Hilton Head, SC Vacations

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Featured Vacation Rentals

Charming 3 bedroom 3 1/2 bath home in be...

Isle of PinesOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This striking three-bedroom three and a half bathroom home in the Sea Pines plantation is the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Convenient Location plus Golf Course Vie...

This Hilton Head gorgeous two bedroom, two bath plus additional twin room villa has marvelous vistas of the George Fazio golf course! The kitchen is completely equipped featuring new stainless steel appliances and granite countertops. The...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Sandcastle by the Sea - brand-new, priva...

Sandcastle 97Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Lovely Condo with WiFi, Pool, On-Site Go...

St Andrews Common 1976Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With two bedrooms and two bathrooms, this second-level condo in the St. Andrews Common...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Three-level condo with outdoor pool, pat...

Heritage Villas 2213Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked into a peaceful spot in Sea Pines Resort, this cavernous, three-level condo offers...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Marriott SurfWatch Resort Condo in Hilto...

Located along a handsome stretch of shoreline on fashionable Hilton Head Island, this appealing resort's oceanside setting, comfortable accommodations and fine amenities are sure to impress. With its private oceanfront location, Marriott's...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

Pony Rides

Daufuskie Marsh Tacky Society

Book online
$10.00

Duration 10 minutes About Do you have a child that's either totally horse crazy or slightly horse curious who would delight in a chance to sit in the saddle? Allow us to provide a memorable, confidence building experience while introducing them...

Full Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$90.00 - $125.00

Single Kayak Full Day Rental: $99 ________________________________ Double Kayaks Full Day Rental: $150 _____ Duration 8 Hours

Two Day Double Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$45.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Fishing for 6 or more

May River Excursions

Book online
$375.00 - $675.00

*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 is...

Two Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$40.00 - $200.00

Rent with us! Duration 14 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

Gift Card

Drifter Excursions

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

Wonderful Wings

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $25.00

*Get up close and personal with local butterflies!* ___________________________________ Rates - **$6 per adult, $6 per child (Geared to preschool age & younger children, but fun for the whole family!) - **3 and under, no...

9 Day Rental

Island Life Rentals and Tours

Book online
$39.00 - $275.00

___________________________________ Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles...

Learn to Row

Hilton Head Island Recreation Association

Book online
$40.00

duration: 2 days • 3 hours per Day meeting_point: Rowing and Sailing Center min_age: 11 max_age: 18 group_size: Up to 10 Campers description: Learn the basics of rowing. The camp utilizes 1-4 person shells (boats) and will teach participants...

Single Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$10.00 - $25.00

First come first serve basis, come into shop to rent! Rates - **Uninsex Adult Beach Cruise Bike Rental:** $20 - **Men's Tall Frame Bike Rental:** $20 - **Tandem Bike Cruise Bike Rental:** $25 - **Trike with Basket Rental:** $25 - **24" Kids Fuji...

Sunset Excursion

May River Excursions

Book online
$50.00 - $60.00

*One of our most popular trips!* ___________________________________ Rates **Adult** - $50.00 **Child** - $40.00 ___________________________________ Duration 1.5 hours ___________________________________ About - See one of the most...

One Week - 4 Passenger Quad Stroller Wagon with Removable Canopy

PERFECT CARRIER FOR KIDS – Baby bags. Booster seats. Strollers. Sometimes, taking our little ones on the go with us is nearly impossible! Babies and toddlers alike love strolling around in the WONDERFOLD X4 Wagon, secured in a 5-point harness and...

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