Hilton Head, SC Vacations

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Featured Vacation Rentals

Sunset Rentals | Breakers 117

Breakers 117 is a delightfully refreshed oceanfront condo with vistas of the Atlantic Ocean and the community pool. This end unit is located as close as can be to the pool and beach access and provides guests with an open concept floor plan with...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Great Hilton Head Location Pet Friendly,...

This property is now under new ownership and the owners are keen to make this already handsome and cavernous home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a striking 6-bedroom, 5.5-bathroom, pet...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Ground level condo with pool, golf & Sea...

Summary:Plantation Club 464The Space:Feel Hilton Head to the fullest in this adorable condo sporting golf course vistas! From the coastal chic decor to the bright interior, this is the ideal place to call home for your next family hideaway or golf...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunny condo with central AC, pool, tenni...

Summary:Xanadu B10The Space:Located in the heart of Hilton Head Island's Forest Beach area, this serene condo is ready to host you and your guests for the ideal beach vacation! Appreciate on-site access to a shining, outdoor pool, two tennis courts...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Stunning Condo in Plantation Club with V...

Vista Verde - Vacation Units by Five Star Properties“Vista Verde”….Green sprawling vistas abound as soon as you take your first step into this 2-bedroom 2-bath upgraded Hilton Head condo rental at Plantation Club villa. All this, just a short...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Twin Oaks 207  3 bedroom Villa in Hilton...

Summary:Twin Oaks 207The Space:Adventure awaits you in this handsome condo which sits between the 9th and 10th fairways. You will adore sitting on the patio or balcony with your morning coffee or evening beverage. Inside you will find everything you...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Adopt-a-Dolphin

Coastal Discovery Museum

Book online
$50.00 - $100.00

description: About Sixty percent of all adoption money goes directly to the scientists who are studying these magnificent mammals and helps fund interns studying these dolphins, boat fuel, and supplies needed for the Marine Sensory and...

Solaris - Fireworks Cruise

Vagabond Cruise

Book online
$695.95

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Book the Hilton Head summer time favorite Fireworks Cruise aboard the all new Solaris! **Our private charters accommodate up to 10...

Pirate Cruise

Pirates of Hilton Head

Book online
$15.00 - $44.99

duration: 1.5 hours cancellation_summary: Full refunds with 48 hours notice meeting_point: 149 Lighthouse Rd, Hilton Head Island, SC, 29928 accessibility: Ramps lead to the ship; boarding requires 2 steps up, 1 step over and about 3–5 steps to a...

3 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$21.00 - $140.00

duration: 3 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 hours...

Rosé Fireworks Sail

BC2 - Island Head

Book online
$19.99 - $89.00

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

10 Day Rental

Island Life Rentals and Tours

Book online
$42.00 - $295.00

duration: 10 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Guided Paddleboard Tour

Island Head- Hilton Head Harbor

Book online
$40.00

description: *Be one with the water* ___________________________________ Rates **Person:** $40 *Ages 12+* ___________________________________ Duration 1 hour ___________________________________ About Stand Up Paddleboarding focuses on...

Public Sunset Sail on Knot The Office

Anchors Away Sailing Charters

Book online
$110.00

duration: 2–2.5 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 people accessibility: Limited Handicap accessibility, Please call us to ensure...

Two Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$100.99 - $201.99

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...

Beach Comber & Vanishing Island

Dolphin Discoveries Hilton Head

Book online
$69.75 - $395.00

duration: 3 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...

Private Sunset & Fireworks Cruise - 6p

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...

SCM Shark Fishing
Book online
$495.00 - $625.00

meeting_point: Hilton Head Island, SC description: *Catch a shark and get out on the water at the same time!* --- There are few things more exciting than hooking a shark! Our three-hour evening shark fishing excursion includes boat, bait...

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