Hilton Head, SC Vacations

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Featured Vacation Rentals

2516 Villamare - Nicely updated fifth fl...

This fifth floor condo is gorgeously refreshed throughout with tile floor and modern beach decor. The Kitchen features tile countertops, stainless steel appliances and bespoke cabinetry while being completely-equipped with all the luxuries of home...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
4 Bedroom 4 Bath house on the 11 mile la...

Discover the ideal island escape at this 4-bedroom vacation rental located on the pristine 11 Mile Lagoon. Ideal for families, groups, and friends traveling together, this waterfront lagoon-side home offers comfort, space, and unbeatable access to...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Ideally located condo with pool, tennis ...

Summary:Beckenham 103The Space:Beckenham 103 is an charming condo in Port Royal Village, just a fast walk to the beach. For even faster transportation, you'll have access to two bicycles. There is a lot to boast about with exceptional upgrades...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
5 Sandy Beach Trail- Beach House w/ Priv...

"Sail Away HHI" is a grandiose 4500 square foot, 6 bedroom, 6 full bathroom (plus 1 half bath) home located steps away from the beach access. Located in the beautiful Burkes Beach community of Hilton Head Island, (rated as the best beaches in...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 19
Family-Friendly Villa with Shared Pools ...

Summary:Island Club 6102The Space:Bring along your friends and family members when you visit this comfortable Island Club villa. It's just steps from a sizable shared lap pool and hot tub, miles of beaches, and a play area for kids complete with a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beachfront/Oceanfront Hilton Head Island...

This Breakers beach/oceanfront condo is a great location for families; steps away from the complex pool with the beach and ocean just beyond. The unit is located adjacent to the elevator. Conveniently located across from Coligny Plaza with...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 5

Hilton Head Tours & Activities

Private Sunset Cruise (Up to 14 Passengers)

Island Head- Hilton Head Harbor

Book online
$549.00 - $699.00

meeting_point: 43 Jenkins Rd, Hilton Head, 29926, South Carolina description: The private sunset cruise is the perfect way to end a day on Hilton Head Island. There is nothing quite like a low country sunset, especially seeing one from the water...

Paint the Pony - Montage Guests
Book online
$170.00

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

One Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$39.99 - $129.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Inshore Fishing

May River Excursions

Book online
$375.00 - $775.00

description: *Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* ___________________________________ Rates are per private charter **2 Hours** - $375*-Only Recommended for Small Children* **3 Hours** ...

Suns Out Floats Out Float-a-Palooza
Book online
$5.00 - $25.00

duration: 12pm-6pm max_age: 101 group_size: 200 description: Get ready for two full days of floating fun at Saluda Lake Landing during our Suns Out Floats Out Float-A-Palooza! Join us June 13–14 for DJs spinning all weekend long, cold drinks...

Bachelor/Bachelorette

Flip Flop Charters

Book online
$895.00

description: Explore Calhoun Street! Duration 4 hours About If you’re looking for a picturesque location to raise a glass and toast the happy couple, we’d love to help you celebrate! Waterfront bars are an excellent choice. With a...

Ten Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$78.60 - $187.10

description: Enjoy miles and miles of scenic bike paths Duration 10 Days About Free locks with all rentals. Baskets and helmets also available - please select during check-out! More info Free locks with all rentals - please select...

Blue Granite Express

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Guests enjoy a narrated 90-minute trip through Fairfield County countryside. Seating on the train is on board an open-air car, allowing easy viewing as...

Solaris - Destination Charter
Book online
$395.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Customize your luxurious destination charter aboard Solaris today! **Our private charters accommodate up to ten passengers...

Fall Speaker Series: Legends & Luminaries of Hilton Head Island

duration: 1.5 hrs cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: Join the Coastal Discovery Museum as we commemorate our 40th...

Creature Feature

Coastal Discovery Museum Hilton Head

Book online
$7.00

duration: .75 cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: The Lowcountry is home to an incredible variety of fascinating creatures...

Bike Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

duration: 7 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: Confirmation will include your lock combination in addition to delivery and pick up...

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