Hilton Head, SC Vacations

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Featured Vacation Rentals

6 Terra Bella, Oceanfront, Elevator, Pri...

**NOW OFFERING 50% OFF POOL HEAT FOR MARCH - MAY 22*** UPON BOOKING, GUEST MUST LEAVE IN COMMENTS THAT THEY WANT POOL/ SPA HEAT OR CALL OUR RESERVATIONS TEAM TO CONFIRM. THIS IS FOR NEW BOOKINGS MADE ON OR AFTER 1/30/26***6 Terra Bella Trace, Hilton...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Family-Friendly Condo with WiFi, Pool, H...

Island Club 4304Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal temperatures and ocean breezes beckon you outdoors at this beachfront rental on Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Spacious and Cozy Oceanside Retreat! Zer...

Managed professionally by Vacation Time of Hilton Head, our oceanfront complex is appealingly booked directly through our website.Welcome to Hilton Head Beach Villa 12!Exciting News: Our Striking New Swimming Pool is Now Open!Located on South Forest...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Homey Condo with Lagoon View from Balcon...

Island Club 122Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'When you book this comfortable Island Club condo, you’ll be able to prepare healthy meals by...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Updated Oceanfront Two Bedroom Condomini...

You'll be glad you chose this two bedroom oceanfront Hampton Place condominium. The kitchen is gorgeously refreshed with bespoke cabinetry, granite countertops and stainless steel appliances. Kitchens come entirely-equipped, making cooking for the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Luxurious bohemian home with large deck,...

Fawn Lane RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Boho-chic and modern luxury combine in ideal unison at this splendid Hilton Head Island home...

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

Hilton Head Tours & Activities

Sunset Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

description: Experience the breathtaking beauty of the Sunset Tour on our Glowing Bicycles! Duration 35 minutes About Join us for a mesmerizing 35-minute Sunset Tour while riding on glowing bicycles! Witness the enchanting beauty of Hilton...

PB Private Biking the Bluff
Book online
$75.00 - $265.00

meeting_point: Palmetto Bluff

Sunset Beach Photography

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations may be rescheduled or fully refunded if no suitable time is found meeting_point: 64 Bradley Beach Road, Hilton Head Island, SC 29928 description: Want to commemorate a special...

Single Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$10.00 - $25.00

description: 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 ...

Flyboard 40 Minute

Carolina Hydrofly

Book online
$139.00

description: 40 Minute Flyboard Pro Series Experience About Each guest will have 30 minutes of flight time and 10 minutes of instruction time. If you would like to book for more than one person, then please process one booking per person by...

11 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$45.00 - $315.00

duration: 11 Days cancellation_summary: 24 Hours in advance 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...

Hilton Head Yacht - Dinner Cruise

Salt Shaker Charter LLC

Book online
$4,900.00

duration: 4 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: An Evening Aboard Salt Shaker: Gourmet Dining Meets Sunset Serenity! Aboard Salt Shaker, every moment is...

Butterfly Learning Station

Coastal Discovery Museum Hilton Head

meeting_point: Coastal Discovery Museum description: About Experiencing the enchantment of a native butterfly garden and observing all four stages of the butterfly life cycle is a unique opportunity available to people of all ages at the Coastal...

All-Inclusive Sunset Supper Cruise

Daufuskie Difference

Book online
$44.50 - $89.00

meeting_point: Old Daufuskie Crab Co. Restaurant description: Join us on the most popular Sunset Dinner Cruises Hilton Head has to offer! Departing from Broad Creek Marina every Friday at 4pm. The 50-minute Ferry ride is accompanied by fascinating...

Five Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

description: Electric Bike Rental Duration 5 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

Eight Hour Private Offshore Charter
Book online
$1,800.00

group_size: For up to 6 guests description: Spend a full day fishing the productive reefs around Hilton Head Island aboard the Sweet Pea, a 27 ft. Glacier Bay twin-engine cat equipped with modern electronics and tackle. Your certified and...

Surf and Sail Camp

Hilton Head Island Recreation Association

Book online
$275.00

duration: 4 days • 3.5 hours per Day meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 min_age: 7 max_age: 15 group_size: Up to 20 Campers description: Join us for an exhilarating 4-day camp combining the thrill...

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