Vrbo 2026 Vacation Rentals of the Year spotlight

[00:01:14] Tim Rosolio Out of two million properties, you were one of the ones that we picked. Not just because this is a beautiful home, but also you are a great hospitality provider, which is really great. But let's first start talking about this place. I mean, you have 270 degrees of panoramic views of the lake. And at the same time, the house is really modern. I think in the reviews it said that it was a modern marvel. I saw that a lot. So, tell me a little bit about just like, what was the vision when you were putting this place together? 

[00:01:49] David Rose I've loved mid-century modern as a design style. I love how there's so much glass, and the glass runs all the way up to the roof. And we've done that here. We put a butterfly roof on, so it creates all these really interesting angles where the glass just comes up and intersects with the roof, and it just affords beautiful, as you said, visibility into the woods, into the lake. One of the reasons why we were able to be so close to the lake, you almost feel like you're touching the edge of the lake with this deck that's out here. And that's because we had an old house when we bought the place, and that we could use the existing footprint. So, the very same foundation that was used for that is used for this house. And so we're able to be right up to the edge of the lake, and people just marvel at the views from the first-floor level, this floor level, the upstairs level with lots of perches. We have kind of a place to go out and read a book and do a call up there. There's like a place to read and kind of overhear conversations here. There's plenty of space on the hearth if you want to hang out and look out towards the lake. There's like a hammock place, there's a fire pit place, there's a hot tub place, like all of these places, most houses have magnets like a kitchen island that brings people together. This is a house that does that, but then also serves to have these nodes that pull people into, if they want to, spending time on their own to read, to write, contemplation, kind of whatever you want to do.  

[00:03:19] Tim Rosolio It's the perfect place to get away with this amazing home, but also like the lake is still the star to a certain extent. I was, you know, but while we were preparing for this, I was upstairs on a conference call earlier. At one moment, I kind of looked outside, and I saw the view, and I kind of went like, ah, that's enjoyable.   

[00:03:40] David Rose Yeah. It really is so peaceful and calming, isn't it?  

[00:03:42] Tim Rosolio Yeah, it's a special place. It really is. So, you mentioned the old house. 

[00:03:48] David Rose Yeah, we bought the place in 2000. I'm a tech entrepreneur and had just sold a company and kind of had the resources to do it at the time. When I was a kid, I grew up in Madison, Wisconsin, and we would always go up to the northern woods of Wisconsin. And my dad's a physician. We never got to see him very much except for those two weeks in the summer where we could kind of do family camp up in northern Wisconsin. And it was just so much fun to go swimming and water skiing and canoeing and fishing together. And, like, I just treasured those moments with him as something that I wanted to re-create for my own family and my own kids.  

[00:04:24] Tim Rosolio Yeah, and I really like how you're touching on that, too, because you know, Vrbo as a brand, we're really about families and groups getting together. And a big part of it is just making sure that people have time to spend together and get away. I think, you know our clientele, especially in today's society, we're busier than ever, but it's really incredible when a family or group can really enjoy each other's company in a way that's getting away. It's a really special opportunity.  

[00:04:53] David Rose I love when this place is used for multi-generational gatherings. We have repeat customers that will come back again year after year, and people will fly in from all over the world just to congregate on the most beautiful lake in the country in my opinion. There's a downstairs bedroom, so if somebody doesn't climb stairs, they're fine in the downstairs bedroom. There's two rooms that are packed with bunk beds, and little cousins love to be together and with each other. My goal always is to tire everyone out so much with all the activities like camp. I think of this as like it's family camp, except the food is so much better than camp. But there's so many activities that by the end of the day after they've been doing archery and swinging on the swing and doing a zip line and swimming and kayaking and going to watch the loons over in the loon cove, and go to the eagle's nest. By the end of the day, they're so tired out. That even though there's four of them in a room in bunks, still they're zonked.  

[00:05:57] Tim Rosolio Yeah, it sounds like a great camp. Now, what percentage of your guests would you say make s'mores while they're here? Oh. And do you supply marshmallows?  

[00:06:07] David Rose We do. Yeah. I mean, there's an indoor fireplace, which you see here, which is, which is lovely year round. There's also an outdoor fire pit, and with like some big giant logs that are around that. So, people can really hang out and make a fire in the evenings. And I think, I think everybody does some s'mores. Yeah. They're a crowd favorite.  

[00:06:24] Tim Rosolio Yeah, I feel like I have to.  

[00:06:25] David Rose Right. I mean.  

[00:06:27] Tim Rosolio Which is actually really interesting because when we were initially looking at different hosts to do this, we looked at your background. We saw MIT lecturer, a futurist of sorts. You've invented a few technological things. When I get here, the interesting thing is I don't feel like I'm on the Jetsons. There's no refrigerator that's talking to me. I wouldn't consider this a smart home. Are there any ways that perhaps you've been able to integrate technology while at the same time making it feel like camp? 

[00:06:59] David Rose Yeah, my vision of future of technology is that it disappears into the fabric of everything around us and is unobtrusive. And I've tried to do that as much as possible here. So, there is a lot of technology. Like, glass is a technology. The steel that this house was built with allows you to do a nice cantilevered front. There's up on the catwalks. There's stainless steel, which gives you this nice precarious way of looking through and looking down on the action in the living room. The floors are all heated from the basement floor. Every floor has radiant heats, and so it feels nice on your toes. But none of those are things that you'd ever notice. They're not a new interface that you're confused by.  

[00:07:44] Tim Rosolio Yeah, it's not an obvious technology. It's not in your face.  

[00:07:47] David Rose When people are on vacation, you want to get away from all the interfaces and screens of your life. And so this is a place for respite and recovery and being away from the burdens of that kind of complicated, inscrutable technology.  

[00:08:02] Tim Rosolio But you know what technology I noticed you do have? Talk about some of the stuff you have downstairs. I mean, it seems like you bring your luggage, and in terms of activities here, you're set up. Like you have 

[00:08:14] David Rose Oh, yeah.  

[00:08:14] Tim Rosolio Thought of everything.  

[00:08:14] David Rose I mean, I think the design of a place changes what you do and how you feel about yourself and connection to others. And certainly, the availability of activities and the tools for activities mean that people go and play on the lake. So, we have snowshoes, we have crampons for people who want to go hiking on the ice. There's skating, there's cross-country skis available. There are bows and arrows. People put the archery target out in the yard. Everybody wants to do that.  

[00:08:46] Tim Rosolio Yeah. Right. But we talked about our liability insurance solution.  

[00:08:51] David Rose But in the summer, you've got like stand-up paddle boards and kayaks and canoes and a sailboat and a rowing scull, which a lot of people try and tip over, which is always a fun adventure. But I mean, I think of these as like, they're activities that are a little bit venturesome, but, like, they're kind of, you can fail without a lot of downside in safety, right?  

[00:09:15] Tim Rosolio Yeah. Yeah. I mean, a family can come here. Maybe they're not from this area of the country. Maybe they've never done these sorts of activities before. And relatively quickly, somebody can be up and running with a lot of these activities.  

[00:09:29] David Rose Exactly. Exactly. And they have so much more fun, too. And, I mean, I have friends that come up here and I'll say, like, "What do you want to do today?” And they'll say, "Everything, like, let's do everything in one day. Let's try to pack it all in.” And then I have other friends, one of my partner's friends, I'm thinking of, and she said, “David, I'm not doing any activities. I'm sitting in the hammock, and I'm reading a book. You can't get me to do it.”  

[00:09:48] Tim Rosolio It's a good place to do that.  

[00:09:50] Tim Rosolio Is it time for hosts to get rewarded? For a limited time, hosts can earn OneKeyCash travel rewards for listing an eligible vacation rental on Vrbo. OneKeyCash is a flexible rewards currency you can use to book your next trip on Vrbo, Expedia, or Hotels.com. Visit vrbo.com/podcastoffer to learn more. Terms and conditions apply. 

[00:10:13] Tim Rosolio So, let's talk design. This is a very intentional design, clearly. What was the inspiration for this? Because when you walk in, you say what?

[00:10:22] David Rose Well, I think I always wanted to be an architect. I was a physics major and also a fine arts major undergrad. And the combination of those is design and architecture. And I worked with a super talented architect, Tom Murdough, for a few years on the design of the house. Certainly, there was a lot of Japanese design, Japanese elements. When you come in, there's this notion in Japanese architecture of progressive disclosure, which is you don't kind of reveal everything, all the structure of the landscape and the house initially, but there's a path in that hides some things. There's some tailored views of the lake. You don't really get a sense of exactly what the site is until you come into the entrance. Frank Lloyd Wright had this idea of compression and expansion, where you keep the ceiling low when people walk in. And then boom, like you come in to this room and you kind of see the expanse of glass, and that's more impressive because of the compression that you had in the entryway.

[00:11:27] Tim Rosolio Yeah, it's funny he mentioned that because I've actually noticed some of the ceilings are literally slanted, I guess, to create that effect. So, let's also then just talk about like the hospitality experience. We know communication's important. We know having all the right little things is important. What are some of the things that you do to deliver hospitality beyond the home?

[00:11:51] David Rose Well, I think the communication before people arrive to kind of set expectations and to make sure that they know where they're going. Once people arrive, I really enjoy that first conversation to kind of tell people where the hot tub is and to make sure and turn up the heat because it takes a few hours to get to full 101 degrees. I really enjoyed that conversation because I'm able to share some of the things I love, especially for the season. There's different hikes I would pick, based on the temperature or based on whether there's snow and different activities. And it's nice to be able to give people that advice and also just learn about them. Like, do they have a big group? Are they super active? Are they into hockey? Are they into fishing? And then I can kind of tailor advice based on what they're into.

[00:12:35] Tim Rosolio Yeah. You can make it pretty personalized. And, you know, what I found with my vacation rental is when you do that check-in after somebody arrives, you're getting that opportunity to fix if there's anything wrong in a relatively non-intrusive way. And Typically, there's nothing wrong, but maybe it's sometimes just something like what's the Wi-Fi password? And you can say, oh, you are getting the opportunity to demonstrate the value. Now, I also noticed, though, in terms of hospitality, you have all of the little somethings in the house. So, we're eating lunch here beforehand and somebody brought in a cold ham sandwich.

[00:13:17] David Rose Right, that would be so much better toasted.

[00:13:19] Tim Rosolio This guy brings out a panini maker and he's like, “I got this.” And it just came to mind that you probably have all of the small things that make the trip that much more convenient and effortless.

[00:13:33] David Rose I will have a friend who's really into cooking, and they will recommend a panini press or a different coffee. We have all three ways of making coffee. We just got some new different grill thermometers. So why not? Why not give people all the tools to be able to make the best food experience that they want to make or something else that can be tailored to them?

[00:13:57] Tim Rosolio You've clearly over time developed a playbook, and there's all these things that you've learned. Were there any key learnings as you were getting up the learning curve of being a host? Like, what are some things that maybe you didn't realize was gonna be challenging but didn't end up being a challenge?

[00:14:14] David Rose Yeah, I think it helps to be a Vrbo customer myself, and to take our kids on vacations at various times in their lives, and understand what's valuable in California.Or somebody has a pool and you don't really know where the toys are. It helps to have had those experiences and be able to bring those to this place. And one of the things we've done differently over the years is, you know, better lighting when people arrive so that they can just wayfinding is easy. We put little messages all around the space, like no one's gonna read the big book on exactly how to use everything, but when it comes time to figure out where the grill light is or how to open the lift-and-slide doors or using the Apple TV in the basement or something, like you just kind of want to put a little tailored note just for that moment, just to be able to solve that problem in that moment.

[00:15:08] Tim Rosolio Yeah, that's a really cool trick. I need to do that. You know, I also thought it was interesting how you were talking about being a vacation rental traveler, too, and going around the country. One thing that we found many good hosts or property managers do is they make sure that there's something very specific and local about the experience. There's a partner of ours, Ben and Tiffany Edwards. They have these amazing properties in Monterey, and their welcome gift is this great cheese and these California wines when you walk in. And when you walked in there, you say, wow, I'm certainly in California.

[00:15:43] David Rose Who doesn't love that? Right.

[00:15:45] Tim Rosolio Don't sounds terrible. Yeah, right.

[00:15:48] David Rose So for us, like cider or there's a great, there's a great creamery that does ice cream that's up, right up in Sandwich and having ice cream, and maybe some dairy-free option, like in the freezer is something that you wouldn't expect. I think the cheese plate and the wine is, is something that has become more expected in Vrbo. I am very interested in getting into kind of other elevated experiences, probably not hot air balloon yet, but.

[00:16:15] Tim Rosolio We did talk about liability insurance.

[00:16:17] David Rose But what are other things that would just take it up a level? Could we have a naturalist who will take you on a hike? You know, could we have somebody who comes by and takes the kids tubing? You know, could we have a chef that comes by and shows you how to make something that's local? You know, I would like to be on more vacations where those things are available.

[00:16:38] Tim Rosolio Yeah, I think it's a great idea. And, you know, Vrbo certainly is investigating ways that we can leverage the depth and breadth of Expedia Group to try to plug in, for example, activities and experiences. And I think that's something that we will look at in the future, as well as potentially, you know, stuff like flights, which wouldn't necessarily be something local, but it's a way that we can really think about more of an end-to-end trip rather than just running a lake house. So, I think it's probably a great thing for that for us to partner on. And the cool thing is, you know, we can talk to great hosts like you, and you can speak to these, the things that people love to do when they come to this area of the country, like I had never been to this area of the country before, but I'm coming back. I'm coming back. So, you already talked a little bit about the intergenerational, the multi-generational stuff. How do you attract those guests? Because we know that that is a special trip.

[00:17:34] David Rose This house is really good at hosting a big group and a big multi-generational group. The experience of having somebody who is in their 80s, who doesn't have a lot of mobility, but can swim, and then having kids that wanna spend all day in the water, and even after dinner, they wanna go out to the raft and have another swim, or you might wanna do the hot tub after all the kids go to bed. That kind of experience is just fantastic and really magical in a place like this.

[00:18:03] Tim Rosolio Yeah, and I noticed downstairs is set up in a way that is sort of perfect for the kids to hang.

[00:18:09] David Rose Yeah, right, right. One of my values in terms of the kind of layout of the space is to try to make the hearth the center of the living room rather than a screen the center of the living room.

[00:18:21] Tim Rosolio And so we have that fireplace.

[00:18:23] David Rose That's true. But putting the entertainment into the basement tends to aggregate the little ones into the basements. And there's not a lot of stuff that they can break down there. They can have ping pong and ping pong ball fights and watch a show and do whatever they want in the basement. And that helps to have more sane conversation after dinner.

[00:18:46] Tim Rosolio Yeah, they're doing their thing and the adults will hang out up here.

[00:18:49] David Rose Yeah, it kind of pulls the cohorts apart in a nice way.

[00:18:53] Tim Rosolio Brilliant, brilliant. Yeah.

[00:18:55] David Rose We love hosting people, but we also love it when people enjoy this place. How could you not want people to have a great experience in a place like this?

[00:19:03] Tim Rosolio Yeah, it's fun to share. It's fun to share what you've put together. Yeah, kind of deserves to be shared in some respects. I think that's a way I would put it, especially at such a unique home. I mean, like my vacation rental is a very old home. And like, honestly, it's the sort of home that would probably be hard for somebody to live in 365 days a year. But for one week, all of the quirkiness of it is actually part of the charm. Now, I wouldn't say this is quirky. This is just really nice. If you want me to live here 365 days, you're counting me in, but there is something special about the unique, the unique home.

[00:19:40] David Rose We love it that when people come back year after year and when people come from far-flung places, and I feel really proud to be selected by Vrbo for the award.

[00:19:50] Tim Rosolio Yeah, it's a special place. You're a special host. Congratulations on Vacation of the Year. But more than anything, I would just say, thank you for your partnership. We get you bookings, but you're the one that delivers the goods and delivers the hospitality, and makes people say that they love vacation rentals, and they love this type of travel. And hopefully they also like Vrbo too. So, thanks for everything that you do.

[00:20:14] David Rose Welcome. I'm really pleased to be a part of it.  

[00:20:18] Tim Rosolio With that, David Rose.  

[00:20:20] David Rose Thank you, Tim. Great to have you here.  

[00:20:23] Tim Rosolio Thanks again to David Rose for hosting us for this episode of Powering Travel at this beautiful house, Lakefront Escape on Squam. And for sharing how he makes a magical experience for his guests from design to hospitality. To see a full list of all of Vrbo's vacation rentals of the year, including Lakefront Escape, visit the link in the description, and stay tuned for the next episode of Powering Travel by following us on Spotify, YouTube, Apple Podcasts, and anywhere where you listen and watch your favorite podcasts. Thanks again for listening to Powering Travel, brought to you by Expedia Group.