Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Pet and Friendly Shipyard Home with 5 Be...

3 Port Au Prince is a marvelous 5 bedroom, 3.5 bath, pet friendly home located in the gated community of Shipyard Plantation. The completely equipped kitchen has granite countertops, new range, island that seats 3, and breakfast table for six...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Close to the Beach! 3 Bed 3 Bath Townhou...

New to Island Getaway - great weeks availableHILTON HEAD ISLAND. The ideal location in Palmetto Dunes is available to you! At the end of the complex just off the beach path, you won’t find a better spot! The first thing you will notice upon entry...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Ocean View , Top Floor, 6502 with roof, ...

Feel the tranquility of oceanside living in this meticulously appointed two-bedroom villa, boasting an awe-inspiring ocean panorama. Whether from the master bedroom, cavernous living area with new furnishings, or the broad top-floor balcony complete...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
424 Captains Walk has panoramic ocean vi...

This fourth floor penthouse in Captain's Walk is the ideal setting for your next vacation. Upon entering the unit, guests will savor expansive vistas of the Atlantic. The living room has two enormous couches, game table, and TV. The dining room has...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
WATCH DOLPHINS PLAY ALL DAY!  Newly reno...

OCEANFRONT DOLPHIN WATCH! This impressive villa has been completely re-decorated by a professional designer! The view is spectacular. You will be able to watch dolphins play all day in this handsome condominium! Savor a impressive, unobstructed...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Sunset Rentals | Beachwalk 165 | Dog Fri...

A completely refreshed first floor and painless access to many amenities await you in this immaculate, pet-friendly villa tucked in a peaceful corner of Beachwalk Villas in Shipyard, Hilton Head Island. As you enter, you are welcomed into the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Surfing Lessons

Hilton Head Island Recreation Association

Book online
$100.00

duration: 1 hour & 15 minutes meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 min_age: 5 group_size: Up to 10 people description: Learn to Surf in the safe and warm waters of Hilton Head Island! Our safe...

PB 2 Hour May River Kayak Nature & History Paddle

On this casual tour, you'll explore the local creeks with a naturalist guide. No kayak experience is necessary. Duration 2 hours Meeting Location - This activity will meet at the Paddle House which is located underneath the Canoe Club...

Little Swingers

Palmetto Dunes Golf Academy

Book online
$50.00

Duration & Rates - 45 minutes - $50 per student Little Swingers (offered seasonally) Mondays from June 9th - August 25th, 2025 Learn fundamentals of golf while singing songs, causing amazing retention and success. 5:1 Student-Teacher ratio...

Two Day Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$69.99

Rate Two Day Rental: $69.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 2 Days

Private Afternoon Half Day Sail On Knot The Office
Book online
$1,050.20

duration: 4 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 we can...

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 Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

Three Day Rental Rates: - 16” Kids Beach Bike: $45.99 - 20” Kids Beach Bike $45.99 - 24” Youth Beach Bike: $45.99 - 26” Bike w/ Child Seat: $60.99 - 26” Mens Beach Bike: $45.99 - 26” Unisex Beach Bike: $45.99 - 12" Balance Bike...

1 Hour Lane Rentals

Palmetto Axes

Book online
$25.00

Includes Coaching to Help Make you a Star! Duration 1 Hour About Test your luck hurling axes for one hour eventually learning to hit the bull’s-eye along the way. You might meet your new best friend as you share the lane and fun with...

Kayak Tour

Port Royal Sound Foundation

Book online
$40.00 - $55.00

duration: 2 Hours description: Join a PRSF Naturalist for a 2-hour guided kayak tour of the Chechessee River departing from the Maritime Center. Children ages 5-12 must be on a tandem kayak with an adult (18+). Designed for all experience...

13 Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$102.18 - $243.23

Enjoy miles and miles of scenic bike paths Duration 13 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also available ...

Three Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99 - $199.00

Single Kayak Full Day Rental: $175 ________________________________ Double Kayaks Full Day Rental: $250

Fishing Charter - Kahuna

Native Son Adventures

Book online
$365.00 - $1,260.00

Duration 3 to 8 Hours About In-Shore and Near-Shore Fishing. The most stable adventure vessel on Hilton Head Island! The 26 foot Glacier Bay catamaran is the cream of the crop! He does it all, so let’s go have some fun! Bean bags lots...

Find your perfect Hilton Head

Fishing Charter

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