Hilton Head, SC Vacations

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Featured Vacation Rentals

Inviting Condo with pool, tennis court a...

Summary:Treetops 7705The Space:Located in the heart of Hilton Head, this appealing condo offers a ideal getaway for your vacation hideaway. With a screened-in patio overlooking lush greenery, an on-site pool for a invigorating dip, and a tennis...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Exceptional Beach Retreat! Breathtaking ...

Welcome to Oceanside Villas 331 - Your Coastal Escape with Stunning Ocean Vistas!This attractively refreshed 1-bedroom, 1-bath unit, refreshed in 2020, offers amazing ocean vistas from both the living area and private balcony. Located just steps...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Luxury 7BR Beach House w/ Pool, Hot Tub ...

Sandy Beach Retreat is a extravagant 7 bedroom (plus a ground level room with Queen pull out couch), 6 full bathroom (plus 2 half baths) home located steps away from Burkes Beach access. Located in the charming Burkes Beach community of Hilton Head...

  • Hilton Head
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 22
3133 Villamare - Direct Oceanfront Views...

This attractively refreshed 3 bedroom, first floor corner villa offers striking ocean vistas from every room and was thoughtfully refreshed in 2026. Updates include new furnishings in the living and dining areas, updated floor throughout the main...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
NEW! 1 BD Apt~Beach Access~Clean~Great L...

Time for a relaxing beach trip! Just mins. to the beach, private 1 bedroom apt that is all new! Park outside your door! King bedroom with tons of storage & TV. Sizable bathroom with tile shower! Living Room has 50" Intelligent TV and access to a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
Charming Oceanview Retreat! Recently Rem...

Feel Coastal Luxury in This Stunning Oceanview Villa: Hilton Head Beach Villa 16!Exciting News: Our Handsome New Swimming Pool is Now Open!Spanning three levels, this oceanview villa features floor-to-ceiling glass doors on both the main and lower...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Fishing Charter - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

description: Duration 3 to 8 Hours Options About Near-Shore and Off-Shore Fishing. Ultra Stable, lots of shade, bean bags and Best of all Super Lucky! This experience is perfect for going after anything and possibly catching Bull-REDFISH...

PB Private Daufuskie Island Tour - 6 passenger

description: *Catch a glimpse into a fascinating chapter of Lowcountry history* --- Description Tucked between Hilton Head Island and Savannah, and accessible only by boat, Daufuskie Island is a real gem. This trip provides a glimpse into a...

DI - Daufuskie Island History & Artisans Excursion

duration: 2.5 Hours meeting_point: County Landing near D’Fuskies pricing: $85 per person description: Description This 2.5-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of...

Time Flys

Palmetto Lagoon Charters

Book online
$555.00 - $1,275.00

meeting_point: Shelter Cove Harbor, 17 Harbourside Ln, Hilton Head Island, SC 29928 (Dock H, Slip 3) description: We’re proud to welcome a classic back into the family — a beautifully restored 1993 Silver King 18, perfectly paired with a 2023...

???? Cook at Home Classic Lowcountry Boil

duration: 10 minutes meeting_point: 37 New Orleans Road Suite B, Hilton Head Island, SC pricing: * Base price: $59.99 for 2 people * Each additional person: $25.99 description: Our Lowcountry Boil bucket arrives packed with fresh, local ingredients...

Stella

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

PB Private Outback Excursion - 12 passenger

description: The Perfect Combination of Adventure and Fun! ___ Description This trip combines two of our most popular trips, The Dolphin Eco Tour and The Guided Kayak Tour, in an over the top remote location. A favorite of locals and visitors...

Hibachi Dinner Cruise

Island Head - Broad Creek

Book online
$19.99 - $109.99

duration: 2 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: Hibachi Dinner Cruise Experience an...

One Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$25.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** These strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

WAHHI Vanishing Island Beachcombing Cruise

meeting_point: Hilton Head Island, SC description: *Meet Hilton Head's dolphin population and visit a vanishing island. Collect shells and observe local wildlife. A Lowcountry favorite!* --- Description This three-hour boat cruise...

Seasonal Fireworks Cruise

Flip Flop Charters

Book online
$775.00

description: Watch fireworks at Shelter Cove! Duration 3 hours About From June to August we offer a weekly cruise to watch the fireworks at Shelter Cove. You’ll have a front row seat to see the magic aboard! This three hour cruise is only...

Hilton Head Airport Drop-off

Island Head Transportation

Book online
$230.00 - $350.00

duration: 1 Hour group_size: Up to 14 passengers description: End your trip with a smooth and stress-free departure using our private Hilton Head Airport drop-off service. Accommodating up to 14 guests, our comfortable transportation offers plenty...

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