Hilton Head, SC Vacations

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Featured Vacation Rentals

3 Shore Crest, Chefs Kitchen, Free Golf,...

3 Shore Crest Lane, Hilton Head Island. Luxury awaits in this bespoke-constructed 5-bedroom home in Burkes Beach, just a 5-min. walk to the beach and adjacent to Chaplin Park. Appreciate high-end finishes, a chef's kitchen, sunroom, covered deck...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Dreamy island condo with balcony, shared...

HH Beach & Tennis 212COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get ready to call Hilton Head Island home for a little while when you book a stay at...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Walk to Hilton Head Island Beach: Villa ...

Dive into relaxation at this 2-bedroom, 2.5-bathroom villa on Hilton Head Island! Ideal for snowbirds, this chic coastal vacation rental is located less than a mile from Coligny Beach Park and just a few mins. from golfing, stores, and eateries...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
French Country home on Golf Course with ...

Coastal CharmOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on the 1st Tee of the Clipper Course in Shipyard Plantation, this appealing French...

  • Hilton Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Inviting condo with pool, balcony, beach...

Plantation Club 448Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'For a pristine coastal hideaway full of appeal and style, discover this striking condo near...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Oceanview Retreat! Beautifully Remodeled...
4.7
(17)

Managed professionally by Vacation Time of Hilton Head, our oceanfront complex is appealingly booked directly through our website.Oceanfront, completely Renovated Hilton Head Beach Villa 24!!Exciting News: Our Stunning New Swimming Pool is Now...

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

Hilton Head Tours & Activities

PB Family Ski Day
Book online
$245.00 - $1,290.00

description: *Certified instructors will show you the ropes on this 2 1/2 hour program! Ski, tube, wakeboard and kneeboard.* _________ About Cruise from Palmetto Bluff back to our favorite ski grounds and learn how to water-ski, wakeboard...

Cocktails & Camellias

Coastal Discovery Museum Hilton Head

Book online
$150.00

duration: 3 hours meeting_point: 70 Honey Horn Dr, Hilton Head Island, SC min_age: 21 accessibility: Wheelchair accessible description: Immerse yourself in the beauty of the Lowcountry at *Cocktails & Camellias*, an elegant evening set against the...

Discovery Flight

Hilton Head Helicopter Tours

Book online
$400.00

duration: 1 Hour (30 minutes flight time and 30 minutes ground) meeting_point: 38 Gateway cirle HHI,SC 29926 min_age: 16 description: Get ready for the adventure of a lifetime with a Discovery Flight! This hands-on experience gives you the...

???? Cook at Home Classic Lowcountry Boil

duration: 10 minute pick up meeting_point: 37 New Orleans Road Suite B, Hilton Head Island, SC pricing: Base price is $59.99 for 2 people. Each additional person is $25.99. description: Our Lowcountry Boil bucket comes packed with everything you...

Tubing and Dolphin - 12 max

meeting_point: Hilton Head Island, SC description: Family Fun With Nature, Tubing and Exploring! --- Join us for a boating and tubing tour through the Lowcountry waters! Watch for birds and dolphin through the salt marsh ecosystem and get behind...

Beachcombing on

Blue Pearl Marine Dolphin Tours

Book online
$65.00 - $225.00

Call 843-683-0731 to book today! Rates 1-3 passengers $225 Each additional passenger $65 6 person max ___________________________________ Duration 3 Hours ___________________________________ About Disappearing island is Located between...

Mini Boat Disappearing Island Tour

Lowcountry Watersports

Book online
$249.00

duration: 2 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 group_size: 2, 3 or 4 per mini...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

description: Explore Coligny and its culinary offerings! Duration 2 hours and 30 minutes What's Included: - All tastings (amounts to a whole meal) - A fun and informative tour of the Coligny area About We will meet at our first location...

Private Lesson with Sean Ritter

Palmetto Dunes Golf Academy

Book online
$90.00 - $450.00

About Sean Ritter Sean Ritter graduated from the Professional Golfers Career College in Bluffton, SC with honors and is originally from Charlotte, NC. After his graduation, Sean was further mentored and tutored under the award-winning Palmetto...

Tuesday Fireworks and Sunset Sport Crabbing Adventure

Join us for a Seasonal Summertime Firework and Sunset Sport Crabbing Adventure Duration 2.5 hours About Our Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on...

19' Stingray Rental

H2O Sports

Book online
$325.00 - $750.00

duration: 2-6 hour rentals cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Boat holds 6...

One Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$43.99 - $59.99

description: Single Kayak 1 Hour Rental: $33.99 ________________________________ Double Kayaks or Canoes 1 Hour Rental: $46.99 __________ Triple Canoe 1 Hour Rental: $59.99

Find your perfect Hilton Head

Fishing Charter

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