Parents

We Survived Four Generations in One Vacation Home—These Tricks Made All the Difference

A multigenerational family trip in Key West that actually worked, thanks to smart planning (and the right rental).

By Annabelle Canela | Released Aug 14, 2025

My family is anything but perfect. In fact, I'd go as far as to say that we're a group of disconnected connected individuals. Everyone has their own way of living, and some of us even speak different languages. That's probably true of most multigenerational families, especially those with members born in different parts of the world.

I'm first-generation American, which means my parents, grandparents, and some extended family members all came from different parts of the world. Naturally, we all have different ideas of what's "normal."

Still, we just got back from a family reunion, and despite our numerous differences, we all had a wonderful time. And yes, being together is the greatest joy of all, blah blah, but, truly, the planning made a huge difference.

Without sounding too braggadocios, I nailed planning for our family reunion with multiple personalities, generations, and needs. And if you're planning something similar for your large and questionably amendable family, here's how you can survive it, too.

Planning for a Multigenerational Family Reunion

Planning can be the most dreaded part of a big trip, especially when everyone has different wants and needs. My family ranges widely in age, so we needed to make sure everyone felt comfortable in where they were staying, what was available to them, and what we were eating.

Here's the step-by-step process we took to plan a stress-free trip.

Pick a location that works for everyone

Choosing the right spot for your reunion is crucial. You want a location that offers activities for the whole family and isn't too far from where everyone is traveling.

For our family, that meant booking an Airbnb in Key West, Florida, called Lunara Bay Homes. The special part about this Airbnb is that the same company owns all the homes in a private, gated community, so it feels both safe and connected. And if your family is on the larger side—or just needs some separation—each household can rent out its own home while still being only a few minutes apart.

It also doesn't hurt that the homes are stunning. Each property features modern kitchen fixtures, a private pool, a fire pit, and plenty of space to gather.