Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Direct Ocean View Condo with balcony, po...

HH Beach & Tennis 302AROur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'**Need to Know Notes**Admiral's Row Sprinkler ProjectAnticipated Start date...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Welcoming Condo with Lagoon Views, Deck,...

Beachwalk 142Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beachwalk 142 is an ideal spot for athletes because the property has options for basketball...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Couples Retreat, Dog Friendly, Private e...

Ready for coastal breezes, fruity umbrellas in your drink, and some serious R&R? Then Latitude Adjustment is just what the doctor ordered. A ideal couples getaway. 6/10 a mile to the beach, 15 min walk or 5 min bicycle ride via enormous sidewalks...

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

HH Beach & Tennis 158BOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say hello to the sunshine when you call this Hilton Head HH Beach & Tennis condo your...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Snowbird-friendly studio condo near beac...

Bluff Villas 1799Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located within a short walk to the beach, this ground-floor, water-view condo...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
Comfortable condo with a pool, hot tub, ...

Fiddlers Cove 16DOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Golfers and beach bums alike will appreciate this comfortable condo, just mins. from multiple...

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

Hilton Head Tours & Activities

Monkey Safari

Hilton Head Helicopter Tours

Book online
$369.00

Come see this magnificent fort, beaches and property from the air! Duration - **45 minutes** About - Along the way you will see old lighthouses, breath-taking coastal views of the Low Country, and small remote islands only few have ever...

Two Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$35.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

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...

One Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$21.99

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.

Donuts with Santa Cruise

Vagabond Cruise

Book online
$24.95 - $44.95

duration: 60 Minutes cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 accessibility: Not Wheelchair Accessible description: **Donuts with Santa Cruise** Experience the joy of the...

Sunset Dolphin Cruise Aboard Dolphin Seafari

Rates - Adult - $45 - Children -$30 (12 & under) - Infants -$10 (2 & under) ___________________________________ Duration - 1 hour and 30 minutes ___________________________________ About We have been voted the Best Dolphin tour on...

Paws on the Pacolet

Vintage View River Retreat

Book online
$15.00 - $45.00

duration: Hourly meeting_point: 250 Phifer Line Rd, Spartanburg SC 29307 description: Paws on the Pacolet is Vintage View Adventures' dog-friendly kayak experience designed for you and your four-legged best friend! Enjoy a relaxing paddle on the...

One Week Bike Rental

Wheelz of Hilton Head

Book online
$50.00 - $210.00

One Week Bike Rental Rates Duration 7 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect getting around...

Private Family Or Group Fishing Trip Aboard The Drifter

duration: 3 Hours cancellation_summary: 72 Hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way group_size: 32 people pricing: The Private Family or Group Fishing Trip Aboard the Drifter has a set price of $995 for a group size of 16 people or...

One Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$25.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Lowcountry Lunch Cruise (Outside Dining)
Book online
$40.00 - $69.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Not wheelchair accessible description: ![Description of image](https://cdn.filestackcontent.com/bnLlDRzMSPaudj3mMT5x) Book Online and Skip the...

Private Dolphin Discovery Tour - One Hour

Island Life Rentals and Tours

Book online
$35.00 - $250.00

duration: 1 Hour group_size: 12 - 14 Max description: See dolphins up close! Now you can enjoy the thrill of a small boat expedition for nearly the same cost as the big boat "bus tour". Join Island Life for a great introductory cruise through the...

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