Hilton Head, SC Vacations

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Featured Vacation Rentals

Spacious Villa with Shared Pool, Hot tub...

Island Club 113Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Visit this cavernous Island Club villa to savor an adult calming pool and hot tub, shared kid's...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunset Rentals | St. Andrews 1880 | Dog ...

This 2nd floor, 2 bedroom, 2 bath townhouse in St. Andrews Commons is a opulent hideaway in the middle of the elegant Palmetto Dunes plantation on Hilton Head Island. If you’re looking for pet-friendly Hilton Head vacation villas, St. Andrews 1880...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Spacious condo with patio, pool, walking...

Hilton Head Cabanas 3Our 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 Hilton Head, SC! This gorgeous condo, located in the...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Sunset Rentals | Evian 103 | Dog Friendl...

This roomy 3 bedroom, 3.5-bath townhouse villa is located in the trendy Evian section of Shipyard. The villa has a great golf course view from many windows and the cavernous back patio. The patio is equipped with a table for 6. By day, the living...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Kitchen updated,Rates include cleaning

Our 800 square foot, second-floor Condominium is refreshed and elegantly and elegantly refreshed with reasonable rental fee. It is a few steps to one of the two pools, two of the ten complimentary Har-Tru tennis courts, two racket ball courts, two...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Comfy Condo with Shared Pool, Tennis Cou...
4.2
(18)

Lake Forest 3361Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This secluded home is the ideal destination for families and groups of friends planning their...

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

Hilton Head Tours & Activities

Awendaw Creek - Intracoastal Waterway Kayak Tour
Book online
$52.00 - $118.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Flyboard 30 Minute

Carolina Hydrofly

Book online
$129.00

30 Minute Flyboard Pro Series Experience About Each guest will have 20 minutes of flight time and 10 minutes of instruction time. If you would like to book for more than one person, then please process one booking per person by selecting the...

Sunset Beach Photography

Island Life HH Photography

Book online
$195.00 - $745.00

Capture Sunset Memories To Last A Lifetime Duration Up to 60 minutes, with most shoots lasting about 45 minutes About Want to commemorate a special life moment, celebrate a new addition to your family, or just capture the family fun...

Summer Fireworks and Kayaking Dolphin Nature Tour

Kayaking Tour and Shelter Cove Fireworks Display! Duration 2.5 Hours *Please arrive 30 minutes prior to your scheduled tour time* On Tuesday evenings in the summer months our regular 2 hour evening sunset tour is followed by the Shelter Cove...

Baby Gear Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $100.00

duration: 1 Day cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental drop...

Hilton Head Yacht - Day Cruise

Hilton Head Yacht Charter Company

Top Shelf Yacht Charters are all about you. From adventure to anniversaries, relaxing to proposing, there's nothing we can't do for you during your cruise! Imagine your own floating resort! Experience 80 feet of pure opulence aboard Top Shelf. Our...

Strand Feeding Tour

Cross Island Cruises

Book online
$299.00

Join your Captain on a private excursion in the back waters of the salt marsh as we look for dolphins strand feeding. Duration 2 Hours Rates **Private Charter:** $299 About Get up close and personal watching these beautiful creatures...

Kayak Tour

Lowcountry Watersports

Book online
$45.00

duration: 1.5 Hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 pricing: Rates Single Kayak...

The Standard

Island Segway

Book online
$79.00

Explore Hilton Head Island by Land! Duration 1.5 Hours About Explore Hilton Head Island in style with this Island Segway tour! This 1.5 hour tour cruises down charming bike paths and boardwalks through Three beautiful parks to Hilton...

Shark Tooth Island Excursion

duration: 4 Hours meeting_point: Shelter Cove Marina (next to Ela's) pricing: $95/person + 20% gratuity description: *Hunt for Treasures of the Sea!* Enjoy a scenic boat ride from Hilton Head to Savannah, where you will step off onto islands to...

Two Day Schools

Palmetto Dunes Golf Academy

Book online
$750.00

Duration & Rates - 2 Days, 3 hours of instruction per day - $750 per student About The small group 4:1 student:teacher ratio promotes important quality attention. Skill levels can be mixed and the instructor is able to meet the unique needs of...

One Week Electric Bike Rental
Book online
$250.00

duration: 7 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

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