Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Coastal Retreat with Patio, Shared Pools...

Fiddlers Cove 17COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor a calming hideaway in this two-bedroom, two-bath Fiddlers Cove villa. This condo has...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Charming Oceanview Retreat! Recently Rem...

Managed professionally by Vacation Time of Hilton Head, our oceanfront complex is appealingly booked directly through our website.Feel Coastal Luxury in This Stunning Oceanview Villa: Hilton Head Beach Villa 16!Exciting News: Our Striking New...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Sea Pines Home with firepit, deck and cl...

Pretty LawtonOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in handsome Sea Pines, Hilton Head, SC! This appealing home is...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Charming Villa with Ocean Views, Pool, &...

Island Club 3204Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With walk-out access to the beach and many community activities, this Island Club villa makes...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Walk to Beach & Golf Club: Hilton Head H...
5.0
(5)

Pack your beachwear and golf clubs to prepare for an ultimate South Carolina escape. Located a short walk or bicycle ride from Shipyard Beach access and golf course, this 3-bedroom, 2-bath home puts Hilton Head’s historical attractions...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Delightful Condo with WiFi, Pool, Tennis...

Ocean Cove 824Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bring your group to this Ocean Cove condo for a beach vacation. This two-bedroom getaway has...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Carolina HydroFly Parties

Carolina Hydrofly

Book online
$800.00 - $1,600.00

Private Party About Enjoy a 4 or 8 Hour Group Lesson. Can have up to 8 people (Half day) & 16 people (Full day) in your party. - Includes 10 minutes of instruction time, fuel, life jacket, and helmet **What's Included** - Helmet - Life...

3 Hour Evening Shark Trip

Black & Blue Charters

Book online
$625.00

*3 Hour Evening Shark Trip* Duration 3 Hours About Evening shark fishing in calm waters. Great trip for kids.

1 Week Rental (Walk Up)

Island Life Rentals and Tours

Book online
$33.00 - $235.00

duration: 1 Week 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 self pick up and drop off available...

Private Fishing Charter

Stray Cat Charters

Book online
$500.00 - $2,200.00

duration: 2 to 10 Hours meeting_point: Hilton Head Island description: The Stray Cat can take up to six passengers. If it is in shore sport fishing our local waters or off shore deep sea fishing, stray cat charters is the experience you are looking...

Two Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$63.99 - $79.99

Single Kayak 2 Hour Rental: $53.99 ________________________________ Double Kayaks or Canoes 2 Hour Rental: $66.99 __________ Triple Canoe 2 Hour Rental: $79.99

Private Food Tour

Food Tours Hilton Head

Book online
$695.00

Customize Your Tour! Duration 3 hours What's Included: - A private luxury SVU pickup for 6 - A knowledgeable tour guide About This tour is made especially for you. After you book the tour, our tour guide will contact you and find out...

HH Seafood Festival: Ohana Fireworks Cruise

A special cruise on the luxury power catamaran, Ohana. This leisurely sunset dolphin cruise will end with the best seat in the house for the fireworks show! Departing Saturday, February 26th 5-7pm $115 per person (includes Kettle One signature...

Sallie Ann Authentic Gullah Tour

Daufuskie Island Gullah Heritage Society

Book online
$70.00

See and enjoy a Gullah Tour on Daufuskie through the eyes and memories of a sixth generation Gullah native! Duration 3 Hours About We are a non-profit organization. Take a relaxing boat ride to Daufuskie, where you will be greeted at the...

Private Sunset & Fireworks Cruise - 16p

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 beautiful Lowcountry sunset! After the sun goes...

Alligator & Wildlife Tours
Book online
$22.00 - $350.00

duration: 1 hour cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Fish Island Sea Pines Forest Preserve group_size: Up to 12 passengers description: Join us on a 1-hour guided tour of the...

General Admission

Bee City Zoo

Book online
$17.00 - $19.00

Come explore our honeybee farm, interactive zoo, gift shop, cafe, nature trail, & nature center! Duration General Admission tickets are good for an *entire* day at the zoo! Please note you can always purchase tickets the day of your visit at...

Golden Hour Sunset Sail

BC2 - Island Head

Book online
$19.99 - $99.00

duration: 2 Hours meeting_point: Board Creek Marina 18 Simmons Rd. description: Smooth sailing, stunning views, and something for everyone. Golden Hour Sail is a luxury sunset experience designed for all kinds of groups—families, friends, couples...

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