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A Visitors Guide to Shopping on Hilton Head Island

There are so many reasons to visit Hilton Head Island, it’s no surprise our slice of paradise is consistently voted one of the world’s favorite islands and the top island in the US. The top attraction that draws visitors from around the globe to Hilton Head is the stunning natural setting with pristine sandy beaches, scenic waterways, lush wildlife preserves and secluded outdoor activities. But there’s more! 

The appeal of the natural beauty of Hilton Head Island is enhanced by the luxury plantations, quaint villages and scenic marinas with an abundance of eateries serving the finest Lowcountry seafood and southern fare and upscale shopping destinations for the ultimate shopping experience on Hilton Head.   

Slow down your pace, switch to island time and indulge in some family-friendly retail therapy and island style shopping on Hilton Head Island. Whether you’re shopping for necessities, picking up fresh produce or seafood from a market or searching for a unique Hilton Head souvenir or gift to take home, you’ll find it all on Hilton Head Island.

Coligny Plaza

Slip away from the beach for a one-of-a-kind shopping spree at Coligny Plaza, Hilton Head’s favorite shopping destination since 1955, just steps from the ocean. The Coligny Plaza is located oceanfront in Hilton Head’s downtown Forest Beach area and has everything you need for your Hilton Head Island vacation with the best shopping on the island. Coligny Plaza welcomes beach-goers for a laid-back shopping experience at over 60 specialty stores and fun outdoor kiosks, with year-round entertainment and the best oceanfront dining on Hilton Head. 

Shelter Cove 

Shelter Cove is Hilton Head’s premier waterfront shopping destination, just off the Intracoastal Waterway across from Palmetto Dunes Oceanfront Resort. The Shelter Cove Harbour & Marina is a hub of activity with cruises and nature tours, water sports, fishing charters, live entertainment, fun festivals and Mediterranean-style island style shopping. Browse the boutiques, gift stores and the eclectic Nash Gallery along the harbour side promenade, then make your way to the nearby Shelter Cove Town Center. 

Shelter Cove Town Center is Hilton Head’s newest shopping attraction with an open-air waterfront village, palmetto lined walkways and tranquil views of Broad Creek and the Lowcountry marshlands. With over 30 charming boutiques, specialty stores, enticing eateries and a community park and playground for the kids, you can shop to your hearts content at Shelter Cove. 

The Harbour Town Shops at Sea Pines 

The Harbour Town Shops are located in the upscale Sea Pines Plantation, home to the Hilton Head’s legendary landmark, the candy-cane Harbour Town Lighthouse. The Harbour Town Shops offer visitors to Hilton Head a leisurely shopping experience surrounded by the scenic Harbour Town marina scattered with luxury yachts, sailboats and over 20 boutiques, galleries, gift shops, coastal treasures and unique dining experiences. Climb to the top of the lighthouse for the perfect souvenir and lasting memories of your vacation from the Harbour Town Lighthouse Museum and Gift Shop. 

Main Street Village

Step back in time with an old-fashioned shopping experience in Hilton Head’s Main Street Village, home to the island’s oldest and traditional family-owned stores. The quaint shopping area has tree-lined walkways with unique shops and some of the best restaurants in Hilton Head. There’s no big-box stores on Main Street, just a small town island shopping experience.

Tanger Outlets Hilton Head

Go for the big savings on designer brands at the Tanger Outlet Stores, just over the bridge in nearby Bluffton, SC. Hilton Head’s Tanger Outlets has a variety of over 90 top outlet stores, curbside pickup if you choose to avoid the crowds and a variety of onsite restaurants and eateries. For trinkets and treasures,  stop by the quaint shops in Old Town Bluffton before heading back to the island. 

Hilton Head Island Seafood & Farmers’ Markets 

Your island shopping experience on Hilton Head is not complete without a visit to a local farmer’s market, the perfect place to pick up fresh, local produce and savor the flavors of the Lowcountry with a home cooked farm-to-fork meal in the comfort of your Hilton Head vacation home.

Stay with Sunset Rentals!

Sunset Rentals represent over 225 of the most trusted vacation rentals in the top resort areas of Hilton Head. From the shores of the pristine Atlantic coastline to the rolling fairways of Hilton Head’s award-winning golf-courses, our vacation rentals are perfectly placed to experience Hilton Head Island’s top attractions and world-class shopping destinations.

Browse our rentals on Hilton Head Island online, book direct or call our on-island team on (800) 276-8991 today to guide you to the idyllic home-away-from-home on Hilton Head Island.

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5 Tips For Hosting a Family Reunion on Hilton Head

Situated only 30 miles from historic Savannah Georgia, Hilton Head Island boasts a stunning and serene seaside location, welcoming southern charm, a relaxed Lowcountry lifestyle, and a wide range of family-focused activities and vacation homes that appeal to guests of every generation.  

Not only is Hilton Head the “#1 Island in the Continental US”, but it has also been named the “Best US Beach for Families” by Parent Magazine and is a destination geared for sun, fun, and fabulous beach family reunions – that may just turn to family tradition! Hilton Head Island is also a very dog-friendly destination! Yes, Fido can visit the island’s top tourist attractions, restaurants, and beaches too! 

Planning a successful family vacation is tricky enough, trying to coordinate a destination family reunion that puts a smile on everyone’s dial, from the tiniest tots to the great-grandparents, can be downright intimidating! 

Our local team at Sunset Rentals has been welcoming family groups of all sizes to the island since 1993, and we know a thing or two about hosting a family reunion on Hilton Head Island. We’ve put together our top 5 tips for hosting a family reunion on Hilton Head Island, and have a treasure trove of local tips and recommendations in our Hilton Head Island travel blog to help plan a successful reunion.

1. Select Your Season

The weather on Hilton Head Island is beautiful year-round and we have some of the warmest ocean water on the Atlantic Coast! The official beach season (and peak season on Hilton Head) is April 1st through September 30th and May through October is prime sea turtle season, an easy way to entice the family to a reunion on Hilton Head Island. The summer season tends to be hot and humid with temps between 86oF and 92oF and the winters are mild, rarely dipping below 60oF. 

How you select the season for your reunion depends on your family style and preference – hot, summer beach days, cooler weather and fewer crowds out of season, or a winter snowbird family reunion at the beach! Be aware that many of the island’s outdoor outfitters close for a period during the winter season, so do your activity research in advance. 

2. Decide Where to Stay on Hilton Head

Hilton Head Island is divided into unique gated communities, known as resort areas of plantations, with an Infinite choice of accommodation available in each resort area community. Palmetto Dunes and Sea Pines Resort are particularly popular with families, Shipyard and Port Royal are quieter neighborhoods, and Forest Beach lies in the heart of the action, within walking distance to Hilton Head’s downtown area activities, Coligny Plaza shops and restaurants, and the shoreline of the award-winning Coligny Beach Park. Wherever you decide to stay on Hilton Head, the island’s beautiful beaches are within easy reach on the network of trails connecting every resort area. 

3. Arrange Your Island Activities In Advance

Planning activities for a big group can be challenging, but Hilton Head Island’s extensive activity offerings appeal to young and old alike! Balance your days between beach play, water activities, golf and racquet sports, cultural experiences, and eco-friendly nature tours unique to South Carolina’s Lowcountry barrier islands. Hilton Head is a popular destination, be sure to plan and book your tours and activities well in advance to avoid disappointment!  

  • Hilton Head Island has over 60 miles of leisure paths winding through the island for fun family bike rides, gentle strolls for the older folk, and some of the best wildlife viewing on the island!  
  • The island boasts 12 miles of Atlantic shoreline with easy access to long wide stretches of white sand beaches, beautiful boardwalks through tidal marshes and sand dunes, seasonal lifeguards, excellent amenities, beach gear rentals, and everything the family needs for a day at the beach! Check out our complimentary bike and gear credit program! 
  • Every watersport imaginable is available on Hilton Head Island – sailing, stand-up paddle boarding, kayaking, canoeing, wakeboarding, tubing, jet skiing, parasailing, relaxing boat rides, and even pirate or mermaid adventures for the kids. Our Vayk Gear credit program includes kayak and paddleboard rentals too! 
  • Guided fishing charters are a family reunion favorite on Hilton Head! Whether you’re a family of avid anglers, or new to the sport, you’ll find a family-friendly fishing charter to accommodate the whole crew, even Fido! 
  • With 24 lush golf courses and more than 500 courts for tennis or a family round of pickleball, Hilton Head is a paradise for sports-loving families. Each HHI resort area has its own golf and racquet sports facilities, so plan your sports activities accordingly!  
  • Plan for rainy day activities or a break from the sun! For indoor entertainment, the kids love exploring the Children’s Sandbox Museum, Adventure Cove, and the Kids Zone at the Coastal Discovery Museum. And, Hilton Head Island has endless retail therapy and restaurants to lure you away from the beach.    
  • From foodie festivals, cultural celebrations, and fabulous summer events at Shelter Cove and under the famous Liberty Oak at Harbour Town, there is always something happening on Hilton Head Island! Once you select your season and pick your family reunion dates, check the local Hilton Head Island events calendar to plan your family reunion events and festivities. 

4. Plan Crowd-Pleasing Meals

Putting together a meal plan and deciding when to eat out and when to dine in for a family reunion is no easy feat! Now you’ve chosen your favorite Hilton Head resort area and arranged your activities, meal planning is a whole lot easier knowing where you’ll be and when. With 250+ restaurants and unique Lowcountry dining experiences on Hilton Head Island, you’re spoilt for choice. 

From Coligny Plaza, Harbour Town at Sea Pines, and Shelter Cove to Hilton Head’s golf clubs and luxury resort hotels, there are hundreds of cafes, restaurants, breweries, and bars scattered around the island catering to every group size, style, and budget! 

Depending on the size and scope of your family reunion, cooking and sharing meals at your vacation rental may be the smart way to keep costs low, and drama limited! Appoint a family reunion meal planning committee, arrange backyard BBQs and Lowcountry Boils, shop the farmers’ markets for fresh local produce, and enjoy the perks of a full kitchen that caters to large group gatherings with the chance to share meals together, at home!

5. Create Memories with Sunset Rentals

Sunset Rentals represents over 220 of the finest vacation rentals on Hilton Head ranging from luxury 7-bedroom pool homes to keep the family together under one roof to resort complex communities with private condos and villas to carve out your own personal space and gather together in communal areas. 

Our group friendly vacation rentals feature a host of high-end amenities to ensure your family time together is as memorable as it is meaningful, and our selection of pet-friendly rentals on Hilton Head Island means there’s a place for your pup too! 

Start planning your Hilton Head family reunion today with our worry-free and flexible Sunset Package or give our vacation specialists a call at (800) 276-8991 to match your family with the perfect HHI reunion rental. 

Spend the Holidays in Hilton Head Island

Sunset Rentals offers offers 225+ of the finest Hilton Head Vacation Homes and Villas. Explore all of our vacation rentals or give us a call today at 1-800-276-8991 to book your stay to the island!

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Top 4 Golf Courses On Hilton Head

Just because it’s winter in Hilton Head Island doesn’t mean you can’t play golf. While courses around the country close for the season, Hilton Head’s famous golf courses remain open. So, if you’re visiting Hilton Head Island in winter and want to hit the links, where should you go? The team at Sunset Rentals has some ideas. Here’s our list of the best courses to play in Hilton Head on your winter golf trip.

1. Atlantic Dunes

Sea Pines Golf Course

Atlantic Dunes is the oldest golf course in Hilton Head, but it remains one of the best. Of all of the courses in Hilton Head, only two have oceanfront holes, and Atlantic Dunes is one of them. Be prepared to lose a few balls in the water; many of the holes feature water hazards. Overall, Atlantic Dunes is a challenge for golfers of all skill levels, but it’s a gorgeous course well worth visiting.

100 N. SEA PINES DRIVE, HILTON HEAD ISLAND, SC, 29928

(843) 842-1477

  • 7,065 Yards
  • 74.3 Rating
  • 143 Slope
  • 72 Par

2. Harbour Town Golf Links

Sea Pines Golf Course

“Iconic” is how three-time U.S. Open Champion Hale Irwin describes Harbour Town Golf Links, and it’s hard to disagree. You might recognize the red and white striped lighthouse that backdrops this course; it’s quite famous. Harbour Town Golf Links is a favorite among PGA Tour players, and it’s not hard to see why; it’s a beautiful-looking course that features a series of world-renowned par threes. Plus, this course is more fun and playable compared to other upper echelon golf courses.

11 LIGHTHOUSE LN, HILTON HEAD ISLAND, SC, 29928

(843) 842-1904

  • 7,000 Yards
  • 75.6 Rating
  • 148 Slope
  • 71 Par
Plan Your Trip to Sea Pines

3. George Fazio Golf Course

Palmetto Dunes Golf Course

George Fazio Golf Course is Hilton Head Island’s only par-70 public golf course, and it is a beauty. George Fazio Golf Course is considered by many to be the most challenging public course on the island, but it is still an exceptional experience for golfers of all skill levels. The course only has two par fives, while the majority of the course features long par fours. George Fazio Golf Course is an excellent option if you’re looking for a challenging course with immaculate greens.

7 Carnoustie Road, SC 29928

(888) 909-9566

  • 7 a.m. – 8 p.m.
  • 18 HOLES
  • 70 PAR

4. Robert Trent Jones Oceanfront Golf Course

Palmetto Dunes Golf Course

If you want to play a round at a course on the oceanfront, look no further than Robert Trent Jones Oceanfront Golf Course. What makes this golf course one of the best courses on Hilton Head? The 10th hole is stunning; on elevated greens, golfers enjoy panoramic views of the Atlantic Ocean. There are also the ever-shifting winds to account for, which means golfers must approach each hole differently. Robert Trent Jones Oceanfront Golf Course is truly unique and is sure to be a memorable experience for all players.

7 Trent Jones Lane, SC 29928

(888) 909-9566

Plan Your Trip to Palmetto Dunes

Stay at a Luxury Hilton Head Vacation Rental

Stay in close proximity to all of the best golf courses in Hilton Head with one of Sunset Rentals’ luxurious vacation rentals. We have a variety of vacation rentals, including oceanfront options. To book your stay with us, please give us a call at 843-785-6767 or check availability online.

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9 Fun Summer Festivals On Hilton Head 2023

Hilton Head Island, SC hosts a range of popular festivals that draw many thousands of visitors to the island every summer. The Island’s event calendar includes local arts, nightlife, family activities, festivals, and much more. The team at Sunset Rentals has compiled a list of our favorite upcoming events on Hilton Head Island. Be sure to check some out during your getaway to the stunning shoreline of South Carolina!

1. Coligny Plaza Summer Music Series


LOCATION: Center Stage at Coligny Plaza

DATE: May 27, 2023 – September 4, 2023

TIME: 6:30 PM to 8:30 PM 

ADMISSION: FREE!

2023 SCHEDULE OF EVENTS
Sunday, Wednesday & Friday – Jevon Daly
Monday – John Cranford and Friends
Tuesday – Kyle Wareham
Thursday – Nick Poulin
Saturday – Mike Kavanaugh


The Coligny Plaza Summer Music series takes place on the Center Stage every night throughout the summer season. The series is family-friendly and the perfect way to end a day on Hilton Head’s award-winning beaches! Coligny Plaza has a wide selection of restaurants to grab a bite to eat and iced summer cocktail or cold brew, before or after the show!

2. Greg Russell Concert


LOCATION: Liberty Oak, Sea Pines Harbour Town 

TIME: 8 PM to 9:30 PM

ADMISSION: FREE! Visitors not staying within the Sea Pines Resort Area are required to pay a small, cash entry fee at the Sea Pines gate. 

2023 SUMMER SCHEDULE 
May 26 to May 28 – Friday to Sunday
May 31 to August 11 – Monday to Friday
August 14 to August 25 – Monday, Wednesday & Friday
August 31 – September 3 – Labor Day Weekend


Greg Russell is a nationally renowned singer-songwriter and a Hilton Head Island icon! His summer shows under the famed Liberty Oak in Sea Pines Harbour Town have been delighting visitors to Hilton Head for over 40 years. Join us this summer for family-friendly entertainment, sing-alongs, storytelling, and true Southern hospitality with Greg Russell.

3. Shelter Cove HarbourFest


LOCATION: Shelter Cove Harbour & Marina

DATE: Memorial Day – Labor Day

ADMISSION: FREE!

SCHEDULE OF EVENTS

2023 HabourFest Fireworks Schedule: 
Time: Just after dark!
Tuesdays: June 6, 13, 20 & 27
Tuesdays: July 4, 11, 18 & 25
Tuesdays: August 1, 8, 15 & 22

2023 Live Performance Schedule:

Shannon Tanner  
Time: Shows at 6:30 PM and 8 PM 
Memorial Day Weekend: Saturday, May 27 & Sunday, May 28
Monday – Wednesday | May 29 – August 23
No shows August 25 – September 1 

Cappy the Clown 
Time: 6 PM to 9 PM 
Memorial Day Weekend: Saturday, May 27 & Sunday, May 28
Monday – Friday | May 29 – September 1
Labor Day Weekend: Saturday, September 2 & Sunday, September 3

Parrot Palooza Sunset Celebration 
Time: 7 PM 
Thursdays: June 15, 22 & 29
Thursdays: July 6, 13, 20 & 27
Thursdays: August 3, 10, 17 & 24
Labor Day Weekend: Saturday, September 2 & Sunday, September 3


The HarbourFest at Shelter Cove Harbour & Marina on Hilton Head Island is a weekly celebration during the summer with live music and entertainment, arts and crafts, kids’ activities, and weekly fireworks every Tuesday just before dark. Celebrating 34 years, HarbourFest is a magical summer experience on Hilton Head Island.

4. Shelter Cove Summer Jams


LOCATION: Shelter Cove Community Park

DATE: June 13 to August 8, 2023
Tuesdays: June 13, 20 & 27
Tuesdays: July 4, 11, 18 & 25
Tuesdays: August 1 & 8

TIME: 5:30 PM TO 9 PM

ADMISSION: FREE!


If you’re traveling to Hilton Head this summer with children, Summer Jams is a can’t-miss weekly event at the Shelter Cove Community Park. The kids can play in bouncy houses and dress up with face painting, while you relax listening to local live music in your lawn chair! After a few hours of fun, the evening will end with the fabulous fireworks display that takes place every Tuesday at Shelter Cove HarbourFest.

5. Party in the Park & Maker’s Fair


LOCATION: Lowcountry Celebration Park

DATE: Thursdays, June 22 to July 27, 2023

TIME: 5:30 PM to 8 PM 

ADMISSION: FREE!


Enjoy family happy hour for a month of Thursdays at Lowcountry Celebration Park near Coligny Beach Park and Plaza. This fun summer event combines local live music with amazing Lowcountry food and beverage vendors, arts and crafts, and the park playground with bouncy houses for the kids. Pop by Party in the Park & Maker’s Fair for a fun family night out and local shopping for one-of-a-kind gifts and souvenirs!

6. Rock N Ribs 2023


LOCATION: Coligny Plaza

DATE: Friday, October 20 – Saturday, October 21, 2023

2023 SCHEDULE OF EVENTS:
**Save the date and sign up for email updates and ticket sales HERE!


Rock N’ Ribs is one of Hilton Head’s best live music festivals – a weekend of classic rock n’ roll with a side of delicious southern-style barbeque! The weekend schedule includes world-class live music, Pitmaster Ocean Olympics on Coligny Beach, barbeque tasting events, and Sunday brunch & blues at the Beach House. Rock N’ Ribs sells out fast!

7. Concours d’Elegance & Motoring Festival


LOCATION: Port Royal Golf Club, Hilton Head Island

DATE: Friday, November 3 – Sunday, November 5, 2023

ADMISSION: Purchase tickets HERE!

**Discounts are available through September 30, 2023

VIP Packages available online
Daily Adult Admission: $85
Weekend Adult Admission: $140
Student & Active Duty Military: FREE

PARKING: Complimentary parking at the Hilton Head Island Public School Complex

SHUTTLE: Continuous shuttle service (with wheelchair access) on Saturday & Sunday

2023 SCHEDULE OF EVENTS:
Friday 7 PM to 10 PM – Flights & Fancy Aeroport Gala
Saturday 9 AM to 4 PM – Car Club Showcase
Saturday 9 AM to 4 PM – Aero Expo 
Saturday 9 AM to 4 PM – Southern Grand Classic Presented by Classic Car Club of America
Saturday 4 PM to 6 PM – Motoring Festival After PartySunday 9 AM to 4 PM – Hilton Head Island Concours d’Elegance


The Concours d’Elegance & Motoring Festival on Hilton Head Island is a world-class event with traditional southern flair.  This popular event showcases a rare collection of automobiles, airplanes, and motorcycles with the best of the best in automotive exhibitions, racing, dining experiences, and a luxury lifestyle on Hilton Head.

8. Hilton Head Oyster Festival


LOCATION: Shelter Cove Community Park & Lowcountry Celebration Park

DATE: Friday, November 10 – Saturday, November 11, 2023

2023 SCHEDULE OF EVENTS:
**Get notified about 2023 ticket sales and schedule of events HERE!


The Hilton Head Oyster Festival is a magnificent celebration of oysters and local Lowcountry culture. Try boiled oysters, fried oysters, stewed oysters, and more. This November, sit back and enjoy live music, a football viewing area, wine, and buckets of freshly shucked oysters at this can’t-miss fall event on Hilton Head Island.

9. Hilton Head Island Wine & Food Festival


LOCATION: Multiple locations on Hilton Head Island

DATE: Event Passed! Save the date for March 2024


Hilton Head’s wine and food enthusiasts created a week-long celebration to embrace the fruits of global wine partnerships, signature Lowcountry cuisine, and grassroots cultural happenings. At Hilton Head Island Wine & Food Festival, you’ll find exceptional wine dinners and educational seminars, plus the traditional grand tasting and well-loved public tasting.

STAY WITH SUNSET RENTALS!

Now that you’ve chosen which events you want to attend, it’s time to find your Hilton Head rental. Sunset Rentals provides various types of rentals to suit every family, like pet-friendly rentals, oceanfront rentals, or rentals with private pools. We are driven by the desire to make certain that your vacation is spent enjoying that time. We are a locally operated Hilton Head Island company that takes pride in offering first-class service to our guests.

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Explore all of our Hilton Head Vacation Rentals or give us a call today at 1-800-276-8991 to book your stay.

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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.

HOW IT WORKS

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!

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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.

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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.

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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.

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How To Rent Jet Skis On Hilton Head Island?

While it won’t be easy to pry your family from Hilton Head Island’s sandy beaches and pristine golf courses, there’s nothing quite like an aquatic adventure in Calibogue Sound, a salty bottlenose dolphin haven. There are countless ways to explore the Sound, including a dolphin safari, sky-high parasailing voyage, and chartered fishing trip. However, there’s nothing quite as action-packed as hopping aboard a speedy jet ski rental in Hilton Head Island and blazing through Calibogue Sound. This oceanic waterway features plantations, islands, and, of course, a bevy of underwater critters.

Finding a Jet Ski Rental in Hilton Head Island

Locating a jet ski rental in Hilton Head Island isn’t overly challenging as there are a handful of outfitters within minutes of Sunset Rentals’ fleet of South Carolina beach condos. That being said, wave runners are only available via reservation. Thus, we highly recommend reserving your ride several weeks in advance, if possible. The Sunset Rentals team has strong relationships with several water sports companies, including the three listed below. In alphabetical order, here the three best jet ski rentals in Hilton Head Island. 

H2O Sports
Harbour Town’s H2O Sports is a natural place to start as this long-standing establishment offers everything from alligator tours to sailing charters and, yes, jet ski rentals in Hilton Head. After a brief instruction (this pre-arrival safety video also helps), families can instantly throttle into Calibogue Sound, unlike other land-locked outfitters. Thus, there’s no need to worry about no-wake zones. H2O Sports boasts an expansive fleet of brand new Yamahas, as new additions are added every season. This lovely stretch of the Sound is home to several families of dolphins and sea turtles, so keep your eyes peeled! H2O is also the only company in town to offer GoPro video packages—a priceless keepsake, especially if you stumble upon a friendly bottlenose.

One Hilton Head Island
One HHI is best known for its knowledgeable, welcoming guides, who lead trips through Broad Creek and into the aforementioned Calibogue Sound. Fifteen minutes is added to these semi-guided excursions to account for the short jaunt through Broad Creek’s no-wake zone, where, as you might imagine, many dolphins gleefully explore the aquatic terrain. Travelers often marvel that One’s jet ski rentals in Hilton Head go from zero to 30 mph in only two seconds! It’s also worth noting that jet skiing is a sublime way to avoid crowds, especially during these unique times.

Sea Monkeys Watersports
There’s just something undeniably memorable about choosing a small, family-owned business, such as Sea Monkeys. Sea Monkeys’ team is a tad more personable than other outfits, as they wave “switching fees,” provide military discounts, and are happy to snap free photos. A certified instructor escorts each 75-minute adventure from Hilton Head Harbor to a designated area, where the three-seaters (a rarity) can blaze through the teal sea with nary a care in the world. Because Sea Monkeys offers three-seaters, Mom or Dad can ride with two kids at once!

Luxurious Hilton Head Rental Homes

Sunset Rentals is proud to manage one of the area’s largest collection of Hilton Head vacation homes, ranging from a Folly Field Sandcastle to an Epic Beach House and a Luxury Crabline. On-site luxuries typically include a private pool, beach access, a chef’s kitchen, water views, a spacious deck, and a fireplace. Much like hand-selecting your “forever home,” browsing through our Hilton Head homes is undeniably exhilarating. We have no doubt that you’ll find one that perfectly suits your family’s size, style, and budget.

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How To Go Parasailing on Hilton Head Island?

South Carolina’s picturesque Hilton Head Island remains an aquatic wonderland, especially for those with a penchant for oceanic thrills. Within minutes of arrival, travelers can swiftly hop aboard a speedy wave runner, join a dolphin tour, and hook a jumbo Spanish mackerel deep at sea. However, nothing tops the sheer exhilaration of parasailing in Hilton Head Island, especially when you choose a Sunset Rental-approved outfitter, such as Sky Pirate Parasail.

The Thrill of a Lifetime: Parasailing in Hilton Head

Contrary to popular belief, parasailing in Hilton Head caters to nearly every age group, including kids six and up. While you’re floating 500 feet above the turquoise Atlantic, you’ll obtain unobstructed, jaw-dropping views of the island, spanning approximately 25 miles inland or seaward. Sunset Rentals of Hilton Head recommends three local parasailing gurus, all of which lie a short distance from our finest vacation homes.

Sky Pirate Parasail
The folks at Sky Pirate operate out of Broad Creek Marina, located inside a still, meandering Intracoastal waterway. The marina itself plays host to kayaking outfitters, fishing charters, and a popular pub. Sky Pirate’s state-of-the-art, 12-passenger vessel boasts an 800-foot line, so get ready for some serious airtime. When you’re not suspended 500 feet in the air above Calibogue Sound, you’ll likely spot curious dolphins, pearly egrets, and oceanfront plantations.

Island Head
Island Head’s 90-minute parasail costs a mere $79 per person. The Island Head team emphasizes the surrounding beauty, including Harbour Town Lighthouse, Daufuskie Island, and the sprawling Lowcountry. Flights typically last anywhere between eight and 10 minutes, which is the industry average—just be ready to make a splash at the tail-end of your voyage!

H2O Sports
H20 Sports is based out of the Harbour Town Yacht Basin, an idyllic slice of the island where travelers flock for golf, sea-based adventures, sailing, and coastal cuisines. And H2O knows a thing or two about aquatic thrills, as they offer everything from wakeboarding to alligator tours and old-fashioned parasailing in Hilton Head Island. They offer “the best view of the island”—a true bird’s eye view at scorching (yet safe) speeds. It’s worth noting that H2O offers the cheapest “observer rides” for those afraid of heights but still want to motor through Calibogue Sound.

The Finest Hilton Head Rentals

After each full day of championship golf, offshore fishing, and parasailing in Hilton Head Island, retreat to your luxurious, comfortable vacation home for an evening to remember. We proudly boast one of the island’s largest selections of coastal South Carolina vacation rentals, including the heavenly, pet-friendly Deer Run and expansive, ocean-view Guscio Way. With nearly 250 rental homes in Hilton Head Island, you’re bound to find one that perfectly suits your group’s size, style, and budget. Luxuries include private pools, beach access, chef’s kitchens, lavish outdoor patios, and floor-to-ceiling fireplaces.

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Sunset Rentals
21 New Orleans Rd
Hilton Head, SC 29928
info@sunsetrentals.com 800-276-8991 843-785-6767

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