Hilton Head, SC Vacations

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Featured Vacation Rentals

Family Friendly Villa near the Beach, Pa...

Summary:Shipmaster 1003The Space:**This property is completely refreshed and gorgeously done. Pictures coming soon**Located in the heart of Shipyard resort area this handsome condo offers a ideal getaway for those looking to savor the best of the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Updated Condo with Fast WiFi, Shared Poo...

Summary:Sea Side Villas II 149The Space:Get a taste of island bliss in this beautiful condo in the heart of all the action here on Hilton Head Island! Whether you have come to lounge by the shining shared pool, sip a coffee on the private balcony...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
2516 Windsor Place II- Fully Renovated C...

Welcome to this 5th floor Windsor condominium! The Kitchen has quartz countertops and is entirely-equipped with everything you'll need to prepare for your family. There is Kitchen bar seating for two as well. The Kitchen looks out to the Dining...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Captains Quarters w/ a Shelter Cove Mari...

Welcome to our handsome condo located in The Shelter Cove Marina. Come visit our condo and feel like you are at Home with our charming vistas of the Marina. The vistas and the quietness are calming and serene. Our gated complex has a freshly...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 2
Airy, lagoon-view condo with pool, hot t...

Summary:Island Club 107The Space:This comfortable modern condo at the Island Club is the ideal destination when you're in the mood for a calming hideaway along a breathtaking waterfront. The welcoming design is ideal for kicking back and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Sandcastle by the Sea - 3 blocks to beac...

Summary:Sandcastle 97The Space:Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA getaway that promises an elevated vacation experience. This brand-new home features high-end finishes paired with extraordinary...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18

Hilton Head Tours & Activities

Beach Wheelchair

Hilton Head Outfitters - Bike Rental

Book online
$65.00 - $299.00

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...

Historic River Excursion

May River Excursions

Book online
$40.00 - $50.00

description: *Learn more about Bluffton through our scenic trip!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ Duration 1.5...

Fishing Charter - Kahuna

Native Son Adventures

Book online
$365.00 - $1,260.00

description: Duration 3 to 8 Hours About In-Shore and Near-Shore Fishing. The most stable adventure vessel on Hilton Head Island! The 26 foot Glacier Bay catamaran is the cream of the crop! He does it all, so let’s go have some fun...

Paella Dinner

Kennington Family Winery

Book online
$95.00

duration: 2 Hours min_age: 21 group_size: Maximum 30 Guests description: **Join us for a Paella Dinner, catered by the highly esteemed Chef Daniel Lopez!** Choose between chicken paella or authentic Spanish paella with muscles and shrimp. Glass of...

3 Hour Private Spring Jocassee Boat Tour

description: Private 3hr Spring Tour on Beautiful Lake Jocassee! Rates - Private Charter (includes up to 6 people): $350 ***$50 for each additional person (up to 10 total passengers)*** About Boat Tour includes all major waterfalls...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

description: See dolphins in their natural habitat! Duration 2 hours About The Lowcountry is home to several pods of Atlantic Bottlenose Dolphins. Join us for a 2 hour cruise to see them in their natural habitat and take in the beauty...

Hilton Head Dolphin Tours (2 Hours)

Hilton Head Boat Charters

Book online
$340.00 - $799.00

duration: 2 Hours cancellation_summary: We need at least 72 hours notice for a full refund. meeting_point: 43 Jenkins Island Rd, Hilton Head Island, SC 29926 group_size: Up to 20 People description: The best 2-hour charter on the island Ride in...

One Week Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Rate 7 Day Rental: $149.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration One Week (7...

Eight Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$1,200.00

description: Duration 8 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, King Mackerel, Cobia, Triple Tail, Sharks! (Species Depend On Season, Tide & Weather) *This...

Tuesday night Firework Sailings

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

description: About Night time Fire Work sailing charter! More info **Pricing:** • 1-6 people: $600.00 and $100 for each additional person up to 14. ($1,400) • 15-20 people is a flat $1,500.00

Palmetto Bluff

Flip Flop Charters

Book online
$625.00 - $750.00

description: Beautiful Scenery Duration - 3 hours - 4 hours About Nestled on the scenic May River is Palmetto Bluff, an idyllic community on 20,000 acres. Within the community is an extensive nature preserve, private residences, a hotel...

Daufuskie Island Beach Combing

Island Life Rentals and Tours

Book online
$65.00 - $780.00

duration: 3 Hours description: Daufuskie Island Beach Combing About Let our experienced captains love for the waterways guide you and your loved ones on the perfect experience you’re sure to never forget. Just a short distance from...

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