Winter break is on the horizon. With two school-free weeks at year-end, this is an ideal time for family getaways.

VRBO, Airbnb, HomeAway; you name it, vacation rentals are getting increasingly popular.

They, of course, come with a host of benefits that hotel stays don’t typically offer. Namely, multiple families can now pool together to rent large homes in great locations, spending quality time together with the comforts of a home.

These vacations don’t come without complications, and take a bit of organization and planning to pull off (I won’t say without hiccups because those are inevitable).

After nearly a decade of spending winter break on group trips at our favorite coastal getaway, I’ve come up with a list of travel tips for multi-family vacation rentals.

General Logistics

Who to Invite

Multi-family vacations are born from a variety of fellowships, including extended family or friend groups.

To start, and this is trickier with family than friends, if you’re going to be spending and extended amount of time with people in close quarters, you should feel confident you and your cohorts are very compatible.

As a general rule of thumb, try and make sure everyone has a peer in the group to bond with, including kids. If there’s a kiddo outside the general age or gender group of the others, having them bring along a friend can be a good idea.


Letting all parties have a say in the vacation rental selection will help ensure everyone is comfortable with pricing.

Another option is for the trip planner to pick a spot, then send out details to friends or families to see if they’d like to join in on the trip. In this case the organizer is taking on the burden of the planning, so they get more of a say in the arrangements.

NQM’s No Fail Steps to Finding Your Perfect Airbnb offers fantastic tips! Either way, pricing and payment methods should be laid out explicitly in advance to safeguard that everyone is comfortable with the budget and not surprised by final costs.

Discuss a General Parenting Plan

If there will be children on the trip, it’s a good idea for parents to hash out details of screen time, bed times, snacking and such to make sure everyone is generally on the same page.

Keep in mind that vacations are typically a time when parents loosen up the rules on the day-to-day routines and expectations.

It’s also nice to have a heads up on any kid-related issues that might arise (sibling fights, potty talk, dietary issues) and how best to handle them.


Eat Out or Order-In the First Night

Eating out or ordering in the first evening allows everyone to unpack and settle in without the added stress of having to throw a meal together.

Have a spot picked out in advance so the restaurant is prepared for a large group order.

Assign Group Meals

Have each family sign up for a breakfast or dinner to cook for the whole group.

If there are more adults or couples than meals, multiple families can tackle a meal together. This way guests are only responsible for a handful of meals over the trip, which helps keep the planning, cooking, and grocery list manageable. Everyone should be on their own for lunch so the crew isn’t hopping from one big group meal to the next.

Split-up Staples

It also helps to have a sign-up list for staples such as milk, sparkling water, butter, olive oil, coffee, etc.

Other than assigned meals, guests should also be on the hook for their own snacks.

The Last Dinner and Breakfast should be a Feast of Leftovers

The last couple of meals can be a raid of the fridge.

This helps reduce food waste and eliminate having to pack up a bunch of food to take home.

We’ve had many a “warm-it-up-and-throw-a-fried-egg-on-it” meal over the years, and no one’s ever complained.

Pick out a Grocery Store Ahead

It always helps to have a grocery store picked out near your location to do your shopping. 

This eases some of the packing burden, can serves as a nice break on a road trip, and lets you check out some local flavor.


Let Everyone have a Say

Early in the planning stages, everyone in the group should be polled to see what they’d most like to do and plans can be made accordingly.

Don’t expect everyone to want to do all the same things as you and your family. It’s fine to break off into groups for activities, or for individuals or families to head out on their own.

Plan Ahead

Have a rough idea of what activities you plan to do ahead of time so everyone can make the most of their time away.

Reservations can be made ahead of time as needed, and hours of operation can be confirmed in advance.

Plan Two Activities a Day

I recommend planning one outing after breakfast and another after lunch.

On our annual beach trip, we do mid-morning beach hike, then hit the indoor pool or tennis courts late afternoon (stopping of course at the candy shop on the way back).

After dinner everyone kicks-pack for an evening of leisure with games, movies, and socializing.

Pick a Rental with Fun Amenities

Selecting a vacation rental with a game room, swimming pool and/or hot tub, bikes and other fun perks is a huge bonus when on a group trip.

It means less packing and less planning, as fun is “built-in” to the setting.

Again, read through the filtering tips that helped Elizabeth find Zayly Lodge in NQM Finding Your Perfect Airbnb.

Bring Along New Games and Puzzles

Group vacations are a great time to open up new games and puzzles.

Games are extra fun with large groups, and being on vacation allows for the time to pick up on something new (we are planning to bring this one on our upcoming beach trip).

Puzzles are also an irresistible form of entertainment. Simply set one out on a large open table and passersby will be sure to join in.

Build-in Alone Time

As much as I love group trips, I’m an introvert and have to build-in alone time each day, otherwise I quickly feel worn out.

I try to start the day with a run or long walk to get in the right headspace for a day of socializing. We often use the lunch hour to go out on our own as a family, and then sneak in a little solo time before bed to read and regroup in our room.

I find it helps ward-off meltdowns when kids are encouraged to have some quiet time each day to recalibrate. Kids need solo downtime too.

Clock in Kid-Free Time

Vacationing with young kids can feel like every other day for parents, just in a different location.

So, it’s important for both parents to get some kid-free time.

My sister takes a week-long, multi-family trip each summer where they build in a wine tasting day for the ladies, and a golfing day for the guys.

You can also swap parenting duties with other couples so everyone gets a date in the mix.

Bonus for all if you can fit in a girl’s/guy’s outing, plus a date with your partner.

Sleeping Arrangements

Assign Rooms Ahead

Prior to arriving, or possibly even booking, all parties should get to see photos of the available rooms and state their preferences

Is there a family with little ones who are still napping? They will probably favor the most remote choice. Early risers; give them the room closest to the kitchen so they can bang away at the coffee pot without disturbing others.

If one couple ends up with a smaller or less desirable room, the rest of the group should find a way to even things out by paying more, taking on extra meals, or buying dinner out.  Just make sure everyone is on board with the plan so there are no surprises or hard feelings.

The Family that Books Gets the Best Room

Generally speaking, the family that handles the booking, which is often no small feat, should get the nicest room.

If this is you, take into consideration other’s needs of course, but don’t feel bad grabbing that balcony room with a view. If someone else in the group has handled the booking, you should insist that they take top pick.

Now it’s time to go have some adventures, and of course fun! Your trip will never be perfect, but it will always be memorable.

Also read:

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Feature photo by Adobe, ©Happy Mom Life Lab. Article images licensed through Sarah Lukas (first multi-family photo, lodge bedroom, child with a laptop), Adobe (kids standup paddling, other multi-family photo), and Inese Westcott & T. Kao (outdoor hot tub), all in the context of this article are ©Happy Mom Life Lab.

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two families enjoying vacation together

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