Hilton Head, SC Vacations

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Featured Vacation Rentals

Coastal condo w/ a shared pool - steps t...
3.8
(8)

Breakers 215Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in the spectacular ocean vistas from the comfort of your balcony or inside from your living...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Snowbird-friendly condo near golf with p...

St Andrews Common 1759Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Centrally located on Hilton Head Island, this coastal getaway has everything needed for...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Quiet Hilton Head Getaway with WiFi, Poo...
4.7
(21)

Island Club 1404Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This two-bedroom, two-bath Island Club condo is the right one to choose for family getaways...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Stunning, coastal chic two bedroom, two ...

Stunning coastal chic two bedroom two bathroom villa! Come and relax in this newly modernized and decorated 1st floor villa in Palmetto Dunes Oceanfront Resort within the Centre Court complex. Savor peaceful mornings on the porch overlooking the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Cute condo just steps from the beach & n...
4.3
(39)

Moorings 09Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Cavernous and bright, this adorable villa is located in the heart of Palmetto Dunes. Whether...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Updated Hilton Head Island Vacation Rent...
5.0
(1)

This sizable Water Oak villa is now on the rental market and has multiple new updates! The Kitchen comes entirely-equipped with the amenities of home while boasting all stainless steel appliances, bespoke cabinetry and granite countertops. The...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Two Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$380.00

Duration 2 Hours ___________________________________ About Learn about fishing, catch sharks and other species and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you will catch....

Six Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

Electric Bike Rental Duration 6 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...

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy beverages of...

Two Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$53.99 - $81.99

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

Parasailing

Island Head- Hilton Head Harbor

Book online
$49.00 - $999.00

*High Flying Family-Fun Parasail over Hilton Head.* ___________________________________ Rates **Flyer (Ages 6+):** $89 **Observer (All Ages):** $39.99 ___________________________________ Duration 1 hour and 30...

Stand Up Paddle Board Rentals

Hilton Head Island Recreation Association

Book online
$50.00 - $165.00

duration: 2-8 Hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 description: Explore the scenic waterways of Hilton Head with our Stand Up Paddle Board (SUP) rentals! Whether you're paddling through calm...

Sunset Celebration Dolphin Cruise

Island Head - Broad Creek

Book online
$10.00 - $49.99

duration: 90 Minutes cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: Enjoy all of the beauty the low...

Flyboard 20 Minute

Carolina Hydrofly

Book online
$99.00

20 Minute Flyboard Pro Series Experience What's Included? 15 Min Flight Time. Includes 10 minutes of instruction time, fuel, life jacket, wetsuit, and helmet We advise everyone to arrive at least 30 minutes before your start time. If...

Two Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$40.00 - $200.00

Rent with us! Duration 14 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and attachments

Daufuskie Island Beach Combing

Island Life Rentals and Tours

Book online
$65.00 - $780.00

Daufuskie Island Beach Combing Duration 3 hours About Let our experienced captains love for the waterways guide you and your loved ones on the perfect experience you’re sure to never forget. Just a short distance from civilization lies a...

Director's Walk

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $25.00

*Visit Honey Horn with the Museum's Director.* ___________________________________ Duration 1.5 Hours ___________________________________ About Walk the shell path and Nan Lloyd Trail with the Museum director and discover some of the...

Baby Gear Rental Package • Two Days

Lowsea Bike, Beach and Baby Rental

Book online
$165.00 - $210.00

Don't pack it, Rent it! Affordable Baby Gear packages to meet your vacation needs! Duration 48 Hours About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

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