Hilton Head, SC Vacations

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Featured Vacation Rentals

Beautiful, Easy Ocean Access

2 BR townhouse condo. Attractively furnished, 1 1/2 baths, full kitchen, DR and deck overlooking striking, partially shaded pool. Across street from the beach with walk through access. Complex provides new gas poolside grilles for calming meals...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Beautifully Updated Home with Extraordin...

Come appreciate this wonderfully refreshed three bedroom and two bathroom home located on Palmetto Dunes' 11 Mile Lagoon system and overlooking the championship Robert Trent Jones Golf Course! The kitchen really shines in this handsome home. ...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Terrific island escape with pool, furnis...

Summary:Forest Gardens 75The Space:The island lifestyle is calling your name, so get ready for dreamy days of playing rounds of 18 on pristine courses, hitting the beach, checking out the stores and eateries in Coligny Plaza, and cycling on the...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Ocean Oriented Oasis!  Indoor Heated Poo...

Welcome to Ocean Walk 209A – Your Ideal Hilton Head Island Getaway!Discover the ideal blend of comfort, convenience, and coastal appeal at Ocean Walk 209A. Ideally located just a short walk from the sandy shores of Coligny Beach and the vibrant...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 3
Charming French Inspired Villa, Dog Frie...

Summary:Evian 140The Space:Escape to Hilton Head Island and settle into this impressive French-inspired villa, designed for effortless relaxation and coastal fun. With access to a shared outdoor pool and tennis courts, plus thoughtful amenities...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Retreat Condo with  panoramic lagoon vie...

Summary:Calibogue Club 2630The Space:Centrally located in Sea Pines Resort, this townhouse style condo has been completely refreshed and includes expansive lagoon vistas from the deck, a new kitchen island and appliances, new floor, and new linens...

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

Hilton Head Tours & Activities

Black & Blue Fishing Charters

Black & Blue Charters

Book online
$425.00 - $1,700.00

description: Black & Blue Duration & Rates **Three Hour Fishing Charter** - $625.00 *Will catch mostly sharks* **Four Hour Fishing Charter** - $750.00 *Most popular for families* **Five Hour Fishing Charter** - $900.00 *Catch your...

Friday Feeding Frenzy!

Coastal Discovery Museum Hilton Head

Book online
$15.00 - $20.00

description: Duration 1 Hour About TGIF ... even for our animals! Our reptiles, amphibians, fishes, and marine invertebrates all know that Friday means FRIDAY FEEDING FRENZY! Join our animal care staff and learn the ins and outs on how we care...

PVT Dolphin Eco 6p

description: *Our Most Popular Boat Trip!* --- Description Explore the marsh and search for the infamous Atlantic Bottlenose Dolphin... Join us for a tour on Broad Creek watching for birds and dolphins in the salt marsh ecosystem. Explore...

13 Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$102.18 - $243.23

description: Enjoy miles and miles of scenic bike paths Duration 13 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...

Nine Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$70.74 - $168.39

description: Enjoy miles and miles of scenic bike paths Duration 9 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...

Four Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$600.00

description: Duration 4 Hours ___________________________________ About *Most Popular* Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, King Mackerel, Cobia, Triple Tail, Sharks! (Species Depend On Season, Tide ...

Six Day Electric Bike Rental
Book online
$250.00

duration: 6 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...

Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: Day rental (24 Hours from the time of pick up) cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: *Perfect for your day exploring around Hilton Head!* Duration All day *All rentals must be...

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! ...

Fishing Charter

Top Shot Sport Fishing

Book online
$650.00 - $1,650.00

description: Rates - 4 hour Trip- $650 - 5 hour Trip- $750 - 6 hour Trip- $900 - 8 hour Trip- $1200 - 10 to 12 hour Trip- $Please call to book

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

description: Duration 3 Hours About Learn the secrets of Hilton Head’s history and the fascinating stories that bring it to life. This 3-hour expert guided tour takes you to five nearby historic sites in an air-conditioned bus. You will...

Day Rental

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: 1 Day description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Additional Fees - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free (1 lock per 2 bikes) About - Perfect for a day...

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