Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Coastal charm villa with golf-course vie...

Water Oak 17Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to luxury at this striking two-bedroom, three-bath end-unit condo located on the impressive...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Fantastic Vacation Condo Close to Beach ...

Beckenham 205Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beckenham 205 is a elegantly updated two-bedroom, two-bath villa located in Port Royal Village...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
First Floor Condo near the beach with be...

Shorewood 107Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate beach hideaway at this impressive oceanfront condo in Hilton Head, SC. Just...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Inviting Townhome w/ Balcony & Private G...

Shipmaster 1301Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Shipmaster 1301 is an inviting, family-friendly townhome located in Shipyard, just a short...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2 Bedroom Centre Court Villa with Lagoon...

This villa is centrally located within the Palmetto Dunes Tennis & Pickleball Center. It’s ideal for golfers, pickleballers, and tennis players. Let’s not forget the families who want to spend time at the beach. A short, level 10-min. walk...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beautiful condo close to tennis/pickleba...

Queens Grant 578Our 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 coastal getaway in Hilton Head, SC! This gorgeous dog-friendly condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5

Hilton Head Tours & Activities

3 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$21.00 - $140.00

duration: 3 Days 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...

Beaufort Lands End Paddling

Book online
$40.00 - $60.00

duration: 1.5-2 hours meeting_point: Russ Point Boat Landing, Sea Island Pkwy & Fripp Island Bridge (across from Nature Center) description: Join us for a one-of-a-kind kayak adventure, perfectly timed with the high-tide, offering exclusive access...

Shark Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $620.00

Shark fishing is an exhilarating and challenging endeavor that takes anglers on a thrilling journey! Duration 2 to 4 hours About As a captain, I've guided countless shark fishing trips, and each one brings its unique sense of...

Dolphins, Sharks & Shells!

Dolphin Discoveries Hilton Head

Book online
$475.00 - $1,065.00

duration: 3 to 6 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

Marriott Vacation Club Dolphin Eco

Outside Hilton Head’s Dolphin Eco Tour is one of the most popular tours on Hilton Head Island, providing an unforgettable experience for nature lovers, families, and anyone looking for a fun and educational adventure on the water

Fireworks Cruise Aboard Dolphin Seafari
Book online
$35.00 - $50.00

Fireworks Cruise Fireworks Tour begins at 7:30 Sharp! We our on our 30' covered pontoon boat, with a restroom on board!! Coolers are welcomed!! We will enjoy a dolphin/nature tour till the sunsets and than while still on the water watch the...

Stand Up Paddle Boarding Tour

Hilton Head Island Recreation Association

Book online
$40.00

duration: 1.5 hours meeting_point: Rowing and Sailing Center description: Your 1.5hr stand up paddle board trip will explore the marshes of Skull Creek. An educational Lowcountry experience learning and working with the tides, oysters, and...

Tubing and Dolphin - 16 max

This 3 hour excursion starts with our most popular Eco trip on pristine Broad Creek. From here We will cross the Calibogue sound into one of our beautiful tidal rivers. Once here we will inflate the tube and pick up the pace exploring the tidal...

Kayak Rentals

Hilton Head Island Recreation Association

Book online
$25.00 - $165.00

duration: 1 hour meeting_point: Rowing and Sailing Center description: Explore the scenic waterways of Hilton Head with our Kayak rentals! Our top quality kayaks are perfect for all experience levels. Enjoy a peaceful ride as you take in stunning...

Otter Island Sailing Adventure

Otter Sailing Adventures LLC

Book online
$700.00

An all day private sailing adventure! Duration 8 hours About An all day private sailing adventure with an incredible destination, the remote and uninhabited Otter Island with miles of beach that you often have all to yourself. The...

Gift Cards

Shelter Cove Marina Boat Rentals

Kayaking Dolphin Nature Tour

Kayak Hilton Head

Book online
$41.00 - $99.00

See Bottlenose Dolphins! Duration 2 Hours *Please arrive 30 minutes prior to your scheduled tour time* Discount CURRENT COUPON -- $10 off each adult, 50% off each child 12 and under. (Coupon also available in print form but discount cannot...

Find your perfect Hilton Head

Fishing Charter

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