Hilton Head, SC Vacations

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Featured Vacation Rentals

89 The Moorings: 2  BR, 3  BA Villa in H...

Welcome to this charmingly appointed 2-bedroom, 3-bathroom condo located in The Moorings community within Palmetto Dunes Oceanfront Resort on Hilton Head Island. Ideally located near the beach and The Dunes House beachfront bar and grille, this...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Penthouse living at Shelter Cove Marina ...

Summary:Harbourside PenthouseThe Space:Feel the luxury of penthouse living at this all-suite 3BR/3BA condo with a covered balcony overlooking the harbor. Your fourth-floor hideaway features a impressive kitchen, spiral staircase, and a lavish master...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Charming Condo 1 block from Coligny Plaz...

Summary:Sands Village B3AThe Space:This condo places you right in the heart of laid-back Lowcountry living, just a block from Coligny Beach Park, Coligny Plaza, and the Adventure Playground. Appreciate painless access to a wide variety of eateries...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
SeaPines-Villa 488-Walk to the Beach Clu...

SeaPines is a very special place and 488 P. Club has a great central location---very close to the on-site pool and elegant white sand beaches. Your whole group will savor the cavernous layout of this well thought out 3 bedroom villa just 1/2 mile...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Stunning Oceanfront property, Just Steps...

Welcome to your ideal home base for a Hilton Head hideaway, whether it’s your first or your next! Located in an unbeatable oceanfront complex, you’ll be just mins. from the beach, with the complex pool conveniently located right downstairs. For...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
7816 Centre Court has scenic wooded and ...

This private second floor villa has breathtaking wooded and lagoon vistas. This villa opens into a entirely equipped kitchen with bar seating for 2. The kitchen overlooks the dining room, which has a table with 4 chairs and a bench seat...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Daufuskie Trip

Flip Flop Charters

Book online
$725.00

description: Come explore the island! Duration 3 hours About Tucked between Hilton Head and Savannah is Daufuskie Island. With no bridges it is only accessible by boat. On the island are restaurants, golf courses, a distillery, and plenty of...

Baby Gear Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$30.00 - $350.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 14 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean...

3 Day Rental

Island Life Rentals and Tours

Book online
$21.00 - $140.00

duration: 3 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Busy Bees Workshop

Coastal Discovery Museum Hilton Head

Book online
$20.00

duration: 1 hour cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 min_age...

Twelve Day Electric Bike Rental

duration: 12 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Mixology and Tapas Tour

Food Tours Hilton Head

Book online
$79.95

description: *The Island's Tastiest Experience!* Duration 2 hours and 30 minutes What's Included: - All drinks at each stop - Tasty tapas at each stop About Take a bite out of the island! Do something new, fun and exciting! If you...

Hilton Head Yacht - Dinner Cruise

Salt Shaker Charter LLC

Book online
$4,900.00 - $8,000.00

duration: 4 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: An Evening Aboard Salt Shaker: Gourmet Dining Meets Sunset Serenity! Aboard Salt Shaker, every moment is...

Disappearing Island Dolphin Tour

Lowcountry Watersports

Book online
$10.00 - $49.99

duration: 2 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 1 max_age: 99 group_size: Maximum 48...

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...

Private Inshore Charter Fishing aboard Hobo

duration: 3 hours cancellation_summary: 48 hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way. Please proceed down to the first dosk on the right side of the marina. group_size: Licensed for up to 16 passengers; rate includes 6...

Deck the Porch

Brice Herndon Draft Horse and Carriage Company

Book online
$100.00

description: Ride in our Vis-a-vis Carriage A more intimate and private setting with your own personal horse and driver. Enjoy private time with your family or make it a couple's adventure strolling through the Front Porch of the Lowcountry! ...

Six Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$800.00

description: Duration 6 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, Cobia, Sharks! 6hrs gives us time to target a couple different species, more fishing time...

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