Hilton Head, SC Vacations

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Featured Vacation Rentals

Newly Renovated Harbour Town Villa with ...

Summary:Ketch Court 824The Space:Ketch Court 824 is conveniently located in the heart of Sea Pines. This freshly remodeled villa features all new furnishings throughout, as well as a roomy, private patio with two outdoor seating areas. The entirely...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Beautiful Sea Pines home with private ho...

Summary:Tupelo CottageThe Space:Tupelo Cottage is a impressive, pet-friendly home in the heart of Sea Pines Plantation. A roomy floor plan, a huge outdoor space, and a private hot tub create a great place for rest and relaxation.Walking through the...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beautifully remodeled villa near the bea...

Summary:Forest Beach Villas 304The Space:304 Forest Beach Villas is a roomy, refreshed third-floor villa located right across the street from the Atlantic Ocean! The open floor plan of this property is sure to delight. The living area features a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
1 Shore Crest, Large Pool, Ping Pong, Be...

1 Shore Crest Lane, Hilton Head Island is a impressive home constructed in 2022 and offers 5 bedrooms & 5 bathrooms, a enormous pool and a calming outdoor entertainment space. This splendid beach home is just a fast 3-5 min. walk to the Burkes...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Coastal condo with pool, tennis, and gym...

Summary:HH Beach & Tennis 158BThe Space:Say hello to the sunshine when you call this Hilton Head HH Beach & Tennis condo your next vacation destination! Right at your stay, indulge in a plethora of astounding shared amenities including a pool,2...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Updated condo in beachfront complex with...

Summary:Carolina Beach Club 427 / PineappleThe Space:Soak up the sun and appreciate a ideal Hilton Head vacation from this modern condo in the oceanfront Carolina Beach Club! Admire the view of the Atlantic Ocean right from your private balcony...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

CCHH Kayak Tour

Outside

Book online
$35.00

meeting_point: Hilton Head Island, SC description: *Explore Hilton Head's waterways by kayak with an interpretive naturalist guide* --- Description Discover the Hilton Head tidal marsh by kayak… Bring the family kayaking through the tidal...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

description: See dolphins in their natural habitat! Duration 2 hours About The Lowcountry is home to several pods of Atlantic Bottlenose Dolphins. Join us for a 2 hour cruise to see them in their natural habitat and take in the beauty...

Five Day Electric Bike Rental
Book online
$250.00

duration: 5 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

PB 7 Hour Ultimate Lowcountry Day
Book online
$110.00 - $1,565.00

description: *Customized adventures are the best way to see and do the Lowcountry!* Description Designed for the family or small group interested in experiencing an authentic day in coastal Carolina. We will give you a menu of options that can...

Baby Gear Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$30.00 - $350.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 14 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean...

Ladies Only Clinic

Palmetto Dunes Golf Academy

Book online
$50.00

description: Learn something new every day! Duration 50 minutes About The Academy presents a daily golf clinic at the Arthur Hills Golf Course, featuring special instruction on the stroke of the day. With a student-instructor ratio of 5:1...

7 HR Ult Day

Outside

Book online
$87.50 - $1,095.00

meeting_point: Hilton Head Island, SC description: *Full day customized adventures are the best way to see and explore the Lowcountry!* --- Description Your Day, Your Way! Outside’s signature program! The Ultimate Lowcountry Day is just...

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

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

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

Day Rental

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: 1 Day description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Additional Fees - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free (1 lock per 2 bikes) About - Perfect for a day...

Three Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$159.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

One Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$20.00 - $100.00

description: 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

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