Hilton Head, SC Vacations

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Featured Vacation Rentals

Stunning oceanfront villa with WiFi, poo...

Windsor Court South 3108Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'3108 Windsor is a striking 3 bedroom, 3 bath oceanfront villa located in Palmetto...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Beautifully Updated Three Bedroom Villa ...

This attractively modernized villa has been completely refreshed from the walls in, including brand new HVAC systems, creating a modern and extravagant coastal getaway. The kitchen is really a standout, featuring entirely bespoke cabinetry, GE...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Wonderfully Updated Three Bedroom Villa ...

Welcome to your Hilton Head Island hideaway! This delightfully refreshed 3-bedroom, 4-bath villa is in the heart of Palmetto Dunes in the Water Oak community. It is just 25 steps from the complex pool and a short walk or bicycle ride to the beach...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 7
Sunset Rentals | Fazio 34

34 Fazio is a roomy, handsomely remodeled 4 bedroom, 3-bath, end unit townhouse in the impressive Palmetto Dunes Resort on Hilton Head Island.Upon entering this cavernous Palmetto Dunes villa you will be greeted by the tile floor entry which leads...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Townhome style with lagoon Views!

You'll be glad you chose this sizable villa with its many updates and painless walk to the beach! Updates include new floor throughout, beach-modern furnishings and paint along with a completely refreshed primary bathroom!The primary bedroom is...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
5 min walk to beach, ideal golf retreat,...

Greens 106Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor golf course vistas, beachy vibes, and a taste of the island lifestyle at this ideal condo just...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Dolphin Tour

Lowcountry Watersports

Book online
$10.00 - $39.99

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: Maximum 48 people description: Experience...

Luxury Sunset Cruise

BC2 - Island Head

Book online
$1,200.00 - $1,600.00

duration: 2-6 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Santa’s Twilight Express

The South Carolina Railroad Museum

Book online
$27.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual twilight holiday ride. Santa walks through the train and comes to you—no lines! As we travel down the tracks, the...

2 Week Rental (Walk Up)

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours self pick up and drop off available...

Bachelorette Booze Cruise Party

Unwritten Charters LLC

Book online
$1,200.00

Enjoy a Private Cruise for that special event! Duration 4 Hours About Is the stress of planning your big day getting to you? Why not get together with all of your friends on a private cruise around Charleston Harbor on one of our luxury...

PB Private Daufuskie Island Tour - 12 passenger

*Catch a glimpse into a fascinating chapter of Lowcountry history* --- Description Tucked between Hilton Head Island and Savannah, and accessible only by boat, Daufuskie Island is a real gem. This trip provides a glimpse into a fascinating...

Private / Dolphins, Sharks & Shells!

Dolphin Discoveries Hilton Head

Book online
$475.00 - $1,065.00

duration: 3 to 6 Hours cancellation_summary: 48 Hours meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. max_age: 1000 group_size: 6 accessibility: Two, 8" steps down into boat. We are here to help. pricing: All Dolphin...

Ohana Sunset Dolphin Cruise
Book online
$45.00 - $2,500.00

Explore the marsh and enjoy the view of the incredible Lowcountry sunset! --- Join us for this 90-minute tour to learn about the salt marsh and search for local dolphins aboard the luxury catamaran, Ohana! Guests are welcome to bring snacks and...

Solaris - Happy Hour Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Book a luxurious charter aboard Solaris today! **Our private charters accommodate up to 10 passengers, ensuring an intimate and personalized...

Six Hour Inshore Fishing

Happy Dog Charters

Book online
$700.00

Come aboard and let's go fishing! Duration 6 Hours About This is a trip where we will cover it all, from catching bait to several different spots. We will be moving and finding fish several times unless the bite is absolute...

Director's Walk

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $25.00

*Visit Honey Horn with the Museum's Director.* ___________________________________ Duration 1.5 Hours ___________________________________ About Walk the shell path and Nan Lloyd Trail with the Museum director and discover some of the...

Beach Gear Rental • Four Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Everything you need for a fun and comfortable day at the beach! Duration 4 Days 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 than 5PM. ...

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