Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Spacious and bright 2 Bedroom/2 Bathroom...

Located in Palmetto Dunes and new to the rental market with great weeks available - this entirely refreshed end unit in Inverness Village has a ideal view of the George Fazio Golf Course. Inverness Village amenities include an on-site community pool...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stylish Villa with Fast WiFi, Shared Poo...

Summary:Colonnade Club 179The Space:Located on the south end of Hilton Head Island and surrounded by greenery, this classy Colonnade Club villa is sure to be the source of many magnificent vacation memories for years to come! With space for a modest...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Lovely Two Bedroom Villamare Condominium...

Escape to a hideaway in this delightfully appointed two bedroom condominium in the charming Villamare community within Palmetto Dunes Oceanfront Resort. This inviting condo offers everything you need for a comfortable and memorable stay.The roomy...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Close to beach with pool, tennis, pool  ...

Summary:Forest Beach Villas 207The Space:Located in the heart of Hilton Head, SC, the Forest Beach Villas offer a prime location near the Coligny Circle on South Forest Beach Drive, just steps away from the pristine beach and a short walk from...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Large Oceanfront Home with Private Pool ...

Treat your family with this immense five bedroom home located oceanfront on Catboat Lane within Palmetto Dunes Oceanfront Resort! The gourmet chef's kitchen will be completely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Island Resort Getaway  3 Pools, Hot Tub,...

Summary:Hilton Head Resort 4222The Space:NOTICE: The hot water tub is down until further notice. Thank you for understanding.Boasting a plethora of on-site amenities, your ideal family beach vacation awaits at this choice 2BR/2BA Hilton Head Resort...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Salt Marsh Discovery

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

meeting_point: Coastal Discovery Museum, 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: *Learn from an expert why the Salt Marsh is so vital to the ecosystem!* ___________________________________ Duration 1 hour and 30 minutes...

Six Oaks Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Are you looking for the perfect Hilton Head setting...

Private Charter (Up to 14 Passengers)

Island Head - Broad Creek

Book online
$229.00 - $1,603.00

duration: 1 - 8 Hour Options 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 group_size: Up to 14 Passengers description: Enjoy a...

Three Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99 - $175.99

description: Single Kayak Full Day Rental: $149.99 ________________________________ Double Kayaks Full Day Rental: $175.99

BBQ Dinner Train

The South Carolina Railroad Museum

Book online
$45.00 - $90.00

duration: +/- 2.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held select Saturdays, April-September. Great for a casual date night. Guests enjoy a narrated 5-mile trip through the Fairfield...

Boat, Bite, and Bar at Old Daufuskie Crab Co.
Book online
$10.00 - $49.99

duration: 3 Hr 45 Min 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: Boat, Bite, and Bar at Old Daufuskie Crab...

Three Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$29.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** 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...

Brunch Under Sail

BC2 - Island Head

Book online
$19.99 - $89.00

duration: 2 Hours meeting_point: Broad Creek Marina 18 Simmons Rd. description: A Luxury Brunch Sailing Experience Step aboard our luxury catamaran for a truly elevated morning on the water. Brunch Under Sail is a two-hour sailing experience...

2.5 Hour Firework Tour

Hilton Head Island Tours

Book online
$425.00

description: *Learn about our Coastal Ecology on our 2hr Private Crabbing Excursion!* ___________________________________ Rates **Private Charter** - $425.00 *(Up to 6 passengers)* ***All ages welcome! | Maximum of 1200...

Two Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$380.00

description: Duration 2 Hours ___________________________________ About Learn about fishing, catch sharks and other species and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you...

Private Charter to Daufuskie

Daufuskie Difference

Book online
$350.00

meeting_point: Hilton Head description: Now Offering Private Boat Charters for Hilton Head Island. Get outside and enjoy a Dolphin Nature Cruise, Brunch or Lunch, or any of our other great Charter Options.

One Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$21.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** 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...

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