Hilton Head, SC Vacations

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Featured Vacation Rentals

Near Robert Trent Jones golf course with...
4.0
(3)

This Water Oak villa rental has accommodations for ten and is located near the Robert Trent Jones golf course with just short walk to the beach. The Primary -suite is on the first floor with its king bed, HDTV and private en-suite bathroom. The...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Spacious condo with patio, pool, walking...

Hilton Head Cabanas 3Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in Hilton Head, SC! This gorgeous condo, located in the...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Relaxing Evian condo w/ patio, pool, ten...
4.4
(5)

Evian 172Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You'll have it all with a stay at Evian 172—a striking villa in the Shipyard community that is the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Mid-Island Retreat | 2 Pools, Hot Tub, 1...

Fiddlers Cove 19KOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the gated Fiddler's Cove community, this 2BR/2BA condo offers a calming top-floor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
463 Captains Walk is a gorgeous villa wi...
5.0
(1)

HILTON HEAD. This attractively remodeled oceanfront villa offers gorgeous vistas and a serene ambiance for a really calming stay. Located on the second floor of Captains Walk in Palmetto Dunes Plantation, the villa features a completely equipped...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Steps to Pool & Beach: Family Condo in H...
4.8
(13)

Your dream vacation is soon to be a reality at the well-preserved coastal getaway of Hilton Head Island! This 2-bedroom, 2-bath vacation rental at Hilton Head Resort gives you access to so many inclusive amenities, you may never want to leave the...

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

Hilton Head Tours & Activities

Palmetto Bluff

Flip Flop Charters

Book online
$625.00 - $750.00

Beautiful Scenery Duration - 3 hours - 4 hours About Nestled on the scenic May River is Palmetto Bluff, an idyllic community on 20,000 acres. Within the community is an extensive nature preserve, private residences, a hotel, several...

Pink Moke Rental

Carolina Rides

Book online
$250.00 - $5,000.00

The best way to travel around Hilton Head! Duration Daily & Multi-Day Rentals About Leave your family car behind and rent a Moke for the day, weekend, or your entire vacation! Experience the open air while shopping, visiting friends or just...

New Sailboat Seas The Moment - 2-hour Sunset Sail and dolphin watch

*Sunset Sail* Come end the perfect day with the perfect evening on the water. Enjoy the beautiful scenery and wildlife while enjoying some often-great sailing. End the evening with a beautiful sunset to top it off - Generally great sailing...

Round Trip Ferry Tickets | 9:30am - 3:30pm | Tuesday - Sunday

Round Trip Ferry Tickets to Daufuskie Island for 9:30am - 3:30pm | Tuesday - Sunday Ride the Daufuskie Island Ferry from Broad Creek Marina on Hilton Head Island to Daufuskie Island! • Depart from Broad Creek Marina on Hilton Head Island at...

Santa Elena Society

Coastal Discovery Museum

Book online
$25.00 - $1,000.00

*Donate Today!*

Segways & Smoothies Tour

Island Segway

Book online
$109.00

A Smoothie hits the spot! Duration 1.5 Hours About 50% Ride, 50% Smoothie, 100% Fun Segways are for every day of the week and Smoothies and Boba Tea is refreshing on a HOT day. This Segway tour takes you all around the south end to find an...

Day Camp Sessions

Daufuskie Marsh Tacky Society

Book online
$425.00

Campers learn practical, natural horsemanship and riding skills! Duration 10 minutes About Youth (ages 7-17) are welcome to participate in one or more week long day camp sessions. Campers learn practical, natural horsemanship and riding...

Adventure Camp

Hilton Head Island Recreation Association

Book online
$250.00

duration: 4 days • 3.5 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 30 Campers description: Experience adventure this summer! Participants will make lasting memories of kayaking, stand up paddle...

Private Dolphin Discovery Tour - One Hour

Island Life Rentals and Tours

Book online
$35.00 - $250.00

See dolphins up close! About Our one hour Discovery Tour is a great introduction to Hilton Head Island's beautiful salt marsh environment and dolphin habitat. It's perfect for those with small children, senior citizens, or anyone that wants a...

Guided Kayak Tour

Island Head- Hilton Head Harbor

Book online
$40.00 - $75.00

*Paddle the Low Country!* ___________________________________ Rates **Kayak:** $40 **Tandem Kayak:** $75 *All Ages* ___________________________________ Duration 1 hour and 30 minutes ___________________________________ About Come...

Three Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$135.99 - $271.99

Three Week Rental Rates: - 16” Kids Beach Bike: $135.99 - 20” Kids Beach Bike $135.99 - 24” Youth Beach Bike: $135.99 - 26” Bike w/ Child Seat: $150.99 - 26” Mens Beach Bike: $135.99 - 26” Unisex Beach Bike: $135.99 - 12" Balance...

24  Hour E-Bike Rental(Pick-up/Return between 9 and 4:30)

duration: 24 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 get...

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