Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Private pool - space for the whole famil...

This bright and roomy home, located on a peaceful cul-de-sac, has everything you will need to savor your next family adventure on Hilton Head!The pretty LIVING ROOM greets you as you enter through a two-story entry. With classy and comfortable...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Stunning Oceanfront Views! Newly Renovat...

Discover the ideal coastal getaway in this delightfully refreshed one-bedroom, one-bath villa. Savor seamless connectivity with wireless internet and expanded cable TV while taking in the striking oceanfront view. The private bedroom, featuring a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Updated Harbour Town Hideaway with Pool ...

Racquet Club Villas 2346Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'***The reconstruction project in the subdivision will be taking place through...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Corner unit townhome with lots of light ...

This dazzling, freshly refreshed townhome is conveniently located on the George Fazio Golf Course in Palmetto Dunes - just a short walk to the beach! This 2-bedroom end-unit villa in Palmetto Dune’s Turnberry Village has been thoughtfully...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront, Pool, Bike or Walk to Colign...

133 Dune Lane, Hilton Head Island is a 4-bedroom, 4-bath oceanfront home epitomizes casual beach living at its best. Wake up to beautiful vistas of the ocean from every room, including the kitchen, living room, dining room, and all four bedrooms...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Custom-built home near the beach with pr...

Port Au Prince 4Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located within a mile drive or bicycle cruise of the beach, this Shipyard home is...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Saint Helena Day Sail

Otter Sailing Adventures LLC

Book online
$300.00

description: Experience the awe-inspiring beauty of Low Country waterways and the Saint Helena Sound Duration 2.5 hours About Private Sailing Charter - Price Per Group (up to 6) Experience the awe-inspiring beauty of Low Country waterways...

SC Pimento Cheese Festival- Vendor
Book online
$30.00 - $125.00

duration: 8 hours meeting_point: 6071 St Andrews Rd, Columbia, SC 29212 description: With over 2,500 in attendance in our 1st SC Pimento Cheese Fest last year, we believe this year will be bigger and better! Promote your business in front of the...

Lake Keowee - Jet Ski Rental

Captain Cams Watersports

Book online
$275.00 - $350.00

duration: 4-7 Hours meeting_point: 757 Keowee Baptist Church Road Six Mile, SC 29682 min_age: 25 group_size: Up to 6 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight...

Hilton Head to Daufuskie Island

Island Head - Broad Creek

Book online
$10.00 - $30.00

duration: 45 Minute Ferry Time cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Hilton Head -> Daufuskie Island One Way...

28 Day Rental

Island Life Rentals and Tours

Book online
$96.00 - $740.00

duration: 28 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...

Echaw Creek Tour

Nature Adventures Outfitters

Book online
$52.00 - $104.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

One Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$21.99

description: Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

Mini Boat Dolphin Tour

Lowcountry Watersports

Book online
$199.00

duration: 2 hours cancellation_summary: Cancellations allowed up to 48 hours before the scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 max_age: 99 group_size: 2, 3 or 4 per mini...

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...

Skye

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

Gift Card

Drifter Excursions

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

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