Hilton Head, SC Vacations

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Featured Vacation Rentals

Fully Renovated Hilton Head Vacation Ren...
4.7
(17)

Savor this impressive villa located within Turnberry Village! With one of the best locations in the community, this completely refreshed villa offers striking vistas of a calming lagoon and fountain, and is located directly across from the community...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Marriott SurfWatch Resort Condo in Hilto...

Located along a handsome stretch of shoreline on fashionable Hilton Head Island, this appealing resort's oceanside setting, comfortable accommodations and fine amenities are sure to impress. With its private oceanfront location, Marriott's...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Sunny Ocean Club Condo | Pool & Private ...
4.7
(32)

Ocean Club 35Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located just steps from the waves in the beachfront Ocean Club complex, this 2BR/2BA two-story...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Cozy condo with tennis, pool, beach acce...
4.9
(7)

Forest Beach Villas 107Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make memories that will last a lifetime at this first-floor condo in South Forest Beach...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Beautiful Recently Updated Tree Top Vill...
4.7
(51)

Treetops 5402Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the Treetop Villas community in the beautiful South Forest Beach neighborhood, this...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Redesigned Ground-Floor Villa with Pools...

Fiddlers Cove 11COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your ideal island hideaway awaits at this newly redesigned 2BR/2BA ground-floor villa at...

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

Hilton Head Tours & Activities

Baby Gear Rental Package • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$410.00 - $560.00

Don't pack it, Rent it! Affordable Baby Gear packages to meet your vacation needs! Duration 14 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Surfing Lessons

Hilton Head Island Recreation Association

Book online
$100.00

duration: 1 hour & 15 minutes meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 min_age: 5 group_size: Up to 10 people description: Learn to Surf in the safe and warm waters of Hilton Head Island! Our safe...

Yoga on the Water – Sunrise Flow Aboard Bonjour

duration: 90 Minutes meeting_point: Broad Creek Marina, 18 Simmons Road description: Start your morning with peace, presence, and purpose — join us for a 90-minute yoga flow and meditation aboard Bonjour, our serene 36-ft catamaran, every Tuesday...

Kayak Rentals (Please call if unsure about booking a Guided Tour versus a Kayak Rental)

Kayak unguided if you have kayaking experience. We will go over the area with you, tell you about the dolphins favorite spots to hang out and answer any questions that a you have before departure. Of course our guided tours are available as well if...

Classic Splatter Session

Color Me Greenville

Book online
$30.00

duration: 45 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 group_size: 6 Max description: 45 minutes of splatter painting on a 11x14 basic canvas board using our paints! Customization options available! 1 to...

Lessons

Daufuskie Marsh Tacky Society

Book online
$45.00 - $75.00

Duration 1 hour About We offer a handful of lesson options to meet the needs of a wide variety of individuals looking to grow their skills around horses on the ground and in the saddle. Appropriate for ages 7+ through adult, who are total...

Bike Rental • Two Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $80.00

Rent Bikes and Gear Accessories for your vacation! Duration 2 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Guided Kayak Tour

Island Head- Hilton Head Harbor

Book online
$40.00 - $75.00

*Paddle the Low Country!* ___________________________________ Rates **Kayak:** $40 **Tandem Kayak:** $75 *All Ages* ___________________________________ Duration 1 hour and 30 minutes ___________________________________ About Come...

Dolphin & Nature Tour

Dolphin and Nature Tours

Book online
$5.95 - $31.95

Rates - Adults (Ages 12 and up) - $31.95 - Child (Ages 2-11) - $16.95 - Wee One (Children under 2) - $5.95 ___________________________________ Duration 1.5 Hours ___________________________________ The best dolphin tour on Hilton Head...

Shared / Family Shell Hunt & Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$49.75

duration: 1.75 to 2 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. group_size: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

Yellow Moke Rental

Carolina Rides

Book online
$250.00 - $5,000.00

The best way to travel around Hilton Head! Duration Daily & Multi-Day Rentals About Leave your family car behind and rent a Moke for the day, weekend, or your entire vacation! Experience the open air while shopping, visiting friends or just...

Backwater Adventure Day

May River Excursions

Book online
$525.00 - $825.00

Rate -3 hrs- $525 - 4 hrs- $625 - 5 hrs- $725 - 6 hrs- $825 ___________ About - Take a private custom excursion through the backwater ways and marshes around the barrier islands of the Lowcountry with a local captain. Choose from inshore...

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