Hilton Head, SC Vacations

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Featured Vacation Rentals

Beautiful lagoon views, new living room ...

Welcome to your coastal getaway in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island! This handsomely appointed 4 bedroom, 4 bathroom townhome offers the ideal blend of indoor comfort and outdoor tranquility, attractively located...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
SAVE! FALL&WINTER DATES.ABSOLUTELY BEAUT...

PERFECT WINTER GETAWAY FOR SNOWBIRDS SEEKING A BEAUTIFUL AND COMFORTABLE, STREET ENTRY VILLA IN PALMETTO DUNES RESORT. An definitely impressive family vacation villa in Top Rated Palmetto Dunes Resort in HHI. A ideal family hideaway and location...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beachy condo w/shared pools, WiFi, balco...

Sea Side Villas II 285Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate beach hideaway at this appealing oceanfront condo in Hilton Head, SC...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Amazing Family-Friendly House w/ Private...

High Water 9Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An broad luxury home in Palmetto Dunes, High Water 9 features a single-level layout with seven...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 22
Vibrant condo with tennis courts, pool, ...

Spa On Port Royal Sound 3322Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You won't want to miss this calming slice of serenity for your next vacation trip...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
HEATED OUTDOOR & INDOOR POOL! Monthly Ra...

Welcome to OCEAN'S EDGE - a comfortable and delightfully designed Vacation Ready Services condo located at Hilton Head Resort! Located on the 3rd floor of Building #4, this two bed & two bath island hideaway is the ideal getaway for families...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5

Hilton Head Tours & Activities

One Month Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$180.99 - $361.99

One Month Bike Rental Rates: - 16” Kids Beach Bike: $175.99 - 20” Kids Beach Bike $175.99 - 24” Youth Beach Bike: 175.99 - 26” Bike w/ Child Seat: $190.99 - 26” Mens Beach Bike: $175.99 - 26” Unisex Beach Bike: $175.99 - 12" Balance...

CFT Merchandise

Columbia Food Tours

Book online
$2.00 - $30.00

We have products we'd love to share with you to help you remember the great time you had on our Columbia Food Tour.

Pluff Mudder Summer Camp

Port Royal Sound Foundation

Book online
$445.00

duration: Monday-Friday cancellation_summary: Due to limited space and high demand for our Pluff Mudder Summer Camps, all payments are non-refundable. Please let us know as soon as possible if you have to cancel your reservation so we can fill your...

Seasonal Fireworks Cruise

Flip Flop Charters

Book online
$775.00

Watch fireworks at Shelter Cove! Duration 3 hours About From June to August we offer a weekly cruise to watch the fireworks at Shelter Cove. You’ll have a front row seat to see the magic aboard! This three hour cruise is only on Tuesdays in...

Three Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$150.00 - $675.00

Electric Bike Rental Duration 21 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all without...

Stand Up Paddle Boarding Tour

Hilton Head Island Recreation Association

Book online
$40.00

duration: 1.5 hours meeting_point: Rowing and Sailing Center description: Your 1.5hr stand up paddle board trip will explore the marshes of Skull Creek. An educational Lowcountry experience learning and working with the tides, oysters, and...

Luxury Pontoon Rental
Book online
$315.00 - $815.00

This pontoon offers spacious dual captain's chairs, comfortable sofa-style seating and enhanced style. Can accommodate up to 12 passengers. Includes: -Cooler -Bluetooth Radio

13 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$95.99 - $191.99

13 Day Rental Rates: - 16” Kids Beach Bike: $90.99 - 20” Kids Beach Bike $90.99 - 24” Youth Beach Bike: 90.99 - 26” Bike w/ Child Seat: $105.99 - 26” Mens Beach Bike: $90.99 - 26” Unisex Beach Bike: $90.99 - 12" Balance Bike: $90.99 ...

Fireworks Cruise

Island Time Charters

Book online
$425.00

Duration 2 Hours About This Fireworks Cruise provides a front row seat to one of our Island's most popular events! Enjoy the sunset while dolphin watching and taking in the beauty of the salt marsh ecosystem then stay on board with the best...

Lowcountry Curated: Hilton Head E-bike and Picnic

duration: 4 Hours meeting_point: 50 Shelter Cove Lane, Hilton Head, SC 29928 min_age: 16 group_size: 4/10 pricing: $198 description: Explore Hilton Head’s storied past on a guided e-bike tour to Mitchelville, the nation’s first freedmen’s...

Life Under the Sea

Coastal Discovery Museum Hilton Head

Book online
$5.00

There is a magical world full of fascinating creatures under the sea! Join knowledgeable Museum staff and volunteers in the Discovery Lab to explore, touch, create, play, and learn more about ocean life. Who lives in those shells? What does a crab's...

Hilton Head to Daufuskie Island

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: 18 Simmons Road Hilton Head Island, SC description: Hilton Head -> Daufuskie Island One Way...

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