Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

This fully renovated Hilton Head Vacatio...

This charmingly remodeled Hilton Head vacation rental offers a extravagant coastal escape. It is located on the 4th floor with elevator access for painless arrival. The roomy living room features a huge mounted flat-screen TV and direct access to a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
SeaPines, Walk to Beach Club, Direct gol...

Private location yet very close to the best white sand beaches at the SeaPines Beach Club, this cavernous, sunny villa promises a memorable HHI vacation. Your family will adore the handsome new kitchen remodeling finished in 2025-charming cabinets...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stunning Hilton Head Island Vacation Ren...

Discover the many updates that have taken place in this elegant Turnberry Village villa in Hilton Head Island! The open-concept living space is filled with natural light and features vaulted ceilings, creating a bright and airy ambiance. The kitchen...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Newly Renovated Villa at The Spa on Port...

Summary:Spa on Port Royal Sound 3121The Space:Don't miss out on this hidden treasure! Located in The Spa on Port Royal Sound, this freshly modernized 2BR villa features a secluded, gated setting with private access to one of the quietest beaches on...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Condo 1 block from Coligny Plaza with on...

Summary:Sands Village A2CThe Space:Located in the heart of Hilton Head, SC, this beautiful villa is just blocks away from the pristine beaches of the island. Located only one block from Coligny Plaza, the vibrant hub of the area, you'll have simple...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 5
Amazing pools, hot tub, and oceanfront v...

Summary:Villamare 3425The Space:Savor your breakfast and coffee from your shaded balcony while taking in the vibrant sunrise at this Villamare condo. The view from the fourth floor also overlooks the outdoor pool, beach, and picnic area, which are...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Tubing and Dolphin - 6 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...

Raffle - 2025 Sweetgrass Basket

Coastal Discovery Museum

Book online
$10.00

duration: 1/6/2025 - 1/31/2025 meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 pricing: $10 each description: Coastal Discovery Museum's Sweetgrass Basket raffle to be drawn at the 2025 Cocktails & Camellias event at 7:30 p.m. on...

Gift Card

Wateree Marina

description: Purchase the perfect gift: a gift card with a value of your choosing!

Memberships

Coastal Discovery Museum

Book online
$100.00 - $1,000.00

description: All Members Receive Invitations to members-only seasonal programs Invitations to exhibit openings Advanced notice of upcoming events and lectures Monthly membership bulletin Discounts in the Museum Store $100 Supporting...

Alligator & Wildlife Tours
Book online
$15.00 - $350.00

duration: 1 hour cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Fish Island Sea Pines Forest Preserve group_size: Up to 12 passengers description: Join us on a 1-hour guided tour of the...

Archery Tag

Jeffery Archery

Book online
$225.00 - $375.00

duration: 1 or 2 Hour Parties description: Experience the thrill of dodgeball combined with archery in our action-packed Archery Tag events. Using lightweight bows, foam-tipped arrows, and inflatable bunkers, players compete in fast-paced team games...

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...

11 Day Rental

Island Life Rentals and Tours

Book online
$45.00 - $315.00

duration: 11 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...

Lowcountry Seafood Experience

May River Excursions

Book online
$135.00

meeting_point: Hudson's Seafood Restaurant description: Rate - $135 per person includes boat excursion as well as a meal and one beverage __________ Duration - 2 Hour Boat Excursion with meal afterwards at Hudson's ____________ About ...

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! ...

Two Hour Dolphin Nature Cruise

Hilton Head Island Tours

Book online
$250.00

description: *Enjoy your 2 Hour Dolphin Nature Cruise!* ___________________________________ Rates **Private Charter** - $250.00 ***All ages welcome! | Maximum of 1200 lbs*** ___________________________________ About your Fishing Trip: ...

Fishing Charter

Reel Native Fishing Charters

Book online
$350.00 - $1,150.00

description: Let's get out on the water and makes some memories that will last a lifetime! Rates & Duration - 2 Hour Charter • $350 - 3 Hour Charter • $475 - 4 Hour Charter • $575 - 5 Hour Charter • $700 - 6 Hour Charter • $875 - 8...

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