Hilton Head, SC Vacations

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Featured Vacation Rentals

Lovely townhome with balcony, tennis & W...

Ketch Court 821Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your next Hilton Head vacation playing tennis, practicing your drive, and calming on the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Charming one bedroom villa in Hilton Hea...

This beautiful one bedroom villa is sure to be your home away from home on vacation in Hilton Head! Coastal vibes run throughout this striking villa. The dining area table seats six with three additional seats at the bar. The completely equipped ...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
Golf course-view condo near beach with p...

Turnberry Village 288Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate a coastal golf hideaway at this fairway-view condo overlooking Palmetto Dunes...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Unbeatable views from private pool with ...

Wren Drive 18Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate waking up to the sights and sounds of this lush island in the Lowcountry. This home is...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
Marriott Sunset Pointe 2025 PGA Tour RBC...

*** Sanitation/Cleaning Update ***Over the next few months, when guests are in hotels within the Marriott portfolio, they will notice a number of additions to our cleaning regimen designed to set an even higher standard of cleanliness for the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stunning, family-friendly condo w/shared...

Harbourside 7150Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Have the vacation of a lifetime staying in this rare, top-level, end-unit with a wrap-around...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

One Hour Sunset/Dolphin Cruise

Lowcountry Cowboy Fishing Charters

Book online
$40.00

duration: 1 hour meeting_point: Lowcountry Cowboy Fishing Charters description: Hilton Head has a ton of dolphins, and we wont come back to the dock until you see some! The sunsets are world class too! It's the perfect way to spend an hour enjoying...

2 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$18.00 - $100.00

duration: 2 Days meeting_point: Hilton Head Island, SC description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day...

Trolling/Bottom Fishing Trip

Above and Below Charters LLC

Book online
$3,000.00

Let's Adventure! Duration 12 Hours About Gulf stream trip up to 100 miles offshore targeting Pelagic fish such as Marlin, Sailfish, Wahoo, Mahi Mahi, Tuna, with the occasional bottom fishing on the way back in. More...

Lake Wiley Boat Rental

Enjoy a fun day in the sun! Duration 8 hours About This boat is perfect for a fun day in the sun! Located at Lake Norman in Charlotte NC! Specifications - Year: 2016 - Length: 22ft - Make: Bennington ...

Baby Gear Rental • Four Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $150.00

Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 4 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

2.5 Hour Hilton Head Guided Boat Tour

Bluewater Adventure - Hilton Head

Book online
$115.00 - $149.00

Rates - Adults - $135 - Children - $115 - Fireworks Tour every Tuesday night - $135 ___________________________________ Duration 2 hours and 30 minutes ___________________________________ Guided boat tours offered daily! Adventure...

6 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$30.00 - $215.00

Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours self pick up and drop off available. Attendant will text you lock...

Valentines Nature Art for Seniors

Hilton Head Island Recreation Association

Book online
$25.00

duration: 1.5hrs meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: Maximum 20 people description: Come join Moore To Life and Island Rec Center for a holiday craft day. Give the gift of nature. Whether...

Bike Rental • Three Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $80.00

duration: 3 Days 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...

Climbing Wall Rental

Hilton Head Island Recreation Association

Book online
$100.00 - $400.00

duration: 2 Hours meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: 10 description: Are you celebrating a birthday or want to schedule a group Climb? Come to our Indoor Climbing wall for a 2-hour rental...

Inshore & Nearshore Fishing Charter

Palmetto Lagoon Charters

Book online
$495.00 - $1,245.00

24' Pathfinder - Near Shore Fishing Trips ___________________________ Description Near shore fishing on a 24 foot Pathfinder. Scope out the local near shore waterways on this amazing vessel with our very own homegrown, very salt worthy native...

Shrimping

May River Excursions

Book online
$300.00 - $400.00

*Experience sea life like never before!* ___________________________________ **Please note**: Shrimping is only available from August-December ___________________________________ Rates **Private Charter** - $300 2 hours (for 6 people and...

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