Hilton Head, SC Vacations

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Featured Vacation Rentals

Lovely, water-view townhouse with pool -...

Summary:Stoney Creek 272The Space:Stony Creek Villa in Sea Pines is a condo with a comfortable ambiance, making it ideal for a family hideaway or a casual vacation with friends. This townhouse overlooks a nature-filled marsh abounding with local...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Waterfront condo with seasonal pools, ho...

Island Club 141Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set your clocks to island time at this waterfront condo in the relaxing, 27-acre Island Club of...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Palatial Home Just a Short Walk to the B...

You'll be glad you and your family chose this huge five bedroom home with four full baths and two half-baths! The entire home has many upgrades and has been gorgeously decorated with comfort and the beach in mind. The kitchen is handsome and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Private condo with sound views, effortle...

Summary:Spa on Port Royal Sound 2219The Space:Settle down mere mins. from South Carolina's pristine beaches when you call this Spa on Port Royal Sound condo your next vacation destination! Located on a dead-end street, this private condo accepts you...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Spectacular home located on the Robert T...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, enormous windows, skylights and exceptional vistas make this home one of the most inviting you...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Coastal Condo with Pool, Hot Tub, Tennis...

Summary:Fiddlers Cove 12GThe Space:You'll find this completely refreshed, second floor condo and all its added perks just a half-mile from a striking Atlantic beach that will keep you coming back to Hilton Head. Guests of the Fiddler's Cove...

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

Hilton Head Tours & Activities

Birthday Parties and Private Events
Book online
$75.00 - $275.00

description: Give your child their best birthday yet! Rates - **Party Package Option A (includes 10 guests in the base price)** - $275 - **Party Package Option B (no guests included in the base price)** - $75 **Please contact us directly at...

Sweet Surprise Treat Tour- Feb 18 - March 4

meeting_point: Columbia, SC description: Ticket is valid: Saturday, February 18 - March 4 Receive 7 treats within 14 days Exchange your coupons (PDF will be sent via email and will need to be printed out) for a treat at each sweet shop. The...

Private Lesson with Doug Weaver

Palmetto Dunes Golf Academy

Book online
$160.00 - $800.00

description: About Doug Weaver, Director of the Palmetto Dunes Golf Academy Golf Digest South Carolina Top-Ten Instructor. Doug Weaver is a former PGA Tour Pro, US Open record holder and recent Lowcountry Golf Hall of Fame member. His weekly TV...

Hilton Head -> Daufuskie Island Daily Round Trip Ferry
Book online
$10.00 - $99.00

duration: 45 Minute Ferry Time 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: Hilton Head -> Daufuskie Island...

Three Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

description: Enjoy miles and miles of scenic bike paths Duration 3 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

Pontoon Boat Rental

Lowcountry Watersports

Book online
$270.00 - $625.00

duration: 2 Hour, 3 Hour, 4 Hour or 6 Hour 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 group_size: **Maximum of 10...

Private Sunset & Fireworks Cruise - 16p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

description: 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...

Gift Card

Wateree Marina

description: Purchase the perfect gift: a gift card with a value of your choosing!

Six Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

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...

Private Afternoon Sail and Dolphin watch on Knot The Office
Book online
$325.00 - $425.00

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 people accessibility: Limited Handicap accessibility, Please call us to ensure we can...

21 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$75.00 - $555.00

duration: 21 Days cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book...

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