Hilton Head, SC Vacations

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Featured Vacation Rentals

Ideally located condo with pool, tennis ...

Beckenham 103Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beckenham 103 is an charming condo in Port Royal Village, just a fast walk to the beach. For even...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Inviting Coastal Villa Short Walk to the...

Summary:Fiddlers Cove 15FThe Space:Located in the Fiddler's Cove Beach & Racquet Club, only 7 mins. from the Hilton Head Airport, this appealing and peaceful Hilton Head Island condo sits just a short walk to the beach and includes a wide variety of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Direct Ocean View Condo with balcony, po...

Summary:Shorewood 211The Space:Welcome to your oceanfront heaven in Hilton Head, SC! This striking condo offers beautiful direct ocean vistas and is ideally located on one of the island's best beaches. With a enormous private balcony, you can soak...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2 Bedroom in the center of the resort

Welcome to this beautiful 2 bedroom, 2 bathroom villa located in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island. This handsomely decorated getaway offers the ideal blend of comfort and style, ideal for a calming hideaway. Step...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Oceanfront Coastal One Bedroom Corner Vi...

Welcome to Oceanside Heaven, this bright and inviting oceanfront corner villa was newly refreshed throughout in 2026 with refreshed décor, and two completely updated bathrooms.Upon entering, natural light pours through a wall of windows, creating a...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 2
Charming condo near the beach with outdo...

Forest Beach Villas 409Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to handsome Hilton Head Island at this fourth-floor condo just steps from...

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

Hilton Head Tours & Activities

Stand Up Paddle Board Rental

Forest Beach Surf & Cycle

Book online
$60.00 - $200.00

description: Rent with us! Duration 1 day, 3 day, or 1 week About Forest beach surf & cycle is your source for Hilton Head Island SUP rentals

Beach Discovery Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Join a museum naturalist on an amazing nature tour!* ___________________________________ Duration 1.5 Hours ___________________________________ About Ever wonder who makes those holes in the sand—or when and why sea turtles...

Bachelor/Bachelorette

Flip Flop Charters

Book online
$895.00

description: Explore Calhoun Street! Duration 4 hours About If you’re looking for a picturesque location to raise a glass and toast the happy couple, we’d love to help you celebrate! Waterfront bars are an excellent choice. With a...

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...

One Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$39.99 - $129.99

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...

Private Fishing Charters

Performance Fishing Charters

Book online
$525.00 - $1,400.00

description: Hilton Head’s premiere fishing charter! Duration 3-8 Hour Rentals **Up to 4 people** Possibility for 5 with children About Located on Hilton Head Island, your charter will be guided by Captain John Cloyd, a USCG...

Dolphin & Nature Tour

Dolphin and Nature Tours

Book online
$5.95 - $33.95

duration: 90 minutes max_age: 99 description: Rates - Adults (Ages 12 and up) - $33.95 - Child (Ages 2-11) - $18.95 - Wee One (Children under 2) - $5.95 ___________________________________ Duration 1.5...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

description: Explore Coligny and its culinary offerings! Duration 2 hours and 30 minutes What's Included: - All tastings (amounts to a whole meal) - A fun and informative tour of the Coligny area About We will meet at our first location...

Shark Fishing Charter

Gone Fishing HHI

Book online
$400.00 - $700.00

description: Fish like a local! Duration & Rates **2 Hour Charter** - *$375* **3 Hour Charter** - *$475* **4 Hour Charter** - *$575* About The two hour trip is great for groups with young kids, beginners, or groups just looking to get out for...

SCM Lowcountry Boil Dinner Cruise

duration: 2 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head pricing: Adults: $145 Children 10yr-2yr: $99 Under 2: $20 description: Set sail for an unforgettable evening on the water with Outside Hilton Head’s Lowcountry Boil Dinner Cruise...

Tuesday Fireworks and Sunset Sport Crabbing Adventure

description: 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...

Curator's Tour

Coastal Discovery Museum Hilton Head

description: Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg 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