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Has it been too long since the whole family got together? Plan a Hilton Head family reunion to unite the entire crew for some time away together. We’re here to offer advice, tips, and information to create the best possible family vacation. Use our guide here to plan for activities, things to do, grocery services, dining options, and other concierge services, as well as tips for finding the most ideal vacation rental in Hilton Head for your family reunion. 

Hilton Head Family Reunion Planning Guide & Tips

#1 Find the Best Time for Everyone


The first step in planning the perfect family reunion is to find a time that works for everyone. Schedules get busy quickly, so it’s best to think ahead when planning. If your family has a lot of kids, chances are that spring break or summer are going to be the best times to plan. An easy way to poll the whole group is to use a tool like Survey Monkey or Google Forms to get feedback on dates.

These tools can also be helpful to determine proper headcount, dining preferences, plan out things to do, and even narrow down cost estimates.

#2 Secure An Accurate Headcount & Confirm Costs

big family on beach

Prior to booking a vacation rental, you need to get a final headcount from the group and confirm the costs for everyone. Since costs can waver significantly if a group drops out, it’s important to keep everyone aware and accountable before booking.

Be sure to check the number and type of beds in each rental to be sure you’re accurately accounting for children, couples, and single adults.

#3 Book the Perfect Hilton Head Vacation Rental

hilton head vacation home

Now that you’ve found a date that works for everyone, gotten an accurate headcount, and determined cost per-person, it’s time to book your vacation rental. We offer a wide variety of Hilton Head vacation rentals for large groups as well as homes with a private pool, dog-friendly properties, oceanfront homes, and more. Our vacation rentals can accommodate up to 22 people, and we also have many neighboring homes if you’d prefer to split into two nearby houses or have an even larger group of people joining.

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#4 Plan Out Activities and Things to Do

family in kayaks

We know it can be challenging to plan for big groups, but there are so many family-friendly things to do in Hilton Head for all ages. You can visit the island’s many beaches, parks, and preserves and explore Hilton Head’s iconic Lowcountry landscape at your leisure. Here are a few of our favorite activities for big groups:

Let the Beach Play Company plan a day of fun for your group. This company offers customized beach party days with games and activities for a minimum of two hours for 16 guests. You can add on to include more people or spend more time at the beach as well.

Fishing is hugely popular in the waters of Hilton Head, and you can book a charter that takes you out into the Atlantic Ocean or Intracoastal Waterway for an afternoon. Fishing charter companies typically supply the necessary equipment so your group can just show up and be ready for a day on the water.

Kayaking is a great way to view dolphins, aquatic birds, and other wildlife, and it’s easy enough for all ages. Most companies offer guided tours and lessons to accommodate your needs and tailor your experience.

Enjoy biking on Hilton Head Island. Hilton Head is a very bike-friendly community, and there are tons of trails to explore on the island. You can bike to visit historic sites, community parks, and beaches.

Don’t forget when you book your rental with Vacation Homes of Hilton Head you receive the Southern Hospitality Pass, which includes free bike rentals and access to golf and miniature golf courses.

Hilton Head Things To Do

#5 Make Dining Plans For Your Group in Hilton Head

family eating dinner outside

All of our Hilton Head vacation rentals are equipped with a full kitchen to make cooking for groups a breeze. We offer grocery delivery services so you don’t have to worry about wasting precious vacation time at the store. Low Country Grocery Runner will have all your needed supplies ready and waiting for you in your vacation rental. You can also take advantage of personal chef services or a family cooking class while you’re here.

There are also plenty of great dining options in Hilton Head for large groups.

Poseidon Coastal Cuisine is located mid-island and offers a menu of creatively crafted steak and seafood dishes, cocktails, and more. This spot also features a raw bar, rooftop, and great happy hour deals. Their menu is pretty extensive so everyone in your group will find something they love.

Marley’s Island Grille offers casual, coastal cuisine that truly makes you feel like you’re on island time. There’s, of course, a wide selection of fresh seafood, and the menu features plenty of items for the non-seafood lovers in the group as well. Marley’s is the place to go for quintessential tropical cocktails as well.

Frankie Bones features a delicious menu of steaks, seafood, pasta, and more. Indulge in the hand-shaken martinis and award-winning wine list for dinner, or come for their popular Sunday brunch. This classic lounge creates delicious pasta, seafood, flatbreads, soups, salads, seafood, sandwiches, and more. Everyone will find something they love here.

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Create Your Hilton Head Family Reunion Now