Hilton Head, SC Vacations

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Featured Vacation Rentals

Courtside Villas Retreat w/pools & tenni...

Courtside 83Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your dream Hilton Head escape awaits at this 2BR/2.5BA townhome! Located in the Courtside Villas...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Two Bedroom First Floor Single-Level Vil...

Escape to this gorgeous, ground-level St. Andrews villa, where you'll savor a calming hideaway in the heart of Palmetto Dunes Oceanfront Resort. This roomy, single-level floor plan offers a ideal blend of comfort, style, and convenience.The entirely...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Oceanfront resort condo with WiFi, balco...

Oceanside Villas II 289Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to heaven at this welcoming condo in Hilton Head, SC, where memorable beach...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
2 bedroom villa located in Harbourtown

Ideal vacation villa for families, golfers, and the avid beach goers! Heritage Villas is located in the beautiful, gated community of Sea Pines Plantation, offering three professional golf courses, one of which is Harbour Town, home of the Heritage...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Charming 2-Bedroom Vacation Rental Overl...

Escape to your ideal hideaway in this delightfully appointed 2-bedroom Hilton Head vacation rental. Located in a serene setting, this getaway features a private deck that overlooks a lagoon, complete with a relaxing fountain that enhances the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
5 Camellia St- Beach Vacation! 3 Bedroom...

New to the Vacation Rental Market! Attractively remodeled 3 Bedroom 3 Bath private home just 3 blocks to the beach! Each bedroom has an ensuite bathroom. The home features 2 master suites with king beds, and 3rd bedroom has 2 queen beds.Grab your...

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

Hilton Head Tours & Activities

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...

Happy Hour Cruise

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane pricing: $75 per adult (adults only) description: Happy Hour Cruise aboard Ohana ???? Unwind on the water with our adults-only Happy Hour Cruise in Hilton Head...

Three Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$480.00

description: Duration 3 Hours ___________________________________ About Catch sharks, other species, might catch some nice fish and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you...

Workshops

Coastal Discovery Museum Hilton Head

Book online
$5.00 - $35.00

duration: varies cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: Join us for a dynamic series of hands-on, creative workshops designed...

SCM Lowcountry Boil Dinner Cruise

duration: 2 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head pricing: Adults: $145 Children 10yr-2yr: $99 Under 2: $20 description: Set sail for an unforgettable evening on the water with Outside Hilton Head’s Lowcountry Boil Dinner Cruise...

Four Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

description: Four Day Rental Rates: - 16” Kids Beach Bike: $64.99 - 20” Kids Beach Bike $64.99 - 24” Youth Beach Bike: $64.99 - 26” Bike w/ Child Seat: $79.99 - 26” Mens Beach Bike: $64.99 - 26” Unisex Beach Bike: $64.99 - 12" Balance...

Beach Gear Rental • Six Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Everything you need for a fun and comfortable day at the beach! Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than 5PM. Duration 6 Days About - Free delivery...

PB Outside Foundation Cruise

meeting_point: Palmetto Bluff description: The Outside Foundation and Palmetto Bluff are partnering to preserve the South Wilson Bluff, utilizing oyster shells recycled from Palmetto Bluff Club restaurants. To learn more about this program and other...

Canoe Rental

Wateree Marina

Book online
$25.00 - $50.00

description: Canoe Rentals What to Bring - Valid Driver's License - Major Credit Card

Four Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$220.00 - $524.00

description: Enjoy miles and miles of scenic bike paths Duration 4 Weeks About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

Rocky Land RC

Red Maple Event

Book online
$5.00

duration: 5 minutes meeting_point: Saluda Shoals Park min_age: 6 description: Customer will be able to drive a RC Crawler for 5 minutes on the Mobile Crawler Course what_is_included: Course Rules: -Stay in the course boundaries -No wreck less...

Solaris - Afternoon Sightseeing Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Customize a luxurious charter aboard Solaris today! **Our private charters accommodate seven to ten passengers, ensuring an intimate and...

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