Hilton Head vacation rentals place you at the center of South Carolina’s low country charm and beauty while offering an endless array of tours, attractions, and restaurants. The island has so many fun activities for the whole family, finding time to tackle them all is the biggest challenge. It’s a big plus that Hilton Head has magnificent coastal weather, alluring green spaces, friendly people, and engrossing things to do. Here’s our list of the top 10.

1. Feel the Spirit of Harbour Town


Get to know Hilton Head with a Historic Savannah Cruise or a Sunset Dinner Cruise aboard the Spirit of Harbour Town, a luxury passenger yacht. The yacht is itself a local attraction because it’s essentially a floating restaurant with a full bar, wait staff, crew, captain, and an award-winning chef specializing in fine contemporary low-country cuisine. There is a kids’ menu as well. Locals rave about the Michelin-quality food, the sumptuous decor, the outdoor seating, and the 20-square-foot-sized panoramic windows on the main deck.

2. Roll Through Hilton Head on a Segway

Whiz through Hilton Head atop a Segway, one of the most exhilarating ways to see more in less time. ProSegway offers slow-paced eco tours of Hilton Head’s scenic pathways and Honey Horn, a Smithsonian-affiliated nature preserve. Tours range from 75 to 100 minutes, and kids are welcome to join in.

3. Step Back into Hilton Head’s History

See how Native Americans and early settlers thrived on Hilton Head during eras past. Legacy History Tours commands a team of expert guides steeped in local history. Choose between themed tour packages, such as Single Site Intensive, Early Explorers, and Civil War Era. Legacy History Tours hosts single-vehicle small groups, families, or multi-vehicle large groups. It also provides customized tours as well as tours of surrounding areas, including Santa Elena and Fort Pulaski, a Civil War fort.

Find the perfect Hilton Head Island vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Take the High Road With a Helicopter Tour

Relish a bird’s-eye view of Hilton Head and the Carolinas with Hilton Head Helicopter Tours, a local family-owned helicopter tour company. Choose from a handful of curated itineraries and themes, such as ecology, adventure, island-hopping, and beaches. Each tour takes a unique route over Hilton Head and its environs, and the company can accommodate families and large groups.

5. Layer on the Deliciousness at Stack’s Pancakes

Your vacation rental is your home away from home, but you’re on vacation, so treat yourself to a world-class breakfast at Stack’s Pancakes. They serve Southern-style breakfast and brunch all day long in a laid back, fun, welcoming atmosphere. The menu emphasizes pancakes of all kinds, but you’re more than welcome to sample the chicken and waffles or split the crepes with friends and family.

6. Gallop Into Great Fun With a Horseback Riding Tour

Lawton Stables is your guide to the low country’s impressive network of tranquil, gorgeous trails. Tucked between palmettos and moss-shrouded oaks, Lawton Stables specializes in Western-style one-hour guided horseback tours for the whole family and kid-friendly pony rides. It also maintains an open-to-the-public animal farm. You can purchase feed to share with the resident ponies, chickens, alpacas, pigs, miniature donkeys, sheep, and goats.

7. Set Sail in Search of Treasure with Pirates HHI

Pirates HHI oversees mock pirate hunts for treasure buried off the coast of Hilton Head. This is essentially a pirate-themed cruise, and locals say it’s one of the best things to do with kids. Kids under 2 ride for free. The pirate fleet consists of the Smelly Sam and the Black Sparrow. Once aboard, kids get face paint, a temporary pirate tattoo, and costumes, and they learn how to talk like pirates. The promised treasure is real and edible, but it changes from hunt to hunt.

8. Taste Hilton Head’s Fruit of the Sea

Experience the quintessence of “fresh catch” at The Crazy Crab, located directly on the Hilton Head waterfront. Two locations cater to locals and visitors, serving up lunch, dinner, and a kids menu. Ingredients are locally sourced, and the menu selections cover all bases for seafood lovers, from oysters and crabs cooked every which way, steamed shellfish, and lobsters to broiled or fried seafood, steak, chicken, and pasta. According to locals, this is the best place in town for crab legs.

9. Make the Low Country High with a Zipline Tour

ZipLine Hilton Head is a new Hilton Head attraction that’s quickly becoming one of the most popular things to do. The company delivers canopy tours of Hilton Head’s stunning wooded areas, trails, and waters. The company’s titular tour runs roughly two and a half hours. It consists of eight ziplines at heights up to 75 feet, a dual-cable racing zipline finale, and aerial staircases and suspended bridges in between. The tour zips over the dolphins, marshes, and boats near Broad Creek Marina Adventures.

10. Mini-Golf at Adventure Cove

Get lost on the 18-hole mini golf courses at Adventure Cove, Hilton Head’s location for retro video arcade games and mini golf. Paradise Falls and Lost Lagoon, the two mini golf courses, feature diverse man-made terrain that wends through caves, rainforests, and up and down stairs. In the video arcade game room, win tickets that you can redeem for popular consoles and peripherals, such as Beats headphones, XBox, and PlayStation.

Ready to go? Check out these amazing Hilton Head Island vacation rentals on Tripping.com.