Hilton Head, SC Vacations

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Featured Vacation Rentals

Corner-condo w/ panoramic view & wraparo...

Hampton Place 6209Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get access to one of the best vistas Palmetto Dunes has to offer in this inviting condo on...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Bright & inviting condo near the beach w...

Bluff Villas 1673Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located right in the heart of South Beach, this 1,200 sq. ft. rental is just steps from the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Newly Renovated beachy condo w/shared po...

Sea Side Villas II 285Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate beach hideaway at this striking oceanfront condo in Hilton Head, SC...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Beautiful 2 BR Villa - Hilton Head Marri...

Description ????Welcome to your Charming Two-Bedroom Garden View Villa at Marriott’s Monarch in sunny Hilton Head Island, South Carolina! This inviting getaway blends serene natural surroundings with thoughtful luxury, ideal for families, couples...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Wonderful vacation condo featuring share...

Beckenham 109Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beckenham 109 is a beautiful end-unit villa in Port Royal Village with a splendid view of the 9th...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
300 steps to the beach! - Pet Friendly R...

Located in the very beautiful Forest Beach, this home features 2 Master Bed Rooms en suite and 2 additional bedrooms with a shared hall bath. Just a short walk to eateries and shopping of Coligny Circle. Freshly redecorated and furnished with a...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

Lowcountry Lake Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations rescheduled when possible; full refund if unable to reschedule meeting_point: 100 Jarvis Park Rd Hilton Head Island, SC US 29926 description: Join us at Jarvis Creek Park on...

Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $900.00

description: This trip is great for kids or anyone who wants a little taste of Lowcountry fishing! **If you don't see a time on the calendar that works for you, text us at 843-422-5438 to see if we can accommodate you!** Duration 2 to 6...

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$80.99 - $161.99

description: 10 Day Rates: - 16” Kids Beach Bike: $80.99 - 20” Kids Beach Bike $80.99 - 24” Youth Beach Bike: $80.99 - 26” Bike w/ Child Seat: $95.99 - 26” Mens Beach Bike: $80.99 - 26” Unisex Beach Bike: $80.99 - 12" Balance Bike...

The Bulldog

Bulldog Fishing Charters

Book online
$625.00 - $1,700.00

meeting_point: 1 Hudson Rd Hilton Head Island, SC 29926 description: *The Bulldog* _____________________________________ Rates **Three Hour Fishing Charter** - $625.00 *Will catch mostly sharks* **Four Hour Fishing Charter** - $750.00 *Most...

Two Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$59.99

description: The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

Private Lesson with Doug Weaver

Palmetto Dunes Golf Academy

Book online
$160.00 - $800.00

About Doug Weaver, Director of the Palmetto Dunes Golf Academy Golf Digest South Carolina Top-Ten Instructor. Doug Weaver is a former PGA Tour Pro, US Open record holder and recent Lowcountry Golf Hall of Fame member. His weekly TV show and...

Sunset Sport Crabbing Adventure

description: Join us for a Sport Crabbing Adventure with a sunset! Duration 2 hours About Our summer night Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on...

Hilton Head Dolphin Tours (2 Hours)

Hilton Head Boat Charters

Book online
$325.00 - $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: The best 2-hour charter on the island Ride in...

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...

Donuts with Santa Cruise

Vagabond Cruise

Book online
$24.95 - $44.95

duration: 60 Minutes cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 accessibility: Not Wheelchair Accessible description: **Donuts with Santa Cruise** Experience the joy of the...

2 Hour Wambaw Creek Wilderness Area Blackwater Tour
Book online
$55.00 - $110.00

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...

Community Fishing

Hilton Head Island Recreation Association

Book online
$25.00

duration: 2 Hours meeting_point: Rowing and Sailing Center group_size: Up to 20 people description: Enjoy a night of fishing and education with your family and learn some pro tips from some of the Lowcountry's most sought-after Fishing Captains! In...

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