Hilton Head, SC Vacations

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Featured Vacation Rentals

Conveniently located in Palmetto Dunes o...

The Queens Grant complex is conveniently located in Palmetto Dunes on the Robert Trent Jones Golf course in Hilton Head Island. Short walk to the beach, tennis and golf and a short bicycle ride to Shelter Cove Marina. This villa is on the ground...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront, Pool, Views, Luxury, Elevato...

31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its best. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication. Upon...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Updated, waterfront condo with amazing l...

Summary:Fairway Lane 102The Space:Located just a short distance from the beach in Sea Pines, this freshly refreshed condo is a warm and inviting, family-friendly hideaway boasting magnificant amenities both inside and out. Upgrades include new...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Family-Friendly Oasis. Beautifully Lands...

Welcome to Hilton Head Beach Villa 27!! Oceanview Villa with Pool Access and Family-Friendly Conveniences!Exciting News: Our Handsome New Swimming Pool is Now Open!This villa offers a prime oceanview location and direct access to a striking...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Beach resort condo with marsh-view balco...

Summary:HH Beach & Tennis 226CThe Space:Feel oceanside living just steps from the beach at this roomy, second-floor condo! Savor the sea breezes while watching for birds and other wildlife on your private balcony overlooking the tidal marsh. When...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Family Friendly Condo, outdoor indoor po...

Summary:Hilton Head Resort 1108The Space:NOTICE:Welcome to a gorgeously remodeled two-bedroom, two-bath condo located in the serene Hilton Head Resort. This calming getaway offers gorgeous balcony vistas overlooking the marsh, with the beach just a...

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

Hilton Head Tours & Activities

Lake Wylie Private Charters

Captain Jake's Guide Service

Book online
$250.00 - $600.00

duration: 3-8 hours meeting_point: Lake Wylie Boat Ramp-890 Nivens Landing Dr Fort Mill, SC 29708 description: Whether you're looking for an action-packed day of tubing and island hopping or a laid-back cruise to soak in the views, we’ve got you...

Donuts with Dolphins Aboard Dolphin Seafari

duration: 1.5 hours cancellation_summary: Full refund with 24 hours notice; call 843-785-2345 for cancellations or guest changes. group_size: Holds up to 20 people accessibility: Handicapped accessible pricing: * Adult - $45 * Child (12 and under) ...

Romance Package

Hilton Head Helicopter Tours

Book online
$100.00

pricing: $100 + Taxes/Fees description: Create unforgettable memories with your special someone aboard a private helicopter tour designed to ignite romance. Sip on complimentary champagne, savor a hand-selected box of chocolates, and let love take...

Ten Day Bike Rental

Wheelz of Hilton Head

Book online
$65.00 - $130.00

description: Ten Day Bike Rental Rates Duration 10 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Six Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$825.00 - $1,220.00

description: Golf Cart Rentals! Duration 6 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...

Day with The Native

Native Son Adventures 2

Book online
$365.00 - $1,260.00

duration: 2-8 hours cancellation_summary: Please let us know 48 hours in advance if anything causes you not to be able to go on your booked adventure. We will charge full price for not showing up for reservation without a 48 hour advanced notice...

Gift Cards

Carolina Hydrofly

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

Museum Closed Today

Coastal Discovery Museum Hilton Head

One Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$259.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

Shark Fishing Excursion

May River Excursions

Book online
$375.00 - $775.00

description: *Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* Rates are per private charter **2 Hours** - $350.00 **3 Hours** - $450.00 **4 Hours** - $550.00 **5 Hours** - $650.00 Each additional...

PB Private Outback Excursion - 6 passenger

meeting_point: Palmetto Bluff, Bluffton description: The Perfect Combination of Adventure and Fun! ___ Description This trip combines two of our most popular trips, The Dolphin Eco Tour and The Guided Kayak Tour, in an over the top remote...

Same Day E-Bike Rental • 9AM-4PM (up to 7 hours)

duration: up to 7 Hours meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to...

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