Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Lovely villa near the water with private...

Summary:Queens Grant 759The Space:Escape from the hustle and bustle of everyday life to this peaceful villa located within a mile of the beach! Savor a outstanding location surrounded by handsome nature, great dining eateries, and countless golf...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Dog friendly home with private pool, WiF...

Summary:Crabline Court 31The Space:Find the ideal group hideaway at this family-friendly beach home, located just a half-mile from the beach. You’ll adore the palm-studded backyard, highlighted by a covered private pool. Fire up the gas grille for...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
One Bedroom Ocean View Condo!

This beachfront 1 bedroom, 2 bathroom 5th floor villa features amazing ocean vistas from every window. Upon entering, the entirely equipped kitchen is on the right, ideal for preparing meals. There is a breakfast bar for two as well as a dining...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
3rd Floor Condo with pools, tennis/pickl...

Summary:Spa On Port Royal Sound 1322The Space:Welcome to your serene hideaway in Hilton Head Island! This newly modernized condo is the ideal family-friendly getaway, located in a calming beachfront community. Located on the 3rd floor, it offers...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Family-Friendly Oasis. Beautifully Lands...

Welcome to Hilton Head Beach Villa 27!! Oceanview Villa with Pool Access and Family-Friendly Conveniences!Exciting News: Our Charming New Swimming Pool is Now Open!This villa offers a prime oceanview location and direct access to a striking...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Spacious Home 2 Masters Golf / Lagoon Vi...

Roomy 4BR/4BA home in Palmetto Dunes with a private pool/spa is a short 2 block walk to the beach. Also there is a newly added dock on the 11-mile lagoon.The home contains 2 Master Suites with king beds – one with an attached screened porch and...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 15

Hilton Head Tours & Activities

Gift Card

Wateree Marina

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

Private Food Tour

Food Tours Hilton Head

Book online
$695.00

description: Customize Your Tour! Duration 3 hours What's Included: - A private luxury SVU pickup for 6 - A knowledgeable tour guide About This tour is made especially for you. After you book the tour, our tour guide will contact you...

Nine Day Bike Rental

Wheelz of Hilton Head

Book online
$60.00 - $120.00

description: Nine Day Bike Rental Rates Duration 9 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...

One Month Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$180.99 - $361.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Luxury Pontoon Rental

Shelter Cove Marina Boat Rentals

Book online
$315.00 - $1,000.00

meeting_point: Shelter Cove Marina description: Duration 2 to 8 Hours About Rent a Luxury Pontoon, our most popular rental with all the advanced features you could want in a boat! Pontoon Boat Rental includes: ● 150 horsepower Yamaha...

Round Trip To Downtown CHS

Daniel Island Ferry

Book online
$10.00 - $50.00

duration: 30 Minutes cancellation_summary: 48 Hours before departure - refund or credit available. 24-28 hours before departure - credit for a future trip. Inside of 24 hours - no refund or credit. meeting_point: 1 river landing drive, Daniel...

Donations

Daufuskie Island Gullah Heritage Society

description: Daufuskie Island Gullah Heritage Society is a non-profit 501(c)3 organization that is working to help restore the old Gullah homes, clean up and maintain Gullah cemeteries on Daufuskie Island. Many of the Gullah homes are deteriorating...

Camellia Talk & Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $25.00

description: Camellias are fascinating plants with a rich history. While they are not native to the American continent, they have been part of the southern landscape since the 1700s. Come and learn about the history, diversity, and significance of...

Guided Paddleboard Tour

duration: 1 hour tour cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! description: H2O Sports is thrilled...

One Hour Rental (Walk Up)

South Beach Bike Rentals

Book online
$20.00 - $49.00

description: Enjoy miles and miles of scenic bike paths Duration 1 hour About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

Glow in the Dark Splatter Session

Color Me Greenville

Book online
$55.00

duration: 30 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: $55 per person for Glow in the Dark Splatter Session. description: It’s your invite to light up the night...

2 Week Rental (Walk Up)

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book...

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