Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

End-unit, 3rd-floor condo near beach wit...

Fiddlers Cove 16LOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bright and welcoming, this third-floor, end-unit condo in the Fiddler’s Cove complex is the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stunning and bright condo in The Sea Pin...

Plantation Club 545Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend the day calming in this striking and bright condo in The Sea Pines Plantation...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Spacious townhome w/ balcony, desk + mon...

Shipmaster 1702Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head Island, this roomy and inviting 2 story townhome in...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Cheerful condo with shared pool, close t...

Windward Village 117Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your delightfully decorated condo in the heart of Hilton Head, SC, located...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Palmetto Dunes Condo with Golf Course Vi...

Summary:Fazio 23The Space:Golf Course Vistas & Updated Comfort in the Heart of Palmetto DunesOverlooking the spectacular Fazio Golf Course, this cavernous, newly refreshed townhouse is the ideal home base for your Hilton Head Island hideaway...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Updated condo in beachfront complex with...

Carolina Beach Club 427 / PineappleOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Soak up the sun and savor a ideal Hilton Head vacation from this modern...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

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...

Bar Crawl

Flip Flop Charters

Book online
$625.00 - $750.00

description: Beautiful Scenery Duration - 3 hours - 4 hours About If you’re looking for some adult fun, there is no shortage of waterfront bars in our area. We’d love to take you to some of our favorites or let you pick the itinerary....

Nine Day Bike Rental

Wheelz of Hilton Head

Book online
$60.00 - $120.00

description: Nine Day Bike Rental Rates Duration 9 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Lowcountry Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

duration: 10–15 minutes cancellation_summary: Full refund if weather forces cancellation and no mutually available reschedule; otherwise weather-dependent rescheduling. meeting_point: Jarvis Creek Park, 100 Jarvis Park Rd, Hilton Head Island...

Pontoon Boat Rental

Island Head- Hilton Head Harbor

Book online
$225.00 - $2,200.00

description: *Explore the Low Country on your own!* ___________________________________ Rates and Duration **Two-Hour Rental:** $275 **Three-Hour Rental:** $375 **Four-Hour Rental:** $475 **Five-Hour Rental:** $549 **Six-Hour Rental:*...

Five Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 5 Days 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...

Hilton Head Sunset Cruise (2 Hours)

Hilton Head Boat Charters

Book online
$375.00 - $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: Experience the very best that the waters of the...

Four Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

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...

Romantic Sunset Cruise

Island Time Charters

Book online
$399.00

The most spectacular views and vivid colors! Duration 2 Hours About Come aboard for an enchanted, romantic cruise! Bring your favorite bottle of bubbly and we will provide the rest. This charter includes a sweet treat, fresh flowers, and...

Weekend 9:30 am-3:30 pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekend 9:30 am -3:30 pm - Golf Cart Rental *Must have valid Driver's License to rent a cart.*

Three Hour Dolphin Strand Feeding Excursion

duration: 3 Hours cancellation_summary: 24 Hours in advance group_size: 12 to 14 description: See dolphins up close! About Dolphin strand feeding is a unique activity of dolphins in the Lowcountry in which a small group of 3 to 5 male dolphins...

6 Day Rental

Island Life Rentals and Tours

Book online
$30.00 - $215.00

duration: 6 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...

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