Large Family Vacations: A New Holiday Tradition

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How does your family gather for the holidays? In the past, mine would always gather at one person's house. The host family would have to do all of the cleaning beforehand and figure out where everyone would sleep. Then we’d all crowd in and, essentially, take over their home for a couple of days. If everyone was able to make it, we’re talking 30+ people in all! While we always enjoyed our time together, a few years ago, we decided to start a new tradition…large family vacations (this might have been my idea)!

Why Plan A Large Family Vacation?

First of all, you get to go somewhere new! It’s a fun adventure that you can all enjoy together. Second, there are some great places to stay where you can all be under one roof, have plenty of room, and no one has to spend their precious time & energy preparing for company. And third, it’s a great excuse for a little vacation!

Our last trip to the beach was awesome! It wasn’t too cold and the kids even played in the water & the sand a bit. We took a jog on the beach (between all the eating) and some went in to explore the town nearby. We talked, played games and had a great time!

How To Plan A Large Family Vacation

There are many places you could go and just as many ways you could go about planning and organizing your trip, but here’s how we do it:

1. Choose a lead organizer

Although everyone should have a say in where you go, one person needs to be in charge of booking the place and generally organizing the trip. In my family, that’s me (no big surprise there). This person may be paying for the house in advance as well…more on that below.

2. Start EARLY

We start planning one year out and we go on our trip over Thanksgiving. So, each year, at Thanksgiving, we talk about where we’d like to go next year. Since large family vacations are fun and tons of families are doing it, depending on how big your group is and where you want to go, houses big enough to fit your group will fill up fast. You need to start planning about 1 year out and book as quickly as you can. We waited just a little too long once and had to split up between two houses. It was okay, but not as fun as all being under one roof.

3. Get a rough number of people

You’ll need a rough idea of how many people will be going to start with. With the trip being a year out, there will be some fluctuations, but most people know if they will be able to take off work or if they are going to their other family for Thanksgiving next year. Get everyone to tell you yes or no with as much certainty as they can.

4. Choose your dates

We like to stay 3 nights – that seems like the perfect amount of time for us. We all get to be together for several days, but not so many that we are ready to kill each other.

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5. Choose a location

This can start with a group discussion, of course. We all live in Texas (all over the state) so we try to choose places that are within driving distance for all and we try to mix it up so we go somewhere different each time. We’ve all headed north to Broken Bow, Oklahoma and we’ve headed south to Crystal Beach, Texas.

Some will have to travel farther than others, of course, but we try to mix it up. If your family is more spread out, you’ll have to consider who may need to fly to get there.

You’ll also want to consider what everyone wants to do while you are there. We like places that have some stores & restaurants nearby, plus something to do in nature (hiking, beach, etc.).

If you are thinking about Broken Bow, check out our top recommendations for 5-bedroom cabins here.

6. Set a rough budget

Each family unit will pay an equal share. My husband and I, plus our kiddo, count as one family unit. My parents are another family unit, and so on. It’s important to make sure everyone that wants to go can afford the house you are looking at. So do a few searches and discuss it so everyone knows what they’re in for.

Keep in mind the numbers WILL fluctuate a bit as the year goes on, so it’s important that everyone understands that the “per family unit cost” may go up a bit if less people end up being able to come.

Also, in our family, Grandma (aka Ma – the one who started this bunch) doesn’t pay. She tries, but we don’t let her. It’s just a nice little gift we all like to give her.

7. Start a Facebook group message

Assuming everyone is on Facebook, we have found the easiest way to communicate about everything is through Messenger on a big group message.

8. Find a house & book it

I love looking on VRBO to find the perfect house, cabin, etc. There are so many options and you can read the reviews of people that have stayed before to make sure you know what to expect. Plus, VRBO has a ton of houses perfect for large groups. As soon as you find what you are looking for, book it! Typically, these houses will require a deposit when you book and the rest will be due at some later date. Take a look at my top recommendations for luxury cabins in Broken Bow, OK.

9. Show me the money

To make it easier for everyone, I pay the deposit when I book the house. Just before the final payment is due (often 2 months before the trip), I do a final check (via Facebook Messenger) to see who’s in and who’s out. If you’re in at that point, you pay your portion. It’s so easy now with options like Venmo, PayPal, etc.

At this point, our rule is if you say you’re in now, you don’t get your money back if you can’t come for some reason. It may sound a little harsh, but without this rule, the amount per family unit could continue to fluctuate right up until you arrive, and shifting money back and forth would become a nightmare. You are free to do it another way in your family, of course.

10. Assign beds

This step is optional. You can just say “first come, first served” if you’d like. But, in our family, we have all kinds of sleeping considerations and this part can be a little tricky. Plus, many houses that fit a big group will have several rooms with bunk beds. If it isn’t clear in the description of the house exactly how the beds are arranged, you can always message them and ask. Some things to keep in mind:

• Families with babies and little kids may be up in the middle of the night and may need naps during the day. Give them their own room if at all possible.
• Some people snore…BAD (you know who you are…Dad). Give the super snorers their own space or pair them up so the non-snorer families don’t have to suffer.
• Some people use white noise machines or sleep fans. My personal favorite is this sleep fan app – LOVE IT! Again, try to pair them up if possible. If some families are used to sleeping in total silence, the noise will drive them crazy. Likewise, if I had to sleep in a quiet room, I wouldn’t sleep a wink.
• We like to give Grandma a room downstairs with her own bathroom when possible – and we certainly aren’t going to put her on the top bunk.

I choose the bed assignments and tell everyone via Facebook Messenger. Obviously, we are all adults here, so if anyone chooses to trade off, that’s up to them.

11. Create a Sign Up Genius for food

Sign Up Genius is an easy to use website where you can create a list of things you need/want and everyone can sign up for specific items. We have found that this works great for food. We have one family unit sign up for each specific meal (except the Thanksgiving meal).

So, my husband and I might sign up for Breakfast on Friday and we would cook breakfast for the whole big group. For the Thanksgiving meal, we all sign up for individual items: turkey, mashed potatoes, paper plates, napkins, etc. (ok, my family actually makes Mexican food for Thanksgiving, but you get the idea).

Again, this is totally optional and there are many ways you can go about it, but we like it and it helps ensure that you don’t end up with four dishes of green bean casserole.

12. Make sure you know what is not provided

Most houses will have everything you need, but not all. You really want to read the fine print and make sure you know what is and is not provided. The last house we stayed at did not provide towels or paper products so we were all responsible for bringing our own towels, paper towels, toilet paper, etc. This is another reason to choose a location close to stores…just in case.

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13. Have a great time together

We have fun just hanging out, eating, watching football, playing games, eating, exploring the area, and eating some more.

14. Know what to do to clean up

You will have a few responsibilities to take care of before you leave, so make sure everyone knows what needs to be done.

All dishes usually have to be washed, trash taken out & they will often have you take the sheets off the beds and put them in a pile in a specified location. Other than that, you just want to leave the place like you found it. Remember, the homeowners will rate you after your visit just like you rate them.

The only thing left to do is to start planning your next large family vacation! For families that enjoy getting together AND getting out and seeing new places, a mini-vacation can be the perfect way to enjoy the holidays!

Planning a large family vacation can be a bit of work, but it is SO worth it! Visit somewhere new or pick a place everyone loves and return year after year. We have really enjoyed our time together in fun new places and I’m sure you will too.

I LOVE to hear from you – leave a comment and let me know some of your traveling traditions!

If you liked this article…check out these:

• Top 10 Family Friendly Cabins In Broken Bow, OK
• Things To Do With Kids In Broken Bow
• Top 10 Family Friendly Vacation Homes in Dallas
• The BEST Family Friendly Vacation Rentals in Kauai, Hawaii

Until next time…

Until next time…

About The Author

My mission is to inspire and empower families to prioritize travel now, creating unforgettable memories and deeper connections with their loved ones.

I provide guidance and practical solutions to help busy parents integrate travel into their lives, fostering joy, fulfillment, and stress-free adventures. Don’t wait until it’s too late; the time to travel is now.
Learn more about me & My Travel Obsession here.

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