Hilton Head, SC Vacations

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Featured Vacation Rentals

Lovely villa with central AC, and easy b...

Bluff Villas 1733Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Harbor vistas and marina access are just some of the reasons why this Bluff Villas condo...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Island condo with beach access and balco...

Summary:Villamare 2319The Space:Appreciate all the amenities of home at this Palmetto Heaven. The fashonable furnishings and tasteful decor create a pleasant ambiance for a group of friends or the entire family. with a full kitchen, mealtimes will...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Lovely Condo with WiFi, Pool, On-Site Go...

Summary:St Andrews Common 1976The Space:With two bedrooms and two bathrooms, this second-level condo in the St. Andrews Common community is ready and waiting to be your next vacation hideaway! It offers access to a shared pool and on-site...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Oceanfront condo with pools, hot tubs, f...

Seacrest 2304Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your dream vacation spot on pretty Hilton Head Island! Our ideally-located, oceanfront...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
5 min walk to beach, ideal golf retreat,...

Summary:Greens 106The Space:Appreciate golf course vistas, beachy vibes, and a taste of the island lifestyle at this ideal condo just waiting for your next family vacation to Hilton Head. Step inside and you will immediately be greeted by the open...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Shipyard Condo next to pool, near tennis...

Summary:Tennismaster 302The Space:Welcome to your ideal coastal getaway in Hilton Head, SC! This gorgeous condo is just a fast 10-min. drive or bicycle ride from the sandy shores, making it the ideal base for your beach hideaway. With trendy...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Suns Out Floats Out Float-a-Palooza
Book online
$5.00 - $25.00

duration: 12pm-6pm max_age: 101 group_size: 200 description: Get ready for two full days of floating fun at Saluda Lake Landing during our Suns Out Floats Out Float-A-Palooza! Join us June 13–14 for DJs spinning all weekend long, cold drinks...

Private Food Tour

Food Tours Hilton Head

Book online
$695.00

description: Customize Your Tour! Duration 3 hours What's Included: - A private luxury SVU pickup for 6 - A knowledgeable tour guide About This tour is made especially for you. After you book the tour, our tour guide will contact you...

Bee Inspired: Celebrating World Bee Day in the Lowcountry

Coastal Discovery Museum Hilton Head

Book online
$10.00

duration: 1.5 cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: To mark...

Daufuskie Water Taxi
Book online
$15.00 - $45.00

duration: 20 minute shuttle • 4 or 8 hour golf cart rentals 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...

Eight Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$1,200.00

description: Duration 8 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, King Mackerel, Cobia, Triple Tail, Sharks! (Species Depend On Season, Tide & Weather) *This...

Guided Paddleboard Tour

Island Head- Hilton Head Harbor

Book online
$40.00

description: *Be one with the water* ___________________________________ Rates **Person:** $40 *Ages 12+* ___________________________________ Duration 1 hour ___________________________________ About Stand Up Paddleboarding focuses on...

Beach Gear Rental • Two Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $75.00

description: Everything you need for a fun and comfortable day at the beach! Duration 48 Hours About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later...

Private Party

Palmetto Axes

description: Get the joint all to Yourself! About *Ages 12+ • Up to 36 People* All the fun for you and as many people as the fire marshal will let in the place. Book 2 plus hours and save even more! - Bring in your own food - Maximum of 36...

Boomerang Private Charter Fishing
Book online
$540.00 - $640.00

meeting_point: Palmetto Bay Marina description: Rate **Three Hour** - $540 **Four Hour** - $630 About The Boomerang 2 is a comfortable 28 foot Parker center console that is powered by two brand new Suzuki outboards. We specialize in fun...

One Hour Sunset/Dolphin Cruise

Lowcountry Cowboy Fishing Charters

Book online
$40.00

duration: 1 hour meeting_point: Lowcountry Cowboy Fishing Charters description: Hilton Head has a ton of dolphins, and we wont come back to the dock until you see some! The sunsets are world class too! It's the perfect way to spend an hour enjoying...

Vineyard Tour

Victoria Valley Vineyards at Table Rock

Book online
$50.00

duration: Up to 2 Hours group_size: Max 4 People description: Join us for a tour of our vineyard and learn more about our small business! The vineyard tour consists of a 1- to 1.5-hour tour of the vines on our 47 acre property, where you’ll...

Four 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...

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