Hilton Head, SC Vacations

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Featured Vacation Rentals

Nautical condo with a balcony, & AC - cl...
4.5
(13)

Bluff Villas 1716Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located at the tip of Sea Pines, this sunny and completely-updated villa is ready to host you...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Double Master Suite Luxury 4 BR Sea Pine...

Wonderful luxury Sea Pines four bedroom home with private pool and spectacular vistas of the live oaks wrapping around the golf vistas. Pretty high ceilings with giant kitchen and tons of living space outdoors. Oversize kitchen and dining area...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Dog-Friendly Condo w/ Fast WiFi, a Patio...
4.7
(11)

Stones Throw 30Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located less than a half-mile from Folly Field Beach, this roomy, family-friendly condo is...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Hilton Head Vacation Rental for the Whol...
4.2
(5)

This Hilton Head condo rental is a golfer's dream! Cavernous town home with a sizable private deck with grille and seating overlooking the lagoon with fountain. You cannot beat the price, size, and overall value of this property. Brand-new carpet...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
1 Shore Crest, Large Pool, Ping Pong, Be...
4.8
(4)

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

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Charming, family-friendly condo w/ priva...
4.6
(14)

Turnberry Village 251Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sunkissed skin and salty air await you at this Hilton Head Island getaway. Sporting a...

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

Hilton Head Tours & Activities

Two Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$25.99

Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

Lowcountry Seafood Experience

May River Excursions

Book online
$135.00

Rate - $135 per person includes boat excursion as well as a meal and one beverage __________ Duration - 2 Hour Boat Excursion with meal afterwards at Hudson's ____________ About - A two hour excursion that includes instruction on...

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...

Paddle Splash Party

Hilton Head Island Recreation Association

Book online
$40.00 - $400.00

duration: 2 Hours meeting_point: Rowing and Sailing Center group_size: 15 description: Are you celebrating a birthday or want to schedule a group outing? Request a kayak, paddleboard or fishing party! Parties include a two-hour rental of...

Round Trip To Downtown CHS

Daniel Island Ferry

Book online
$10.00 - $26.00

duration: 30 Minutes meeting_point: description: The boat departs from Daniel Island for service to downtown Charleston's Waterfront Park. The trip takes approximately 30 minutes. what_is_included:

The Shores of Asbury - Jet Ski Rental

Captain Cams Watersports

Book online
$90.00 - $325.00

duration: 1-7 Hours meeting_point: 1600 Asbury Park Road, Anderson, SC 29625 min_age: 25 group_size: Up to 8 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight of the...

Beach Gear Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$40.00 - $200.00

Everything you need for a fun and comfortable day at the beach! Duration 13 Days About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than 5PM. ...

Art Market: Fine Art and Craft Festival Tickets

Coastal Discovery Museum Hilton Head

Book online
$5.00

$5 per adult, FREE for ages 12 and under Original art for sale Food and drink available for purchase Advance tickets are not required, but only cash will be accepted for entrance on site. Stroll the grounds of picturesque Honey Horn to find...

Private Beach Sail On Hobie Catamarans

Hilton Head Island Recreation Association

Book online
$275.00

duration: 1.5 hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 group_size: Up to 4 people description: 1.5 hour, up to 4 participants. Take a ride on our 17’ Hobie Getaway with one of our US Sailing...

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...

Daufuskie Island to Hilton Head

Island Head - Broad Creek

Book online
$10.00 - $30.00

duration: 45 Minute Ferry Time cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Freeport Marina Daufuskie Island, SC description: Daufuskie Island Daily Return Trip We offer...

One Day Surf Board Rental

Hilton Head Outfitters - Bike Rental

Book online
$49.99

Rate 1 Day Rental: $49.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 8 Hours

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