Hilton Head, SC Vacations

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Featured Vacation Rentals

Fantastic Fazio Villa with Golf Course V...

Come appreciate this huge golf course villa with room for the family to spread out! Walking through the villa, you'll soon understand that comfort was made high priority while still maintaining a modern concept. The living room and all bedrooms...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Relaxing condo with golf course views, p...

Summary:Hickory Cove 39The Space:Located in the sought-after Palmetto Dunes, this impressive pool-view townhome is the ideal home base for your Hilton Head Island hideaway. The bright, sun-filled living area opens onto a private, furnished deck with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Panoramic Oceanfront Views Abound! Two B...

As soon as you enter this 5th floor Hilton Head oceanfront villa you'll be greeted by sweeping expansive vistas of the Atlantic Ocean. The entire villa has been refreshed with new wood floor. The Kitchen is to the left as you enter and comes...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Oceanfront condo with a washer, dryer, c...

Summary:Shorewood 311The Space:At this Hilton Head condo, you can take a dip in the seasonally-heated, shared pool, walk on the sand and splash in the ocean, or soak your cares away in the relaxing hot tub - whichever you chose, relaxation is...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront condo with pools, hot tubs, W...

Summary:Seacrest 1101The Space:Welcome to SeaCrest Villa 1101! The SeaCrest Villas is an oceanfront resort located in the ideal location on Hilton Head Island, directly across the street from Coligny Plaza. Conveniently located on the first floor...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Beachfront getaway with WiFi, pools, hot...

Summary:Island Club 5101The Space:Heed the call of the beach at this ground-floor, oceanfront condo in the calming, 27-acre Island Club of Hilton Head! Outside, your furnished patio is ideal for morning coffee – courtesy of the Keurig and supplied...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9

Hilton Head Tours & Activities

Weekday 9:30am-3:30pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekday - Golf Cart Rental 9:30am - 3:30pm *Must have valid Driver's License to rent a cart.*

Water Bottle

Historic Mitchelville Freedom Park

Book online
$1.00

pricing: $1 description: Water Bottle

Donuts with Santa Cruise

Vagabond Cruise

Book online
$24.95 - $44.95

duration: 60 Minutes cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 accessibility: Not Wheelchair Accessible description: **Donuts with Santa Cruise** Experience the joy of the...

Beach Bum

Hilton Head Helicopter Tours

Book online
$109.00

duration: 20 miles description: This helicopter tour follows Hilton Head’s most active stretch of beaches to Coligny Beach, the island’s popular beach park. Pilots keep the flight low along the shoreline for close-up views of surf and potential...

Lessons

Daufuskie Marsh Tacky Society

Book online
$45.00 - $75.00

meeting_point: 281 Old Haig Point Rd description: 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...

Private Afternoon Sail and dolphin watch on Seas The Moment - newest vessel

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we...

Kayak Club

Hilton Head Outfitters - Bike Rental

Book online
$300.00 - $450.00

description: Valid through 2026 calendar year Unlimited kayak rentals for membership holder and 50% off rentals for additional guests on booking. Applies to One Hour Kayak or Canoe Rental, 1.5 Hour Kayak or Canoe Rental, and Two Hour Kayak or...

Family Ski Day

Outside

Book online
$135.00 - $1,065.00

meeting_point: Hilton Head Island, SC description: Get behind a boat with Outside Hilton Head for some high-intensity fun! --- Description Hilton Head’s waterways are perfect for getting all ages out on tubes, skis, wakeboards, and...

Eight Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$70.99 - $141.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Cap
Cap

Historic Mitchelville Freedom Park

Book online
$25.00

pricing: $25 description: Cap

Paint the Pony - Montage Guests
Book online
$170.00

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

Guided Kayak Tour

Island Head- Hilton Head Harbor

Book online
$40.00 - $75.00

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

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