Hilton Head Island Vacation Rentals Archives - Sunset Rentals Vacation Blog

History of Hilton Head Island

Situated only 45 minutes from historic Savannah, Hilton Head is the largest of the South Carolina islands stretching 12 miles along the Atlantic Coastline. Hilton Head Island offers the ultimate in Lowcountry island living – miles of unspoiled beaches, nature preserves and biking trails, world-class golf and tennis, upscale shopping and dining, and luxury Lowcountry coastal retreats. 

Hilton Head Island also offers visitors a glimpse into the fascinating history of South Carolina’s Lowcountry, a destination that has survived three wars, multiple hurricanes, and eras of feast, famine – and fame. In 2021, Travel+Leisure ranked Hilton Head #1 in World’s Best Islands but what lies behind the fame of America’s favorite island. Journey with us as we explore the fascinating history behind Hilton Head Island.

2000 BC to 1500 AD

Evidence of life over 4,000 years ago remains on Hilton Head Island today. The well-preserved Native American Indian Shell Ring is located in Sea Pines Preserve and is the oldest known archaeological site on Hilton Head Island, and one of only 50 shell rings known to still exist today. This iconic remnant of Hilton Head Island’s history measures 150 feet in diameter and is one of the most pristine examples of a shell ring remaining in the USA. 

Later, in 1335 A.D, the Native American tribes built a fortified village covering two acres along the banks of Skull Creek. This shell ring is also open to the public on a short and easy trail at the Green’s Shell Enclosure Heritage Preserve. Both these historic shell rings are today listed in the National Register of Historic Places.


Historical records show the first Spanish explorers making contact with local Native Americans in 1521, nearly two hundred years later. In 1566, the Spanish explorers built Santa Elena, a permanent settlement and Fort across the Port Royal Sound on Parris Island. They abandoned Santa Elena in 1587 to colonize further south in St Augustine, Florida. By 1663, the island was largely uninhabited except for a small population of Native Americans living off the land. 

In August 1663, English Captain William Hilton set sail from Barbados to explore land granted to the Lords Proprietors, eight Englishmen to whom King Charles II had granted power of Carolina. His original landing site was the Port Royal Sound and, on gaining first sight of the headlands, he claimed the land for Britain. 

In the spring of 1670, Captain Robert Sandford together with over 150 colonists, servants and slaves sailed into what is today Charleston Harbor claiming the land and naming it Charles Town, in honor of King Charles II. By 1672, the expanding settlement had relocated on a peninsula between the Cooper and Ashley River and …. the rest is history! Today, Charleston ranks as the #1 City in the USA

On 16 August 1698, the Lords Proprietors granted John Bayley of Ireland a barony which included most of Hilton Head Island, excluding Port Royal Sound and Skull Creek. John Bayley never once visited Hilton Head Island, instead appointed Alexander Trench as an agent to sell the property. The bulk of the barony remained in the Bayley family until after the Revolutionary War.


In 1717, Colonel John Barnwell was granted 1,000 acres of land on the NW corner of the island (now Hilton Head Plantation) and became the first white settler on Hilton Head. There was still hostility between the Spanish and British and, in 1733, the City of Savannah was founded as a barrier between Spanish Florida and British Carolina. 

By the 1750s, most of the plantations on the island were successfully growing indigo, which was being sold to the English – until the Revolutionary War. During the Revolutionary War (1775 to 1783), the British successfully took the city of Savannah (after failing to take Charleston!) and frequently raided the island, burning plantations and capturing slaves. Aside from rice, indigo was South Carolina’s most second valuable export, however trading with England had now ceased. 

It wasn’t until 1790 when William Elliott planted the first crop of Sea Island long-staple cotton that the island once again began to gain recognition. William Elliott teamed up with neighbor Will Seabrook to pioneer a new fertilizer for the cotton crops and the Lowcountry sea islands began to boom. 

The War of 1812 brought more devastation by British forces to the island, but the economy quickly resumed and, by 1860, the cotton industry on the island was lucrative with nearly two dozen working plantations.

1860 to 1940: SLAVERY & THE CIVIL WAR

South Carolina was the first US state to withdraw from the Union in December 1860, and, in April 1861, the Civil War began. After the Battle of Port Royal Sound in November 1861, more than 12,000 soldiers captured Fort Walker and Hilton Head Island fell into the hands of the Federal troops. Hilton Head Island became the headquarters for the blockade of the South Atlantic coast with an estimated forty thousand soldiers, prisoners of war, and former slaves settling on the island. The prospering rice, indigo and cotton plantations were abandoned, yet this victory meant freedom for the African Americans that remained. 

In 1862, Union General Ormsby Mitchel built the town of Mitchelville, the first self-governing town of formerly enslaved African Americans with nearly 1,500 Gullah residents. Land was confiscated, northern missionaries opened one room schools, and homes were built for the former slaves, known locally as “contrabands of war”. 

In 1864, as the troops began to move out of the area, Fort Howell was built to protect the town of Mitchelville. In 1865, the 13th Amendment to abolish slavery was signed and the Gullah community of Mitchelville were legally freed. Many moved on, others stayed on the island farming in the summer, oyster harvesting in the winter, and remaining true to the rich legacy of the Gullah culture. 

Hilton Head Island returned to nature and from the 1900s to 1950s was primarily used as a destination for wealthy private hunting groups. Today, visitors to Hilton Head can walk the quiet trails leading through historic Mitchelville Freedom Park with the original site of Battle of Port Royal, historical remnants of the town and Fort Howell, and access to an off the beaten path beach overlooking the passage taken by Captain William Hilton in 1663. 

The Baynard Plantation, built by Revolutionary War hero Captain Jack Stoney in 1793, was used as the HQ for the Union troops and was later burned to the ground. Visitors to the island today can still tour the ruins of the grand antebellum home and slave quarters on a short hike through Sea Pines Preserve.


By early 1950, Georgia timberman Fred Hack had discovered the acres of loblolly pine and live oak trees on Hilton Head and, along with JB Fraser and other investors, set up the Hilton Head Company and began to buy up acres of land to harvest lumber. Lumber mills were built and, after harvesting millions of feet of lumber, Hilton Head Company began selling off lots along the beach for vacation cottages.

The modern age of Hilton Head Island began with Charles Fraser, son of J. B Fraser. Charles had a vision to preserve the plantation history and natural beauty of the island and build an eco-friendly, resort community on his family land dominating the southern tip of the island. The first car ferry arrived in 1953, a grocery store opened at Coligny Circle in Forest Beach, and the James F. Byrnes swinging bridge was built in 1956, finally connecting Hilton Head Island to the mainland. 

Fraser’s vision for a world-class resort became a reality and a model for future resort communities across the US. Sea Pines Plantation was a stunning natural oasis with classic Lowcountry architecture and beach homes, untouched forest preserves, 5-miles of sandy beaches, championship golf courses, and the signature candy-cane Harbour Town Lighthouse. Shipyard was the second plantation to be developed on Hilton Head, followed by Port Royal and Palmetto Dunes


Harbour Town Lighthouse

Hilton Head Island is home to two lighthouses: The historic Leamington Lighthouse built by Union Troops in 1879 which overlooks the Arthur Hills Golf Course in Palmetto Dunes and the iconic Harbour Town Lighthouse in Sea Pines Plantation, built by Charles Fraser as a fun and memorable landmark and museum dedicated to the history of Hilton Head Island. The 90-ft lighthouse features ten levels of fascinating photos and artifacts, a Coast Guard Exhibit, a one-of-a-kind gift shop and views all the way to Tybee Island!

Coastal Discovery Museum

The Coastal Discovery Museum is situated on the historic Honey Horn plantation, dating back to before the Civil War. The museum is home to nine historical buildings, the Santa Elena Center highlighting the history of 16th century Hilton Head, and 68 acres of beautiful grounds with nature trails, butterfly gardens, and an ancient 500-year old Southern Red Cedar. The Coastal Discovery Museum offers guided history tours of Hilton Head Island, the Forts of Port Royal and the habitats and history of Pinckney Island.

Venture beyond Hilton Head Island to learn more about the history of the Gullah culture on a boat tour of Daufuskie Island or take a cruise of Savannah’s historic port and riverfront.

Local Tip: For traditional Gullah-Geechee cuisine, soulful blues, and warm southern hospitality, stop by Ruby Lee’s situated just across William Hilton Parkway!

Port Royal Golf Club

Tee off for a round of golf at the Robber’s Row Course set atop former civil war grounds with interpretive markers on several holes describing the historic events that took place at Port Royal.

Gullah Heritage Tours

Travel through the communities of Hilton Head Island on a two-hour narrated bus tour with native Gullah residents. The tour is fun, interactive and covers the top historic Gullah attractions on the island including the Gullah Museum, a tiny museum dedicated to preserving the Gullah-Geechee heritage and culture. 

Locally serving Hilton Head since 1993, Sunset Rentals are one of the most experienced vacation rental companies on Hilton Head Island. Our portfolio of 220+ vacation homes and villas are situated in the top resort areas of Hilton Head Island with luxury vacation amenities and a 24/7 guest concierge from our local team. 

Take a tour of the resort areas of Hilton Head Island, browse our collection of luxury rentals (many including bike & beach gear credit valued up to $350!), and book your vacation with confidence and ease with Sunset Rentals.

6 Best Farmers Markets Near Hilton Head Island

Support local businesses here in the Lowcountry by visiting a Farmers Market to stock up on fresh groceries and new products. Whether you’re looking to pick up some dinner items for a home cooked meal in your vacation rental or wanting to bring home some knowledge and practice, a Farmers Market is the perfect place to visit on your next vacation to Hilton Head Island!

1. Hilton Head Farmers Market

The Hilton Head Farmers Market is held every Tuesday from 9:00 AM to 1:00 PM at the Coastal Discovery Museum’s Honey Horn campus. Stop by to purchase local produce, seafood, meats and more while you enjoy unique vendors, food trucks, and live entertainment.

2. The Farmers & Makers Market

Every Tuesday starting March 15th through November 22nd, from 10:00 AM to 2:00 PM at The Shops at Sea Pines Center. You can find seasonal fruits and vegetables, freshly caught seafood, baked goods, barbecue, and artisan crafts!

3. Bluffton Farmers Market

Open every Thursday from 12:00 PM to 4:00 PM. Hours and days vary, please check the Bluffton website for updated details. Enjoy fresh produce, prepared foods, plants, family-friendly activities, and live entertainment.

4. Lowcountry Made Popup Artisan Markets

The Made Market takes place every first and third Sunday starting in March through December, from 9:00 AM to 1:00 PM. The Night Bazaar takes place every first Thursday from March through July and October through December, from 5:00 PM to 8:00 PM. These popup markets feature local artisans, small businesses, live entertainment, food, and drinks.

5. The Root and Bloom Market

A year round market every Saturday from 9:00 AM to 12:00 PM. Enjoy local organic produce and learn about the impact your health can have on your physical and emotional wellbeing.

6. Port Royal Farmers Market

Every Saturday year round from 9:00 AM to 12:00 PM rain or shine. Experience fresh local produce, meats, seafood, prepared food vendors, plants, and more.

Whichever Farmers Market you find yourself at, home is just a short drive away when you stay with Sunset Rentals. With a portfolio of 220+ Hilton Head Island rentals and first class service from our on-island team, you can book your Hilton Head Island vacation home with confidence and ease at Sunset Rentals

10 Best Kept Secrets on Hilton Head Island

Hilton Head Island is widely-known as one of America’s favorite islands, being voted the “#1 Island in the Continental US” numerous times by Travel+Leisure. The Island is home to 24 championship golf courses, world-class tennis facilities, action packed adventures, award-winning restaurants, and beautiful beaches, but you’ll also find that Hilton Head Island  also has some pretty special secrets that you won’t want to leave uncovered!

Here are the top 10 best kept secrets on Hilton Head Island, including uncrowded beaches, nature preserves, historical trails, wildlife viewing spots, and more! For more hidden gems to uncover on your next vacation, visit our Resort Area Tour to view beaches, activities, restaurants, shopping centers, and more across the island.

1. Daufuskie Island

Daufuskie Island is the southernmost inhabited sea island in South Carolina, located just 11 miles from Hilton Head Island. Daufuskie is only accessible by boat, so make your way over to the Daufuskie Island Ferry at Buckingham Landing to start your adventure!

Daufuskie Island is full of sandy beaches to explore, nature preserves to admire, historical landmarks to learn about, and adventures to embark on. Whether you prefer to spend the day horseback riding on the beach, biking along the ancient oak lined trails, kayaking down the waterways, small town shopping, or scouring delicious Lowcountry cuisine, Daufuskie is full of adventure for everyone.

2. Harbour Town Lighthouse Museum

The Harbour Town Lighthouse is an infamous landmark that has come to symbolize Hilton Head Island over the past five decades. Many people travel over to Harbour Town to take their annual family vacation photos with the bright red and white stripes behind them and capture stunning sunset views of the Lighthouse over the harbor, but few venture into the Lighthouse.

The Harbour Town Lighthouse Museum offers the opportunity to climb all the way to the top of the lighthouse and see Hilton Head from a whole new viewpoint. As you make your way up the long winding stairs, you’ll be able to explore the Island’s rich history and get the inside scoop on how the Lighthouse was built! Don’t miss the opportunity to see Hilton Head Island from above at one of the Island’s most famous landmarks.

3. Gullah Heritage Trail

The Gullah Heritage Trail is a historical landmark, celebrating the authentic culture of the sea islands.  Gullah is a system of traditions, customs, beliefs, art forms and West African family life that have survived slavery and are now celebrated in the free lifestyle. 

As a whole, this trail area is known as the Gullah Geechee Corridor. The brilliant tour guides on Hilton Head Island were born and raised here before the bridge connection to the mainland. They now work as guides to share their expertise with tourists who want to engage in this unique cultural experience.

4. Audubon Newhall Preserve

The Audubon Newhall Preserve is a 55 acre nature preserve striving to preserve our serene natural environment here on Hilton Head Island. They are the leading voice in conservatism here in the Lowcountry, protecting our wildlife and ecosystems.

Their foremost goal is to protect our coastal marshes, beaches, maritime forests, and wildlife, while spreading awareness to locals and visitors alike. Explore the series of intertwined trails and experience the conservation of our beloved wildlife and nature for yourself!

5. Honey Horn

Coastal Discovery Museum offers a multitude of exhibits, events, tours, and experiences, but in our opinion– Honey Horn is their best kept secret! Honey Horn is a popular destination amongst locals for photoshoots and memorable events for good reason.

You can stop to smell the Camellias, explore the century-old buildings, learn about the grounds’ historied past, cross boardwalks to Jarvis Creek marsh, and observe Marsh Tacky horses grazing through the open pasture. Discover Honey Horn at your own pace!

6. Fish Haul Beach

Fish Haul Beach Park is one of Hilton Head’s many hidden gems, offering a less popular beachfront perfect for those looking to explore and enjoy their quiet getaway. This beach access is tucked away in Bay Gall, one of the historic Gullah neighborhoods.

This beach overlooks Port Royal Sound, offering visitors the perfect space for leisurely walking, active bird watching and relaxing in the sand with beautiful beach views away from the hustle and bustle.

7. The Farmers & Makers Market

The Farmers and Makers Market is located in the Shops at Sea Pines Center, offering visitors a chance to take home a little piece of the island! Whether you prefer shopping for local produce to bring back, souvenirs to remember your trip, or unique gifts for loved ones, you won’t want to miss The Farmers & Makers Market!

The Farmers & Makers Market updates their Facebook page often with recent updates and current vendors! Find out more about books, produce, fresh foods, handcrafted art, and more. You can even visit Lowcountry Produce to order from the cafe!

8. Lawton Stables

Lawton Stables is located in Sea Pines Preserve– with trail rides, riding lessons, pony rides for children, and an animal farm available to explore. Across the 600 acres of secluded forest, Lawton Stables offers an unforgettable experience for all families.

Gallop beneath the mossy oaks, learn about the historical tales from your tour guide, and visit several farm animals including goats, miniature donkeys, miniature cows, pigs, alpacas, ponies, and chickens.

9. Skull Creek Marina

Skull Creek Marina is home to several amenities in the midst of the island’s top activities and attractions. As sailors and anglers reel into the harbor, you can sit back and watch the sunset across the water, pick up a fishing rod and catch a few, board a charter, and more!

Skull Creek is well known for its hospitality and docks, but few know that it is one of the best spots on the island to catch a beautiful sunset, fish over the sparkling water, and explore amenities.

10. Sunset Rentals

Sunset Rentals is the leading vacation rental company on Hilton Head Island, offering luxury rentals with first class service. Whether you prefer a golf course villa, oceanfront condo, or luxurious private home, we have the perfect rentals to suit your unique needs.

What makes Sunset Rentals a best-kept secret? We offer complimentary beach gear credit valued up to $350 at participating properties, express check-in with keyless entry so that you can start your vacation immediately upon arrival, and luxury rentals that you won’t find anywhere else!

8 Best Kayak & SUP Tours on Hilton Head Island 

There are endless ways to enjoy the local waters of Hilton Head Island, but a guided kayak or SUP tour with a local naturalist is by far the most intimate Lowcountry experience available. 

Hilton Head’s network of nature trails extends to miles of tranquil paddling trails that lure you away from the white sandy beaches to explore the tidal creeks, salt marshes, and coastal wetlands of Hilton Head Island. Imagine yourself surrounded by Lowcountry beauty with the freedom of paddling alongside playful dolphins and manatees, sighting minks and otters in the marshlands, and bald eagles nesting above – that’s a Hilton Head Island paddle tour! You can even paddle with your pooch

Sure you can venture out by kayak alone, but the benefits of a locally guided tour are abundant! Our local tours are tailored to beginners so if you’re a first-timer, instruction is included. Your naturalist guide is familiar with Hilton Head’s waterways (hello secret spots!), the history and habitats of our unique coastal ecosystems, and the wildlife that calls Hilton Head home. 

Begin your Lowcountry paddle adventures with our Sunset Rental’s Guide to Kayak & SUP Tours on Hilton Head Island, SC. 

1. Outside Hilton Head

Shelter Cove Harbour & Marina
Guided Tours on Broad Creek & Daufuskie Island

Explore the hidden channels of Broad Creek with the outdoor experts at Outside Hilton Head, a local favorite since 1979! Winding 7 miles inland from Calibogue Sound, Broad Creek is Hilton Head’s largest creek with calm sheltered waters, tranquil marsh channels to explore, and bountiful wildlife, birdlife, and bottlenose dolphin encounters. Broad Creek is a favorite feeding ground for our Atlantic bottlenose dolphins, playful and curious enough to cruise alongside your kayak! 

The kayak and SUP tour options at Outside Hilton Head are endless! Choose from a Guided Kayak Nature Tour, Outback Kayak Tour, Full Moon Kayak Tour, Shelter Cove Fireworks Paddle, Kayak Fishing, May River Excursions, Intro to Stand Up Paddling, SUP Yoga, or a peaceful SUP Nature Walk on Broad Creek. Group tours or private customized adventures are available and you’re your adventures are over, there’s shopping, restaurants, and amazing outdoor events at Shelter Cove

2. Kayak Hilton Head

Broad Creek Marina
Guided Tours on Broad Creek & Pinckney Island

Located across the creek at Broad Creek Marina, Kayak Hilton Head has been guiding the scenic waterways on Hilton Head since 1995. Broad Creek Marina is Hilton Head’s newest marina and offers a wide variety of dolphin and nature cruises, sailboat charters, parasailing, fishing charters, and kayak and SUP tours with Kayak Hilton Head. End your paddle experience sipping cocktails, savoring Lowcountry cuisine, and unwinding with scenic waterfront views at Fishcamp on Broad Creek or Up the Creek Pub & Grill.   

Kayak Hilton Head offers daily 2-hour guided kayak and SUP tours of Broad Creek, private full-day tours, Shelter Cove Fireworks paddle tours in the summer, and kayaking eco-tours of historic Pinckney Island, one of the best birdwatching spots on Hilton Head Island. Their experienced outdoor adventure guides are fun and friendly with an intimate knowledge of the island’s wildlife and waterways.    

3. H20 Sports

Harbour Town Marina
Guided Tours on Calibogue Sound

H20 Sports are the only water sports activity provider at Sea Pines Harbour Town with activities for every age and adventure level! Whether you’re seeking a thrill, a casual cruise, or a self-guided tour of Calibogue Sound, you’ll find it at H20 Sports at Harbour Town. Kayak and SUP tours from Harbour Town explore the Calibogue Sound, a wild ocean channel between Hilton Head and Daufuskie Island with hidden creeks, coves, and marshes teeming with life. 

H20 Sports is all about “the FUN, the WATER, and YOU!”. Tour options include guided kayak tours, sunset kayak tours, SUP lessons and tours, or customized family adventures on the water. Other water sports activities available include Hilton Head Parasailing, Alligator & Wildlife Tours at Sea Pines Forest Preserve, Dolphin Tours, Hilton Head Sailing Charters, and jet ski, wave runner, and boat rentals to head out on your own expedition. 

4. Island Water Sports

Sea Pines South Beach Marina
Guided Tours on Calibogue Sound

If you’re spending your vacation in Sea Pines South Beach, Island Water Sports at South Beach Marina is your go-to for Kayak and SUP tours of Calibogue Sound. Situated on Braddock Cove at the southernmost tip of Hilton Head Island, South Beach Marina is a scenic launching point for paddle adventures on Calibogue Sound, and one of the most spectacular sunset spots on Hilton Head Island – best enjoyed from the world-famous Salty Dog Café!    

Island Water Sports offer a 90-minute Guided Kayak Tour, or “nature walk on water” through the creeks of Calibogue Sound, stand up paddleboarding through the salt marshes of South Beach Marina, and a variety of water activities. Take a banana boat ride on Calibogue Sound, explore Vanishing Island on an eco-tour, or rent a pontoon or powerboat to plan your own adventures. 

5. Hilton Head Outfitters

Palmetto Dunes Oceanfront Resort
Guided Tours on the Palmetto Dunes Lagoon System

The Palmetto Dunes 11-mile lagoon system offers easy paddling for families and beginners. The saltwater lagoon system winds through the neighborhoods and golf courses in the Palmetto Dunes Resort area with calm waters, and an incredible variety of saltwater species for kayak fishing! The Palmetto Dunes lagoons boast some of the best island fishing on Hilton Head with an abundance of redfish, flounder, spotted sea trout, and tarpon. A South Carolina saltwater fishing license is required to fish in the lagoon system. 

Hilton Head Outfitters is located on the shores of the Palmetto Dunes lagoon system and offer single and tandem kayak rentals, three person canoes to explore and fish the calm waters of the lagoon, and inshore skiff charters with a naturalist guide. 

6. Coastal Discovery Museum

Honey Horn Plantation
Guided Tours of Jarvis Creek & Daufuskie Island

The ultimate Lowcountry experience awaits at the Coastal Discovery Museum at Honey Horn Plantation. Aside from the spectacular plantation grounds with native gardens, wildlife habitats, and excellent exhibits, the Coastal Discovery Museum offers a long list of guided eco-tours on land and water. From artisan & history tours, heritage garden tours, and wildlife tours to epic excursions on the coastal creeks, Coastal Discovery Museum has tours for every traveler. 

Take a kayak tour of Jarvis Creek, a small creek perfect for beginners and families, or immerse yourself in the full splendor of Hilton Head Island on their Kayak the Outback Tour, a 4.5-hour paddle through the peaceful and pristine creeks of Page Island and Daufuskie Island. 

7. Sea Monkeys Watersports

Hilton Head Harbor & Marina
Guided Tours on Skull Creek & Pinckney Island

Situated on the north end of the island, Skull Creek separates Hilton Head from Pinckney Island to join the Port Royal Sound. While Skull Creek is well known for its excellent waterfront dining and fresh seafood straight from the docks, it also offers some of the best paddling on Hilton Head Island with coastal charm, wildlife, and scenic views of Pinckney Island Wildlife Refuge.   

Sea Monkeys Watersports launch their guided jet ski, kayak, and paddleboard trips on Skull Creek and Pinckney Island from Hilton Head Harbor & Marina. They also offer boat rentals by the hour, perfect for a casual dolphin watching cruise with the family. Linger a little longer and enjoy fantastic food and the island’s best sunset and waterfront views at Sunset Grille, consistently recognized as one of Hilton Head Island’s best kept secrets! 

8. Vayk Gear Kayak & Paddleboard Rentals

THE source for Beach Gear Rentals on your Hilton Head, SC vacation!

There’s no need to pack a kayak or SUP when you spend your Hilton Head vacation with Sunset Rentals. Our exclusive Beach & Bike Gear credit program with Vayk Gear gives guests staying in participating properties up to $350 credit on complimentary kayak and SUP rentals to explore the Hilton Head Island rivers, creeks, and lagoons at your own pace. Vayk Gear credit can also be used towards bike rentals, outdoor games, coolers, beach chairs, umbrella rentals, and beach carts to transport it all in one trip.


1. Book your vacation to Hilton Head Island! Complimentary Beach Gear is offered year round on select Sunset Rentals vacation homes and villas with 4-21 night stays. The value of your complimentary beach gear varies by property and ranges in value from $150 – $350. 

2. After booking, watch for an email from our gear partner Vayk Gear. Your rental house name and check-in date in the subject line. Click on the link in the email directing you to the beach gear rental page and input your reservation number. The complimentary beach gear credit will be applied automatically.

3. Select your desired beach gear, add any optional extras, and check out! Choose from top quality beach gear items like bikes, chairs & umbrellas, kayaks, paddle boards, corn hole, beach carts, skim and boogie boards and more.

4. Vayk Gear will take care of the rest! Select the items you want at least 48 hours prior to your scheduled arrival date and we’ll deliver everything for you on the day you are scheduled to arrive and pick everything up on your scheduled departure day. Just leave your gear clean and where you found it the night before your scheduled departure (gear pickups start at 6am ET), we’ll take care of the rest.

All that’s left to do is take a tour of the resort areas of Hilton Head to choose a neighborhood, find a vacation home or villa with Vayk Gear credit, and start planning your HHI paddle adventures with our team at Sunset Rentals. We hope to see you on the waterways soon!

Hilton Head Island Grocery Stores & Food Delivery Services

For many travelers, shopping for groceries is a fun beginning to a vacation, but for others, well it’s a burden they would rather leave behind. One of our guests’ most frequently asked questions about Hilton Head Island is where to stock up on groceries, find the freshest seafood, and fill the cooler with beverages during their stay.   

When it comes to grocery shopping, Hilton Head Island has everything from convenient big-box supermarket chains and boutique grocery stores to roadside seafood stands, Lowcountry delis, and classic old-fashioned convenience stores. We’ve put together the Ultimate Grocery Shopping Guide to Hilton Head to help you plan your vacation to America’s Favorite Island. 


Barnacle Bill’s Fresh Seafood Market

614 William Hilton Parkway | Phone: (843) 785-9007

Barnacle Bill’s is a laid-back roadside seafood market conveniently located mid-island near Chaplin Community Park. They offer an amazing selection of fresh fish and seafood, or pick up a portion of ready-made Lowcountry boil for a feast at home.

Open daily 10AM to 5PM, closing at 2PM on Sunday.

Benny Hudson Seafood

175 Squire Pope Road | Phone: (843) 682-3474

Situated on the banks of Skull Creek, Benny Hudson Seafood has been supplying islanders with seafood straight from the dock for over 5 generations. Known as a sulfite-free facility, they offer the freshest, high-quality seafood from our local waters and beyond.

The Marketplace is open Monday to Saturday 10AM to 5PM.

Fresh Market

890 William Hilton Pkwy | Phone: (843) 842-8332

Fresh Market is an upscale grocery store just south of Shelter Cove and the entrance to Palmetto Dunes. They stock a selection of local Lowcountry organic produce, fresh baked goods, beer and wine, toiletries, and ready-made family meals to go.

Shop in-store or online for curbside pickup. Open daily 8AM to 9PM.

Harris Teeter

Main Street Village | Phone: (843) 689-6255
Park Plaza Shopping Center | Phone: (843) 785-6185

Harris Teeter is a larger supermarket chain with two locations on the island – Main Street Village near Port Royal and Park Plaza near Sea Pines Resort.

Both stores are open daily from 6AM to 11PM with online ordering, express curbside pick-up, and local delivery.

Harbour Town General Store

Sea Pines Harbour Town | Phone: (843) 363-9802

If you’re staying in Sea Pines Resort area, you can stock up on vacation essentials, groceries, and beach gear at the Harbour Town General Store. The store is situated next to the Gregg Russell Playground and is open daily from 9AM to 9PM.

Hilton Head Oils and Balsamics

Village at Wexford | Phone: (843) 681-2722

Hilton Head Oils and Balsamics sells premium olive oils, balsamic vinegars, gourmet sauces, and health and beauty products from the finest olives in Italy.

The store is open Monday to Saturday 10AM to 6PM for shopping and tastings, or to purchase online for delivery.


Shelter Cove Towne Center | Phone: (843) 842-0540

There is a large Kroger Grocery Store located in Shelter Cove Towne Center with a pharmacy, and a Kro-Bar to sip and shop! Kroger is open daily from 6AM to 11PM with convenient curbside pickup and Instacart delivery.

Lowcountry Produce Market & Café

The Shops at Sea Pines Center | Phone: (843) 686-3003

Situated in The Shops at Sea Pines Center, Lowcountry Produce serves breakfast and lunch daily and has a small specialty marketplace. Lowcountry Produce has attracted national attention for its selection of handmade pies, pickles, chutneys, relishes, sweet jellies and preserves, and southern-style chow chows.

Open daily 8AM to 2:30PM.

Palmetto Dunes General Store

1 Trent Jones Lane, Palmetto Dunes | Phone: (843) 842-2507

Located in the heart of Palmetto Dunes, the General Store is within walking distance to the beach and sells a variety of groceries, beer and wine, grab-and-go items, beach gear, candy, and ice cream. They are known for their world-famous cinnamon rolls and the best fried chicken in Hilton Head!

Open daily 5AM to 11PM.

Piggly Wiggly

Coligny Plaza | Phone: (843) 785-3881

Family-owned since 1969, Piggly Wiggly at Coligny Plaza is a one-stop shop for all your grocery needs and vacation essentials. They offer a wide variety of local South Carolina products, a “Fish n’ Tales Seafood Market” with seafood straight from the local waters, and cool Dig the Pig merchandise to take home.

Open daily 7:30AM to 7:30PM.

Publix Super Market

Island Crossing Shopping Center | Phone: (843) 842-2632
Festival Center at Indigo Park | Phone: (843) 689-9977

There are two Publix Supermarket locations in Hilton Head – Island Crossing near Sea Pines open 7AM to 10PM daily and the Festival Center near Port Royal open daily 7AM to 9PM. Publix offers online ordering for curbside pick-up and Instacart delivery on the island.

South Beach General Store

South Beach Marina | Phone: (843) 671-6784

Staying in Sea Pines South Beach? The South Beach General Store is an old-fashioned convenience store with a wide range of essentials, beach gear, beer and wine, and quality Hilton Head souvenirs.

Open daily 8AM to 7PM.

South End Seafood Market

18 Executive Park Road | Phone: (843) 540-1109

Tucked away off Pope Avenue near Coligny Plaza, South End Seafood is a hidden gem with a great selection of fresh fish and seafood native to the South Carolina Lowcountry, and a range of condiments to spice it up.

Open daily 10AM to 5PM.  

Whole Foods Market

Shelter Cove Towne Center | Phone: (843) 842-0700

For natural and organic grocery items, ready meals, and catering, Whole Foods is located next to Kroger in the Plaza at Shelter Cove Towne Center. Whole Foods Market is open daily 8AM to 9PM with online ordering options for curbside pickup and grocery delivery.


Reilley’s Wine & Spirits

Main Street Village | Phone: (843) 681-5778
Village at Wexford | Phone: (843) 785-3339

Reilley’s Wine & Spirits is the largest liquor store on Hilton Head Island with a vast selection of domestic and imported wines, champagnes, single malt liquors, small batch bourbons, flavored spirits, vintage ports, and more! With a south end and north end location, it’s easy to shop at Reilley’s wherever you stay on Hilton Head.

Open Monday to Saturday 9AM to 7PM.

Roller’s Wine & Spirits

Sea Pines Circle | Phone: (843) 842-1200
Coligny Plaza | Phone: (843) 785-3614
Port Royal Plaza | Phone: (843) 681 8454

Since 1960, Roller’s Wine & Spirits has been serving Hilton Head with specialty wines, top-shelf spirits, and quality cigars with a team of sommeliers on staff to help you shop. They also offer free tastings in-store, online shopping and delivery (excluding liquor), and a wide selection of domestic and imported cheeses, cured meats, and specialty food products to order.

Open Monday to Saturday 9AM to 7PM. 

Sea Pines Liquor

The Shops at Sea Pines Center | Phone: (828) 808-3426

For Sea Pines Resort area vacationers, this is the only liquor store inside the gates to stock up on spirits! Sea Pines Liquor stocks a wide selection of award-winning wines, top-selling spirits, and more than 35 varieties of moonshine. Be sure to snap a selfie with Dan the Moonshine Man!

Open Monday to Saturday 9AM to 7PM.


Low Country Grocery Runner

Phone: (843) 505-8568

For the past 17 years, Low Country Grocery Runner has been providing concierge-level grocery deliveries to locals and visitors on Hilton Head Island. Their motto is “shop on-line not in-line” and you’re guaranteed a stress-free shopping experience with delivery directly to your Hilton Head Island vacation rental. They also offer a choice of private chef experiences from family-style Mexican Nights and Lowcountry boils to formal fine dining and wine pairings at home.


Hilton Head Farmers Market

Coastal Discovery Museum | Tuesdays 9AM to 1PM

The Hilton Head Farmers Market at Honey Horn Plantation features the freshest produce from local farmers and growers. You’ll find everything from free-range meats, fresh seafood, and quality fruit and veg to handmade sweets and pastries, and all the ingredients for the perfect charcuterie board. Be sure to sample the food trucks, explore the grounds and exhibits at the Coastal Discovery Museum, or book an afternoon tour of the island with a local guide.

Farmers & Makers Market

The Shops at Sea Pines Center | Tuesdays 10AM to 2PM

If you’re staying in the Sea Pines Resort area, the weekly Farmers & Makers Market is the perfect stop for local grocery shopping. The market hosts a diverse group of vendors, artists, and local farmers with fresh farm-to-table fruit and vegetables, seafood straight from the boats, southern-style BBQ, and one-of-a-kind artisan products for gifts or souvenirs to take home.

Wednesdays at Wexford Outdoor Market

Village at Wexford | Wednesdays 10AM to 2PM

Every Wednesday (May through September) the Village at Wexford hosts a sprawling open-air farmers’ market with dozens of local vendors. Stock up on meats and fresh produce, home-baked goods, and Lowcountry delicacies, and take advantage of your Market Card with great specials at participating Village at Wexford retailers and restaurants.

Hilton Head Community Market

Shelter Cove Community Park | Saturday 9:30AM to 12:30PM

The Hilton Head Community Market at Shelter Cove is the best place to be on a Saturday morning! The market features some of the best local farmers, bakers, and artisans in the Lowcountry with everything from smokin’ good BBQ and seafood to preserves, honeys, and sweet treats for the kids, As a true community market, your shopping supports local businesses and gives back to a wide range of featured Hilton Head non-profit organizations.

Savor delicious home-cooked meals with Sunset Rentals – your home away from home on Hilton Head Island!

The Best Collection of Sea Pines Vacation Rentals

At Sunset Rentals, our properties range from smaller more intimate spaces to large & luxe mansions. For peace of mind, all our properties feature high-security keyless entry, and our premium rentals include luxury linen and towels. Let us help to plan your next Hilton Head Island stay today!

Rent a Boat on Beautiful Hilton Head Island

Hilton Head Island is blessed with 12 miles of coastline along South Carolina’s Atlantic coastline, making it perfect for fishing, boating, and tons of water sport activities. There are various opportunities to boat on several types of vehicles, like kayaks, sailboats, party boats, and even yachts. With six marinas and harbors, you will be kept busy!

Let’s explore some of the best Hilton Head boat rentals:

Island Head
Run by tourists turned locals, Michael and Taylor, Island Head boasts some of the finest Hilton Head boat rentals. Both of them have immense experience in the water sports industry, which reflects in the way they run their company. They are friendly, knowledgeable, and provide the perfect balance of fun and safety.

Anchors Away Sailing Charters
Anchors Away Sailing Charters offers private expeditions for up to six people. You can hop aboard the stunning morning sail, the breezy dolphin watch afternoon sail, or relax while viewing the sunset evening sail. All three sails have different agendas and turn out to be completely different experiences.

Vagabond Cruise
Vagabond Cruise, since 1968, is Hilton Head Island’s original sightseeing and cruise operator. Needless to say, they have tons of experience in this arena and offer some unforgettable cruises on the islands. You can take your pick from holiday cruises, crabbing expeditions, and Savannah Day cruises—amongst the many cruises they offer.

Yacht Club of Hilton Head
Founded in 1971 by a group of sailors, the Yacht Club of Hilton Head is the oldest yacht club on the island. They are a boating and social club, which means that boating enthusiasts on Hilton Island are a part of this club. They provide a variety of boating activities plus a dynamic social calendar.

HHI Vacation Rentals

If you are planning to book a Hilton Head boat rental and stay on the island, then look no further than Sunset Rentals. We provide various types of rentals to suit every family, like pet-friendly rentals, oceanfront rentals, or rentals with private pools.

6 Local Tips for Hilton Head Island

As Hilton Head Island locals, we’ve got all the best local tips up our sleeve! We know all the best places for your next adventure, hidden gems you’ll otherwise pass on by, tips to make the most out of your trip, and all the best places to stay across the island. Don’t just take our word for it, read this guide for the top locals tips you should take advantage of on your next vacation to Hilton Head Island!

1. Best Spots to Catch a Sunset or Sunrise

Shelter Cove Harbour & Marina is located on the Broad Creek, offering a stunning viewpoint with boats coming in and out of the harbor and stunning colors washing across the water. You can watch the sunset from one of the award-winning restaurants, community events throughout the summer, or standing by the marina.

The Harbour Town Yacht Basin is one of the most popular sunset spots on the island, whether from the Yacht Basin with a view of the dolphins, from the pier with a view of the lighthouse, or from the top of the Lighthouse Museum with a view of the whole resort area of Sea Pines.

If you’re looking for an adventure with a view, a sunset cruise is the way to go! There are plenty of companies across the island that offer an exhilarating boat ride through the waterways while you watch the sunset. Just pick the location, book your tour, grab your camera, and head out for the sunset. H2O Sports, Mermaid of Hilton Head, and Vagabond Cruises are just a few of the popular sunset tours.

2. Uncrowded Beaches Away from the Hustle & Bustle

Mid-island beaches away from the main resort areas are uncrowded oases with white sand, sparkling waves, and less crowds. These include Burkes Beach, Driessen Beach, and Folly Field Beach. These hidden gems are perfect for swimming, surfing, bodyboarding, beach picnics, and a scenic, fun-filled family day at the beach.

3. Must-Taste Dishes

With such a wide variety of delicious Lowcountry cuisine, it can be difficult to decide which dish you must try. But don’t worry, we have had plenty of time living here to put together our favorite meals for you to try. 

The infamous Skull Creek Boathouse offers a Boathouse Sampler, perfect to test their delicious coconut almond shrimp, dill pickle chips, calamari, and hushpuppies for yourself- true Southern delicacies. 

The Old Oyster Factory is best known for, you guessed it, their oysters! Enjoy panoramic water views with delicious fresh-caught local oysters that you’ll never forget. It’ll have you coming back to Hilton Head Island year after year, just for the cuisine.

Hudson’s Seafood House on the Docks is one of the only remaining local fishing fleets on the island with fresh-caught fish straight from the docks to your table. Their Atlantic Salmon is a must-try, fresh-caught salmon dish varying seasonally with expert-picked toppings.

4. Ditch the Car, Walk or Bike the Trails!

One of the best ways to explore the island is by walking or biking the trails. Ditch the car, grab your bike or walking shoes, and hit the trails for a one-of-a-kind adventure. On Hilton Head Island, you can walk between resort areas, to the beach, through shopping centers, and more!

Bike through the beach for stunning water views, cool breezes, and white sandy trails. Ride through Shelter Cove Community Park for live music and entertainment along the way. Or head to Fish Haul Creek Park’s 31 acre preserve away from crowds, through wetlands, beach, and forest.

5. Look for Wildlife

The island is teeming with wildlife from alligators hiding in the ponds to pelicans soaring over the waves, everywhere you look is an opportunity for wildlife viewing!

Sea Pines Forest Preserve features 605 acres of ponds and forests covered in Spanish moss, with the opportunity to see turtles, alligators, herons, eagles, snakes, and more on an exhilarating nature walk.

Dolphin tours are a popular favorite to see one of the most magnificent creatures to grace our island! Hilton Head Dolphin Tours, Dolphin Seafari, and Island Explorer are some of the best dolphin tours to encounter dolphins with a tour guide through the waterways guiding you where to look and when to grab the camera!

The beach is another popular exploration spot with plenty of viewing spots for dolphins, starfish, pelicans, sand dollars, jellyfish, crabs, and more!

6. Get out on the Water

Ditch the car, bike, and walking shoes for an even better adventure– one on the waterways! Whether by kayak, paddleboard, private boat, or fishing charter, there are endless opportunities to explore the water on Hilton Head Island. 

Rent kayaks, paddleboards, skim boards, and more for the adventure of a lifetime with the whole family. Looking for more of a guided tour with a fishing guide or wildlife expert? You’re in luck! The island also offers plenty of guided tours with local experts to get you off the land and onto the water.


The Best Places to Stay in Hilton Head Island

At Sunset Rentals, our vacation rentals are all based in Hilton Head, South Carolina. We have some fantastic properties fit for groups of all sizes. We offer luxurious vacation rentals to fit every family’s wants and needs to make their vacation a breeze. With unique accommodations and a wide range of convenient amenities, you’re sure to find something you’ll love. We offer private homes and villas across the island and first-class service to all of our guests.