Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Sunny & peaceful resort with golf, pool,...

Summary:Golfmaster 206The Space:This gorgeous and modern multi-level Golfmaster condo is an ideal home base for appreciating the best of Hilton Head—whether you’re here for golf, the beach, or great local dining.Take advantage of resort-style...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Penthouse living at Shelter Cove Marina ...

Summary:Harbourside PenthouseThe Space:Feel the luxury of penthouse living at this all-suite 3BR/3BA condo with a covered balcony overlooking the harbor. Your fourth-floor hideaway features a gorgeous kitchen, spiral staircase, and a lavish master...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Newly-renovated  getaway in North Forest...

Summary:Breakers 311The Space:This direct oceanfront condo offers the absolute best vistas on the Island! This home features a bright and inviting living area with a enormous, flat screen TV, a full, well-equipped kitchen with stainless steel...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Single level Sea Pines home with a hot t...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.Single-level home with 3 bedrooms and a short walk to the beach! Savor close access to the beach in this entirely modernized coastal chic ranch home with a hot...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beach Villa:Close to all the action! Bea...

Fantastic location - walk to Coligny Beach and/or the Coligny stores and eateries.Peaceful, enclosed courtyard with a huge pool and sunbathing areas.Dine out or grille your dinner on private patio - gas grille and outdoor dining table.Villa has a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Oceanfront Views, Recently Updated, Thre...

This third floor striking condominium, within the Captain's Walk community, has direct oceanfront vistas that will not disappoint.The kitchen to the left as you enter, comes completely-outfitted to meet all of your needs during your calming stay...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

One Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$20.00 - $100.00

description: Rent with us! Duration 7 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and attachments

Nine Day Electric Bike Rental
Book online
$295.00

duration: 9 Days 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 get on...

2026 Juneteenth Food Truck Vendor Registration

Historic Mitchelville Freedom Park

Book online
$206.00

duration: June 13th from 10am- 4:00pm description: **Vendors can sell all food items. Can not sell beverages.** We invite local artists, crafters, food vendors, and nonprofit organizations to join us for a day of culture, history, and community at...

Two Week Bike Rental

Wheelz of Hilton Head

Book online
$85.00 - $170.00

description: Two Week Bike Rental Rates Duration 14 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...

Fishing for 6 or more

May River Excursions

Book online
$375.00 - $675.00

description: *Large fishing trip perfect for families and friends!* ___________________________________ Rates are based on 6ppl **2 Hours** - $375 **3 Hours** - $475 **4 Hours** - $575 *Can take a maximum of 12 people. Each additional person...

Pride on the Pacolet

Vintage View River Retreat

Book online
$20.00 - $45.00

duration: 3 Hours description: Come celebrate Pride Month and light up your weekend! Glide down the river with glowing rainbow gear, good vibes, and nonstop Saturday night fun. This 3 hour adventure lets you float while the sun goes down, laugh with...

North Pole Express

The South Carolina Railroad Museum

Book online
$17.00 - $22.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual holiday ride. Santa walks through the train and comes to you. No lines! The ride lasts about 90 - 120 minutes, or...

Busy Bees Workshop

Coastal Discovery Museum Hilton Head

Book online
$20.00

duration: 1 hour 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 min_age...

Private Lesson with Ed Brill

Palmetto Dunes Golf Academy

Book online
$110.00

description: About Ed Brill Originally from Kalamazoo, MI, Ed Brill received his golf training from Ferris State University. Ed is Titleist TP 1 Level 1 certified and specializes in Aimpoint Technology and V1 Video Technology. Ed is also a...

Hack, Snack and Roadie Ride

Daufuskie Marsh Tacky Society

Book online
$450.00

meeting_point: Varies description: Duration 3.5 Hours Please Note This is experience is designed for novice or better riders who are comfortable with longer hours in the saddle and are able to independently mount/dismount their horses easily...

Firework Cruise

Island Head - Broad Creek

Book online
$39.99 - $599.00

duration: 1.5 Hours 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: Firework Cruise Take in the sights of the Shelter...

WAHHI 2 Hour Guided Kayak Tour

meeting_point: Hilton Head Island, SC description: *Explore Hilton Head's waterways by kayak with an interpretive naturalist guide* --- Description Discover the Hilton Head tidal marsh by kayak… Kayak through the tidal creeks and salt...

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