Hilton Head, SC Vacations

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Featured Vacation Rentals

Riveting condo home with hot tub, sauna,...

Hilton Head Resort 4226Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make this adorable condo your resting spot for your next vacation! Check out Folly...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Spacious Dog-Friendly Waterfront Getaway...

St George 11Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you are looking for a family or group hideaway in one of the most sought-after communities on...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Water-view condo with covered deck, on-s...

The Cottages 30Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A modern island escape awaits at this condo at the Cottages. Located in the resort community of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3 Bedroom/3.5 Bathroom Two-story Villa N...

HILTON HEAD ISLAND. Handsome 2, 3, and 4 bedroom two-story villas are attractively decorated and have open floor plans, vaulted ceilings, skylights, decks, and screened porches. On-site amenities include private pool, spa, bath home, and kids's...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Well Updated with Beach Contemporary Dec...

This refreshed, gorgeous two bedroom, two bath villa is located directly beside the Robert Trent Jones Driving Range and Clubhouse and is also just steps to the pool! You will feel instantly on vacation as you enter this coastal villa! The warm and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
19 Sand Dollar, Luxury 2nd Row Home, Che...

19 Sand Dollar, Hilton Head Island. Welcome to this impressive second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, savor plenty...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16

Hilton Head Tours & Activities

Full Day Fishing Trip

BackCountry Light Tackle & Fly

Book online
$895.00

Duration 8 Hours About Light Tackle and/or Fly Fishing Experience Explore more localized waters from the Departure Boat Ramp! 375 lbs maximum (all passengers): - 2 Adults - 1 Child, 1 Adult - 1 Adult

Forest Ride

Daufuskie Marsh Tacky Society

Book online
$65.00

Duration 30 minutes About Designed for the enthusiast who is short on time or has fewer miles in the saddle but wants to check riding a Marsh Tacky on Daufuskie off of their list, this experience offers pristine, maritime forest and marsh views...

Nine Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$70.99 - $141.99

9 Day Rental Rates: - 16” Kids Beach Bike: $70.99 - 20” Kids Beach Bike $70.99 - 24” Youth Beach Bike: $70.99 - 26” Bike w/ Child Seat: $85.99 - 26” Mens Beach Bike: $70.99 - 26” Unisex Beach Bike: $70.99 - 12" Balance Bike: $70.99 ...

Bike Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$40.00 - $200.00

duration: 14 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...

Private / Dolphin Strand Feeding Expedition

Dolphin Discoveries Hilton Head

Book online
$395.00 - $445.00

duration: 3 Hours cancellation_summary: We have a 48 hour cancelation policy. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - Hilton Head, SC | Meet at the end of the wooden...

7 HR Ult Day

Outside

Book online
$87.50 - $1,065.00

*Full day customized adventures are the best way to see and explore the Lowcountry!* --- Description Your Day, Your Way! Outside’s signature program! The Ultimate Lowcountry Day is just that – the ultimate way to experience the authentic...

Four Hour Private Inshore/Nearshore Charter

*Great fishing inshore to nearshore!* ___________________________________ Rates **Private Charter (All Ages | For up to 6 guests):** $750 About Our Hilton Head Island waters provide some of the best fishing in the world! Depending on the...

Sunset Mini Boat Dolphin Tour

Lowcountry Watersports

Book online
$249.00

duration: 2 hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 group_size: 2, 3, or 4 per mini...

Inshore Fishing Charter

Gone Fishing HHI

Book online
$475.00

Fish like a local! Duration 3 Hours About Targeting Red Drum, Black Drum, Seatrout, Flounder, and Sheepshead in local tidal creeks and nearby waterways with light tackle. This trip is great for all experience levels! More Info It’s never...

PB 2 Hour May River Kayak Nature & History Paddle

On this casual tour, you'll explore the local creeks with a naturalist guide. No kayak experience is necessary. Duration 2 hours Meeting Location - This activity will meet at the Paddle House which is located underneath the Canoe Club...

Four Day Bike Rental

Wheelz of Hilton Head

Book online
$43.00 - $86.00

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 getting around...

One Day Surf Board Rental

Hilton Head Outfitters - Bike Rental

Book online
$49.99

Rate 1 Day Rental: $49.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 8 Hours

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