Hilton Head, SC Vacations

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Featured Vacation Rentals

Very Nice Ranch-Style Home Located on 11...

You will be impressed by this freshly modernized home within Palmetto Dunes Resort! The Kitchen features Granite countertops, stainless steel appliances, and bespoke cabinetry. The Kitchen will be completely equipped with all the amenities of...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront condo with WiFi, pool, hot tu...

Summary:Island Club 6501The Space:With elegant ocean vistas from your private balcony, additional seating in the living room area, and refreshed bathrooms, this Island Club rental is the ideal destination for your next beach vacation.The Island Club...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Spacious Villa with Shared Pool, Hot tub...

Summary:Island Club 113The Space:Visit this newly modernized roomy Island Club villa to appreciate an adult calming pool and hot tub, shared kid's pool, tennis courts, tanning facilities, and more!Located just a few miles from Islanders Beach Park...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beautiful Palmetto Dunes Villa- Lagoon V...

Queens Grant 762Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your serene hideaway in Hilton Head, SC! This gorgeous three-bedroom...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Oceanfront Villa with Shared Pools, Hot ...

Villamare 1407Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Oceanfront villa just refreshed, steps from the beach, sizable pool, and hot tub!Pristine...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beachfront beauty with pool access - fir...

Sea PointeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This elegant five-bedroom home is just steps away from Singleton Beach and the shared community...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

One Day (24-Hour) Golf Cart Rental

Wheelz of Hilton Head

Book online
$240.00 - $320.00

description: Golf Cart Rentals! Duration 24 hours Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked...

Harbour Town Happy Hour Cruise
Book online
$29.95 - $64.95

duration: 1.5 meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 accessibility: No, their is a step up onto the boat. description: Join us for the Harbour Town Happy Hour Cruise, a casual, fun, and family-friendly 90-minute...

Sunset and Fireworks Kayak Tour
Book online
$55.00 - $125.00

description: *Few experiences are more memorable than watching fireworks from the seat of a kayak.* --- > Rates >- **Adults Single Kayak:** $55 >- **Adult & Child Double Kayak:** $90 >- **Two Adult Double Kayak:** $110 --- ...

Lighthouse Tour

Hilton Head Helicopter Tours

Book online
$369.00

cancellation_summary: Cancellations accepted up to 24 hours before the scheduled tour. description: See a magnificent fort, lighthouses, beaches and private coastal property from the air on a scenic helicopter flight. Enjoy sweeping Low Country...

Private Sunset & Fireworks Cruise - 12p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

description: Duration 3 Hours About Learn the secrets of Hilton Head’s history and the fascinating stories that bring it to life. This 3-hour expert guided tour takes you to five nearby historic sites in an air-conditioned bus. You will...

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

meeting_point: Hilton Head Island, SC description: Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to...

Bike Rental • Six Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Rent Bikes and Gear Accessories for your vacation! Duration 6 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Fishing Trip

Reel Job Charter Fishing

Book online
$595.00 - $1,195.00

description: Fishing with Reel Job is sure to give you lasting memories! Rates All ages welcome aboard! - 4 Hour Charter - $595 - 5 Hour Charter - $695 - 6 Hour Charter - $795 - 8 Hour Charter - $1195 Please note, this price is a base price...

Private Sunset Cruise (Up to 14 Passengers)
Book online
$549.00 - $899.00

duration: 2 or 3 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 14 Passengers description: The private sunset...

May River Ecology Excursion

May River Excursions

Book online
$40.00 - $50.00

description: *Learn about the ecosystem and wildlife of the May River!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ Duration 1.5...

Firework Cruise

Island Head - Broad Creek

Book online
$39.99 - $599.00

duration: 1.5 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Firework Cruise Take in the sights of the Shelter...

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