Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

SUPER VALUE VACATION HOUSE: PRIVATE BEAC...

Do you want to savor natural beauty, calming privacy and simple access to this neighborhood’s private wild, uncrowded 2 mile long beach, Lazy River and splash pads, charming recreation, and close by terrific eateries and stores?Here escape the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Long-Term Stays Welcome: HH Island Resor...

Family Friendly | 3 Flat-Screen TVs | Near Kayaking & Biking | Long-Term Stay PricesEndless coastal adventures await when you book this 2-bedroom, 2-bath Hilton Head Island vacation rental! Surf the waves of the Atlantic, embark on a kayaking...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Snowbird-friendly golf getaway near the ...

Queens Grant 662Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Whether you're spending your days calming by the on-site pool, practicing your swing on one of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
High-end home located on the 16th hole o...

Come savor this new high-end home located on the 16th hole of the Robert Trent Jones Golf Course. Everything in this home is new which includes all the furnishings coming from Haverty's. The Kitchen consists of all-bespoke cabinetry, granite...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Charming 2-bedroom resort on Ocean in te...

Welcome to this relaxing resort in Hilton Head. This appealing property offers 2 bedrooms with a king and 2 queen beds, ideal for a modest group of guests. Savor the tremendous amenities like WiFi, AC, activity center, multiple pools, splash pad...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Waterfront Vacation Home with Pool & Hug...

Lands End 39Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’re searching for a cavernous vacation home located just a few steps from the opulent...

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

Hilton Head Tours & Activities

Island Head Inshore Fishing

Island Head - Broad Creek

Book online
$495.00 - $1,125.00

duration: 3 - 8Hours description: Join us for an unforgettable inshore fishing adventure aboard our 21-foot Parker center console. Whether you're a beginner or an experienced angler, our trips are tailored for fun, excitement, and reeling in the...

Discovery Lab Open House

Coastal Discovery Museum Hilton Head

Rates Suggested $5 donation per person (Ages 4+). Children must be accompanied by an adult. Everyone must have fun!! Duration 2 Hours (Drop in any time during Open House hours and stay as long as you'd like!) Discovery Lab During the...

Deliberately Unpredictable: Art Beyond Tradition

Coastal Discovery Museum Hilton Head

duration: various description: Main Gallery Exhibit what_is_included: Art from Cindy Chiappetta, Arla Wible, Vickie Jourdan, Sharon Licata, Mark Larkin, Margaret Crawford, Jo Dye, Earline Allen, Donna Varner, Joanna Chalson, John Crum and Linda Tully

Private Dolphin Discovery Tour - One Hour

Island Life Rentals and Tours

Book online
$35.00 - $250.00

duration: 1 Hour group_size: 12 - 14 Max description: See dolphins up close! Now you can enjoy the thrill of a small boat expedition for nearly the same cost as the big boat "bus tour". Join Island Life for a great introductory cruise through the...

Blue Crab Discovery

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $90.00

*Explore where Atlantic Blue Crabs live, how they impact local communities, and why the Lowcountry enjoys and protects this food source!* ___________________________________ Duration 1.5 Hours ___________________________________ About The...

Afternoon Dolphin Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

See the Coastal Wildlife About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Depending on the time of year...

One Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$20.00 - $100.00

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

Donuts with Santa Cruise

Vagabond Cruise

Book online
$24.95 - $44.95

duration: 60 Minutes cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 accessibility: Not Wheelchair Accessible description: **Donuts with Santa Cruise** Experience the joy of the...

Lake Wateree Private Charters

Captain Jake's Guide Service

Book online
$350.00 - $800.00

duration: 3-8 hours meeting_point: Lake Wylie Boat Ramp-890 Nivens Landing Dr Fort Mill, SC 29708 description: Whether you're looking for an action-packed day of tubing and island hopping or a laid-back cruise to soak in the views, we’ve got you...

Weekend 9:30 am-3:30 pm Golf Cart Rental
Book online
$70.00 - $90.00

Weekend 9:30 am -3:30 pm - Golf Cart Rental *Must have valid Driver's License to rent a cart.*

Fireworks Cruise

Island Time Charters

Book online
$425.00

Duration 2 Hours About This Fireworks Cruise provides a front row seat to one of our Island's most popular events! Enjoy the sunset while dolphin watching and taking in the beauty of the salt marsh ecosystem then stay on board with the best...

Equestrian Lessons - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

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