Getting the Whole Group Together for National Vacation Rental Month with Wyndham Vacation Rentals


Six tips for vacationing (happily!) with multi-generational, extended family groups. Great ideas for fun family travel from Boxy Colonial blog

Hey, guess what?! July is National Vacation Rental Month, and Wyndham Vacation Rentals is having a month long celebration; find out how to enter to win your own road trip getaway at the bottom of this post.  I had no idea this was a thing until recently, but it makes a lot of sense, because July is when everyone’s out of school and going on vacation. If I were to declare a month National Vacation Rental Month, I would pick July, too. Unless I just wanted to mess with people; then I’d pick something random like March.

So I’m here today to sing the praises of vacation rentals, particularly for big extended family vacations, and to share some tips for Ways to Get the Whole Group Together. This is all very timely, because we just got back last week from a trip to Santa Cruz,CA with Dave’s parents and his sister and her family, and we all stayed together in a big rental house. This was our first trip to Santa Cruz together, but we’ve rented houses as a group two other times; once on the coast of Texas when Gus and his cousin Benjamin were super tiny (the first time they met!) and then again a few summers ago on Cape Cod. Until a few years ago, Dave’s parents owned a house on the Cape, so we have lots of experience staying together in that house, too.

I nearly always prefer rental houses to hotels, even when it’s just my not-so-little nuclear family. Shoving six people into a hotel room is no fun. And, of course, we don’t all fit into most standard hotel rooms, so we end up either getting two rooms or getting a suite, which often pushes the price of a hotel stay above that of a rental house. And with a vacation rental you often/usually get a full kitchen, multiple bedrooms with plenty of beds for everyone, and a separate living room. Sometimes you get bonus features like pet friendliness (I know some hotels are pet friendly, too, but I never feel comfortable leaving my current crop of dogs in a hotel room, lest they start yapping every time someone walks down the hall) or a great (outdoor or indoor) space for the kids to play in, too. And if you go with Wyndham Vacation Rentals, you can get all of that plus, at many of their properties, anything you might miss about a hotel stay, like shuttle service, a concierge desk, and housekeeping.

But with a big group, the advantages get even bigger. I’ve been trying to put my finger on exactly why, and I think the main thing is that a rental house, paradoxically, both brings your group together more AND gives you more privacy and space than staying in a hotel. Last year, for our big DC trip with the same extended family group, we weren’t able to find a vacation rental that worked for us (mostly, I think, because we waited too long to start looking). We ended up in three 2 room hotel suites, which sounds like a lot of space, but was, in reality, kind of cramped. There was nowhere for the kids to hang out together without being right on top of grown ups. Each suite had two rooms, but just a hallway connecting them and no door, so there was still the whole tiptoeing around trying not to wake up kids at night. So we were all right on top of our kids (even the grandparents, who ended up sharing their suite with Milo and Gus) and yet really spending time together as a group required leaving the hotel all together, since there wasn’t space for everyone in any of the rooms.

Santa Cruz rental house

For this year’s California trip, on the other hand, we had a huge house with tons of room both for spreading out and for hanging out together as a group. It had six bedrooms (Milo, Gus, and their cousins, Benjamin and Louis all shared a room with 2 sets of bunkbeds, but everyone who wanted their own room got to have one), plus two living rooms and two kitchens! It also had a game room in the basement with foosball and ping pong and video games. So everyone could have as much or as little togetherness as wanted/needed. The kids looked like this a lot when we were at the house:


While they were doing that, we could go hang out in the other living room:


We called the kitchen we kept the beer in the Fun Kitchen:


But we did most of our cooking in the other kitchen, because it had a fancy stove:


But really the best feature was that this was about six houses down the street:


twin lakes beach Santa Cruz

So now that I’ve laid out why I think vacation rentals are the way to go for big family vacations, here are a few tips for how to get the group together and keep everyone relatively happy while you’re on vacation, gleaned from many a group trip over the years:

1. Pick a destination that works well for everyone: We had a great trip to DC last year, but I’m not sure it was really the perfect pick for such a big, multi-generational group, in retrospect. There was a lot of walking and a lot of museums and a lot of taking turns keeping one year old Abe out of trouble. Secret confession: the beach is not usually my first choice for vacationing. I like the beach, but I don’t LOVE the beach the way a lot of people do. But the beach is a great place for a big, mixed age group. Kids (and adults) can play in the waves and dig in the sand. People can go for walks along the beach or just sit and look out at the ocean. Other kinds of trips would work well, too; just give some thought to who you have in your group and what their common interests are.

2. Choose the right rental house: I touched on most of this up above, but make sure you spend some time talking about what everyone wants and needs in a vacation rental. Do some kids have to have their own beds if you want them to fall asleep? Is a nice, well equipped kitchen really important, or will you be eating out most of the time? What are the group’s priorities for location (do you want to be able to walk to restaurants and shopping? Is outside space important to you?) We tend to spend a lot of time looking at houses and e-mailing back and forth in the months before the trip. It can be overwhelming, but it’s also a good way to get excited about the trip.

3. Find activities that everyone can enjoy: do some research online and find attractions at your destination of choice that will work well for everyone in your group. As I mentioned, the endless museums in DC last year were not the best for Abe (and some museums that the adults might have loved we skipped because they wouldn’t appeal to the younger kids), but we did find other things, like the zoo, that everyone could enjoy. Reviews on TripAdvisor and the like can give you an idea of what to expect from a particular spot. Is there too much walking for some people in your group? Are the kids in your group old enough to appreciate it? Do kids love it, but it makes adults miserable? Several of the kids were really interested in checking out The Mystery Spot in Santa Cruz, but most of the adults wanted to skip it and I read some reviews that said it would be too much standing still and listening to someone talk for the younger kids, so it didn’t make the cut this trip.

4. Don’t feel like you have to spend every moment together: I think this might be the trickiest thing about traveling with a big group: finding the balance between togetherness and time on your own. Especially when you’re with extended family that you don’t get to see often, you can feel like you’ve come all this way just to spend time with them, so you need to pack in as much together time as humanly possible. But that can backfire in a big way if you overdo it and all wind up sick of each other by the end of the trip. A vacation rental where everyone can retreat to their own space helps with this, of course. As does taking some time to do things in separate, smaller groups some days. Those places you decided weren’t great for the whole group in number 3 up there? Maybe just a couple of people can take off and do them one day. Dave and I stayed behind with Abe while the rest of our group went on a whale watch because a two year old on a boat for four hours sounded….terrible. Nana and Grandpa stayed behind and enjoyed a quiet house sometimes while the rest of us did more kid focused things. We didn’t get around to it this trip, but in the past the grandparents have offered to keep the grandkids one evening while all the parents to young kids get to go out for dinner. I feel like this group has traveled together enough that we’re pretty good at working out the dynamics, but any time we travel with a different group, it takes some time to sort out the right balance. It’s good to have actual conversations about it so everyone’s on the same page.

5. Meals are a great time to reconnect with everyone: Everyone has to eat! So on days when people go their separate ways for whatever reason, it’s nice to have an evening meal at a restaurant or back at the house so that everyone will have a chance to be together and talk:


6. Don’t overplan/keep it flexible: My natural tendency is to plan so many fun things! for every day of vacation. But this type of planning doesn’t work so well with a big group. It can be maddening to have too many commitments and constantly be worrying about getting everyone out the door on time. We had a couple of definite plans going into the week (the whale watch had to be booked in advance, for example), but most of the days were up in the air. It helps to pick a destination that lends itself to this kind of spontaneity. As my sister-in-law pointed out before the trip started, “the beach is always there.”

I’ll be back later in the week with more details about what we did in Santa Cruz and more pictures of the beach to make me nostalgic for two weeks ago….

To plan your own vacation rental experience, visit

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I was selected for this opportunity as a member of Clever Girls and the content and opinions expressed here are all my own.


Getting the Whole Group Together for National Vacation Rental Month with Wyndham Vacation Rentals — 4 Comments

  1. LOVE this!! Vacation rentals are the way to go. We rented a condo in Montana when we went skiing. It was so great to have an area to hang out together. Plus we could put the kids down and still hang out with everyone. Of course having the kitchen was great because you get sick of eating out and waiting for tables for large groups. Alright you’ve totally convinced me. I’m booking another vacation now!

    • There you go! Vacation every month! I forgot to even mention the whole not wanting to eat out every time with babies and toddlers thing!

  2. We have never done a vacation rental before, but are planning to go this route for a trip to San Diego in November. My parents will be there and this just makes more sense for all of us. Thanks for the tips. (I also tend to be an over planning cruise director type. Sometimes, downtime is necessary>)

    • That’s what they say about downtime. I’m sort of bad at downtime on vacation. I like to have downtime at home instead ;).

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