Hilton Head, SC Vacations

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Featured Vacation Rentals

4 BR Private Home Close to South Beach M...

6 Beachside Drive | One Minute Walk to the Beach*4 Bedrooms | 3 Bathrooms*Sleeps 8*1 King, 1 Queen, 4 Twins*3 TVs | DVD | Alexa | Wi-Fi | Keurig*8 Beach Towels for Guest Use*Beach Gear Credits Supplied *Savor Rounds of Golf & Kids's Activities with...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Charming Townhome with Golf Course View,...

Summary:Shipmaster 901The Space:Welcome to an extraordinary beach or golf hideaway located in Shipmaster Villas within Shipyard Plantation, a private gated community next to Hilton Head Island’s Coligny Beach! This End-Unit Townhome is...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Condo with Coligny Beach views, outdoor ...

Summary:Breakers 237The Space:Feel the ocean breeze on your face from the comfort of a comfortable condo in Hilton Head Island! This beach-view condo, located in The Breakers Resort, is the ideal home base for beach lovers of all ages. Appreciate...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Stunningly remodeled villa with shared p...

Summary:Evian 154The Space:This marvelous second floor villa features new touches from top to bottom. The plank floor, furnishings, kitchen and bathrooms are all new for guests! As you walk up the staircase, you're greeted with bright, coastal...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Lovely single level Palmetto Dunes home ...

This alluring single level Palmetto Dunes home has undergone some recent updates in summer 2024! Upon entry you are immediately drawn outside to the wrap around lagoon vistas! The enormous living room has plenty of seating for the whole family with...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Comfortable Two Bedroom Villamare Condom...

Escape to this appealing two bedroom, two bathroom condominium located in the Villamare community within the acclaimed Palmetto Dunes Oceanfront Resort. This inviting getaway offers comfort and convenience with a roomy layout, ideal for families or...

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

Hilton Head Tours & Activities

PB Private Outback Excursion - 16 passenger

description: The Perfect Combination of Adventure and Fun! ___ Description This trip combines two of our most popular trips, The Dolphin Eco Tour and The Guided Kayak Tour, in an over the top remote location. A favorite of locals and visitors...

Horse Whispering (Montage Guests)

duration: 45min group_size: 4 description: Most people are taught to make horses respond to them. In this experience, you'll learn something fundamentally different: how to speak the horse's own language. Led by Longfield's Equestrian Director, a...

SCM Lowcountry Shrimping Excursion

description: ___ Description Fall in the Lowcountry is shrimp season. Come and join us for what the locals consider a true right of passage. Learn how to throw a cast net for shrimp the way local watermen have for generations. On this 3-hour...

Romance Package

Hilton Head Helicopter Tours

Book online
$100.00

pricing: $100 + Taxes/Fees description: Create unforgettable memories with your special someone aboard a private helicopter tour designed to ignite romance. Sip on complimentary champagne, savor a hand-selected box of chocolates, and let love take...

Baby Gear Rental Package • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$190.00 - $235.00

duration: 1 Day cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

July 4th Fireworks Cruise
Book online
$65.00 - $95.00

description: *Get the best seat in the house for the Independence Day fireworks!* --- > Prices >- **Adults:** $145 >- ** All Children:** $95 (12 and under) --- Description Book this cruise early, it is extremely popular! Incorporates a 2...

Four Day Bike Rental

Wheelz of Hilton Head

Book online
$43.00 - $86.00

description: Four Day Bike Rental Rates Duration 4 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...

Lunar Paddle at The Landing

Saluda Lake Landing

Book online
$8.00 - $60.00

duration: 2 hrs cancellation_summary: Cancellations made 48 hours or more before the event are eligible for a full refund. Cancellations made within 48 hours of the event are nonrefundable, but your ticket can be transferred to a future paddle...

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...

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...

Two Day Bike Rental

Wheelz of Hilton Head

Book online
$35.00 - $70.00

description: Two Day Bike Rental Rates Duration 2 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 getting...

Vanishing Island Expedition™ - Three Hour

Island Life Rentals and Tours

Book online
$65.00 - $780.00

duration: 3 Hours group_size: 12 - 14 Max description: Our Three-Hour Beach Combing Expedition to "Vanishing Island™" starts at The Old Oyster Factory docks near the top of Broad Creek. As we glide through the Lowcountry Salt Marsh, you'll watch...

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