfmaster 501Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get away from it all and soak up some island sun when you stay at Golfmaster 501. This handsome...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Perfect condo right by the beach w/ shar...

Breakers 128Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Parlor on your deck and appreciate the sea breeze in this haven on the beach! Take a moment and...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Lovely 2 bedroom townhome in Shipyard ju...
4.0
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Located in Shipyard Plantation, this delightful town home is just a short walk to the beach!The floor plan of this special 2 bedroom, 2.5 bath town home has been refreshed to open up the kitchen, dining and living areas on the 1st floor, providing a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Wonderful sun-filled retreat w/ generous...

Harbour Master 201Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This grand Hilton Head condo, close to beaches and nightlife, is ideal for any couple’s...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Lovely Two Bedroom Condominium with Ocea...

This two bedroom Hampton Place condominium has been decorated with the utmost care. New furnishings abound in this modern beach-themed condominium! The kitchen is fashonable with its stainless steel appliances and granite countertop while being...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Beautiful Oceanfront Condo with Luxury F...

Come appreciate this one of a kind handsomely 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 and...

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

Hilton Head Tours & Activities

Morning Half Day Sail Trip On Knot The Office Sailboat

About Set sail aboard our monohull sailboat for a 4 hour customizable trip. Sail out to the ocean or stop and anchor and swim off the boat. The trip is up to you. All Half day Experiences includes Gratuity for the Captain and Crew of 18%. ...

Small Group Tasting

duration: 1 Hour min_age: 21 group_size: 6-10 people description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore...

A.C.E. Basin & Monkey Island Tour

Beaufort Dolphin Adventures

Book online
$353.77

duration: 2 Hours cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances...

Guided Paddleboard Tour

duration: 1 hour tour cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! description: H2O Sports is thrilled...

Bike Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $80.00

duration: 1 Day cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental drop...

Shared / Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$49.75

duration: 1.75 to 2 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina group_size: Max 6 accessibility: Boats take 2 steps from dock to deck. We are here to help. pricing: $49.75 per seat This...

Private Lesson with Sean Ritter

Palmetto Dunes Golf Academy

Book online
$90.00 - $450.00

About Sean Ritter Sean Ritter graduated from the Professional Golfers Career College in Bluffton, SC with honors and is originally from Charlotte, NC. After his graduation, Sean was further mentored and tutored under the award-winning Palmetto...

Two Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$345.00 - $525.00

Golf Cart Rentals! Duration 2 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online due to South...

Learn to Row

Hilton Head Island Recreation Association

Book online
$40.00

duration: 2 days • 3 hours per Day meeting_point: Rowing and Sailing Center min_age: 11 max_age: 18 group_size: Up to 10 Campers description: Learn the basics of rowing. The camp utilizes 1-4 person shells (boats) and will teach participants...

Old Town Bluffton Inn May River Discovery Cruise

duration: 90 Minutes meeting_point: 110 Calhoun Street, Calhoun Street Dock group_size: Maximum 6 people pricing: . description: Take a cruise on the May River in an authentic South Carolina skiff boat. Your guide is a master captain and an expert...

Paddle Splash Party

Hilton Head Island Recreation Association

Book online
$40.00 - $400.00

duration: 2 Hours meeting_point: Rowing and Sailing Center group_size: 15 description: Are you celebrating a birthday or want to schedule a group outing? Request a kayak, paddleboard or fishing party! Parties include a two-hour rental of...

SC Pimento Cheese Festival- Vendor
Book online
$30.00 - $125.00

duration: 8 hours meeting_point: 6071 St Andrews Rd, Columbia, SC 29212 description: With over 2,500 in attendance in our 1st SC Pimento Cheese Fest last year, we believe this year will be bigger and better! Promote your business in front of the...

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