Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Golf course and lagoon views!

This striking four bedroom and four bathroom home is all one level, no stairs! The kitchen is well outfitted with top-of-the-line stainless steel appliances and bespoke cabinetry. The living room features a 65” mounted flat screen TV, comfortable...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Wonderfully Updated Two Bedroom Villa Cl...

You'll be glad you chose this outstanding two bedroom villa with its newly refreshed kitchen, floor, beds, linens and furnishings! The floor has been updated throughout the entire villa. The beds in both the primary and guest bedrooms are new...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Sunny condo w/ ocean view balcony & beac...

Villamare 3322Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate island hideaway at this striking condo in Hilton Head. Ideal for bigger groups...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious Home 2 Masters Golf / Lagoon Vi...

Cavernous 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...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Newly Renovated Harbour Town Villa w/ Pr...

Ketch Court 824Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ketch Court 824 is conveniently located in the heart of Sea Pines. This freshly modernized...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
1 Shore Crest, Large Pool, Ping Pong, Be...

1 Shore Crest Lane, Hilton Head Island is a charming home constructed in 2022 and offers 5 bedrooms & 5 bathrooms, a sizable pool and a calming outdoor entertainment space. This enchanting beach home is just a fast 3-5 min. walk to the Burkes Beach...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13

Hilton Head Tours & Activities

Tuesday Fireworks and Sunset Sport Crabbing Adventure

Join us for a Seasonal Summertime Firework and Sunset Sport Crabbing Adventure Duration 2.5 hours About Our Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on...

Eight Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$62.88 - $149.68

Enjoy miles and miles of scenic bike paths Duration 8 Days 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 available ...

Solaris - Morning Sightseeing Cruise (up to 6 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book a luxurious morning charter aboard Harbour Town's Solaris now! **Our private charters accommodate up to 6 passengers, ensuring an intimate and...

Three Day Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$89.99

Rate 3 Day Rental: $89.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 3 Days

PB Private SUP Instruction
Book online
$75.00 - $325.00

*Get on the water with one of our custom kayak tours & classes* Outside Palmetto Bluff has a professional staff of Instructors ready to help you enjoy the fun, fitness and beauty of the fastest growing watersport in the world! All lessons...

Beginners Rowing

Hilton Head Island Recreation Association

Book online
$100.00

duration: 4 Weeks • 1 Day Per Week meeting_point: Rowing and Sailing Center min_age: 12 max_age: 18 group_size: Up to 12 Campers description: Learn the basics of rowing. We use 1-4 person shells (boats) and will teach participants basic sculling...

22' Hurricane Fun Deck

Hilton Head Island Boat Rentals

Book online
$325.00 - $1,525.00

About 22' Hurricane Deck Boat The Hurricane Deck Boat's "Fun Deck" Layout Up to 6 people Max Duration 2-8 Hours

Private Sunset Cruise (Up to 14 Passengers)
Book online
$549.00 - $899.00

duration: 2 or 3 Hours 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: The private sunset...

Shark Tooth Island Excursion

duration: 4 Hours meeting_point: Shelter Cove Marina (next to Ela's) pricing: $95/person + 20% gratuity description: *Hunt for Treasures of the Sea!* Enjoy a scenic boat ride from Hilton Head to Savannah, where you will step off onto islands to...

One Week Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$41.99

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 small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

Dolphins, Sharks & Shells!

Dolphin Discoveries Hilton Head

Book online
$475.00 - $1,065.00

duration: 3 to 6 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

13 Day Rental

Island Life Rentals and Tours

Book online
$51.00 - $355.00

duration: 13 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Find your perfect Hilton Head

Fishing Charter

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