The Vacation Rental Key with T and T

Episode #12 - Who's Really Making Vacation Decisions? Teens, Points, and the New Economics of Travel

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The vacation rental landscape shifted dramatically during Summer 2025, revealing crucial insights for managers navigating this new terrain. Tim Cafferty and Tiffany Edwards unpack five game-changing trends that defined the season and will likely shape the industry moving forward.

Booking windows have contracted at an unprecedented rate, with a remarkable 42% of July bookings classified as last-minute reservations. This shift isn't subtle—some properties saw booking windows shrink by 6-8 days compared to historical patterns. Revenue management now demands constant vigilance, with successful operators monitoring pricing hourly rather than monthly. Behind this trend lies a perfect storm of economic uncertainty, high credit card debt, and consumers trained to wait for last-minute deals, creating a more calculated approach to vacation planning.

The decision-making process for vacations has undergone a fascinating transformation. Survey data from Walton County, Florida reveals three in five teens now influence vacation planning, while American Express reports 68% of Gen Z and millennial parents involve their children in destination choices. Additionally, specialized group travel—girls' getaways, guys' golf trips, mother-daughter retreats—represents a growing market segment deserving of targeted marketing approaches.

Financial consciousness defines today's traveler. With Americans spending 25% less on vacations according to the Washington Post, guests scrutinize cancellation policies and increasingly leverage reward points to offset costs. Property managers listing through point-based platforms like Marriott Homes & Villas have seen revenue increases of up to 15%, suggesting strategic opportunities in how properties are positioned and marketed.

The podcast also explores the critical importance of pre-season maintenance programs. Properties implementing comprehensive spring inspections—focusing particularly on HVAC systems, sliding doors, and appliances—reported dramatically fewer peak-season emergencies, preserving guest satisfaction and avoiding costly refunds during high-revenue periods.

Whether you're evaluating new tech vendors or reassessing property owner relationships, this summer offered valuable lessons in partnership management. Join Tim and Tiffany as they share practical strategies for adapting to these evolving dynamics and positioning your vacation rental business for success in the seasons ahead.

Speaker 1:

You're listening to the Vacation Rental Key with T&T, the podcast for vacation rental managers by vacation rental managers. I'm Tim Cafferty and I manage two companies, one in Virginia and one in North Carolina. I'm one of the two T's.

Speaker 2:

And I'm the other, T Tiffany Edwards, born and raised in the vacation rental business. I help manage our family businesses from Key West all the way to Kauai.

Speaker 1:

In the next 30 minutes, we're going to give you our keys to success in the vacation rental business.

Speaker 2:

Welcome back guys. Congratulations, tim. We have made it to the end of summer.

Speaker 1:

Oh, okay, what have we made? Well, yeah, the next podcast we drop is going to be on Labor Day. So yeah, I guess we did make it. There were some touch-and-go moments, though, this summer. I'll tell you.

Speaker 2:

Every summer is with its own mix of up and downs, but I think it's really important for us to take a look back of the last couple of months and really think through our highs and our lows and share our key takeaways for the summer of 25.

Speaker 1:

There have been some. I think we did have some highs. It's hard to see them at the moment, but when you sit back and go, yeah, we did pretty well on that and there's some things that caught us by surprise. So now that we're at that point of the year where we are at a moment where we can maybe take a breath, let's look back at some of those keys that we saw this summer. I think we've got about five of them that we want to cover today.

Speaker 2:

I think the first one is going to be of no surprise, and I know that we've mentioned it in our last podcast about overall trends. But, man, this one came this summer aggressively, and that would be the shorter booking windows. Tim, I know that you've experienced that as well.

Speaker 1:

Indeed, I was just looking at our July numbers. As we're now at the point we kind of look at what happened last month, 42% of the bookings we took in July were what we would call last minute bookings. I have never seen anything like that.

Speaker 2:

And even for us. I pulled some information for one of our companies. In July we had a cut of six days for a booking window and then in August we had eight days shortened, which is pretty significant when you look at them coming closer and closer into that time frame.

Speaker 1:

So what do you think is causing this? People just not planning anymore, I think everyone's planning, I think anecdotally.

Speaker 2:

my take is that we're entering into an uncertain economic time, or have been in an uncertain economic time. I think credit card debt is really high. If you don't kind of have your pulse on what credit card debt is, you should go ahead and look at that, because most of your guests are spending or purchasing on their credit card for a reservation and they'll hold out until they've maybe made some of those payments. But with that financial uncertainty, people are taking less trips and we've trained them to wait on a deal. It's like when you go online and you put a bunch of stuff in a cart and you wait for someone to tell you that you look nice and pretty and send you a 20% off discount before you pull the trigger on the cart. And I think that's what our guests are starting to do. They're waiting to see if they've got money in the bank, if they have a little bit of available time and if the prices start to drop.

Speaker 1:

Well, I don't think I've ever had anybody tell me that I bought anything. But okay, I'll go with that. But what it means to me is that we have to be on our game of reviewing those revenue management reports weekly, not monthly, and it has even become daily. Weekly, not monthly, and it has even become daily, and maybe even by the hour sometimes. You cannot ignore that. I can't stress enough. You need to have somebody looking, reviewing and utilizing the tools that you have to make sure that you're positioned properly.

Speaker 2:

I think it's really important. I'm not a revenue management individual. It's not my absolute strength. I love diving into those weekly reports with our team, but there really has to be someone in-house that that is really all that they do. I don't know, Tim, if you follow the same protocol, but we've been very successful on making sure there is one-stop shop within all the companies that monitor that and I will say this summer has been almost on an hourly basis. It's crazy. We've never looked at the revenue management as much as we have in the last three months.

Speaker 1:

Absolutely right. The thing that I can't get my head around really is looking at those reports, looking at the data. It's all trailing information. For the most part, it's telling us what's happened in the market. It's not telling us really what's happening in the market. So you still have to have the experience in that person to go. Well, I know it is August the 9th. At what point do I start panicking about August the 23rd? Because the revenue tells me that the ADR is right and the market is here, but we are here.

Speaker 1:

That whole conundrum really takes some skill. I've mentioned before that we've had some last minute bookings that just made me scratch my head. I think I mentioned in the last podcast that we had somebody book one of my personal houses the Friday before a Sunday check-in and I actually went and visited with that guest. I gave him a little gift and a welcome, so I was really surprised. Yeah, we were just sitting at home and it was Friday night and said you know what? Let's go to the beach. I just can't get my head around that mentality.

Speaker 2:

And Tim, I know that you've referenced this before too, but going back to the idea of someone really knowing your marketplace also needs to understand the holiday sector as well. I know you've made a reference of when the holiday for 4th of July falls on a Thursday or a Friday what that looks like. You also need to look at Easter. This year was in April. Last year was in March. How does that change some of your numbers? You can't just understand what a software is putting out to you. You have to really understand the market and some of the context of historical data.

Speaker 1:

No doubt. And then individually for properties, you need to look as well. We just took on a property in a local boating community and it's the first one we've had in that area. The first thing we looked at is when are the big fishing tournaments? Because we need to make sure we are priced properly for that property for that specific event that's coming up, that we know we're going to book that property. How are we going to get the most dollars for that owner?

Speaker 1:

And those kinds of things don't come to you right away and they're not on an algorithm somewhere that you look at. You've got to have that experience to balance it out. That really makes me think. Looking ahead to those who are going, what, what are you talking about? This December there's a conference coming up where you have a group of people who are really into this, and that's our friend Amy Hinote and the Darm Conference, which will be down in Sandestin again this year the first few days of December. So mark it on your calendars if this sounds something like you want to dive into a little bit.

Speaker 2:

Absolutely. She always brings great content, especially for people like me who don't necessarily understand everything in debt and revenue management. It's a one-stop shop for it all. So, tim, if we're thinking about this trend of a shorter booking window we've talked about what we think has precipitated some of that change. I think we also have to look at the other thing that this summer has really brought as a trend, and a key is that we're now dealing with a very financial, conscientious consumer. Last week, I know that the Washington Post just came out with an article and they found that Americans are spending 25% less on vacations. Have you noticed that as well, tim?

Speaker 1:

I actually get the Washington Post the paper. When's the last time you read a paper, tony? One of the other things I saw was airlines are seeing more empty seats than they've seen in quite some time. People are not taking that airfare back to that conscientiousness on the consumer end of things. But yes, I'm seeing not only people are using their credit card to get the points and being hesitant to make that call, but I'm also seeing that when they do make that call and they make the booking and maybe we actually are talking to the guests and they ask about the week and the price and the next thing they ask now what's your cancellation policy? Again, they want to have a real comfort level and they really scrutinize cancellation policies more than I've ever seen.

Speaker 2:

And again, I think that the industry is training them that way, with so many options for a cancellation, but that financial conscientiousness is just producing a very risk averse consumer and guest, and so you need to really be aware of that and I do want to add into to the rewards points.

Speaker 2:

And so you need to really be aware of that and I do want to add into to the rewards points. That's another thing that I think overall, throughout the world we're training in terms of travel and started with credit card points. But having consumers, having guests, utilize credit card points for travel I've seen that so much this year. That's how we've driven a lot of our flight to the feeder markets that require flights to come into our area. I've been using that. We've actually seen in one of our businesses we list on Marriott Homes and Villas and we've already surpassed this year in bookings and the year's not even over yet and we've seen about a 15% increase in revenue from listing because so many of those individuals are using points to rent out our homes in that specific market. So Expedia also sent in a report recently that was 82% are interested in using points. So just know that, not necessarily that you need to be using points within your program, but understand that a lot of your guests are reaching you by utilizing the points to come and see you.

Speaker 1:

Is there a marketing tactic that you think we could employ to maybe help that out?

Speaker 2:

I think that there's great emails to be used. Catchphrases like cash in those points come and visit us, work with your marketing team, so then it also looks like a value add. You know that they're spending on the property but to get there they can utilize the points. So you're giving them this idea that you're cutting the cost for them. But work with your marketing team and really send out those direct email marketing campaigns as it relates to those rewards.

Speaker 1:

I love that. I also love to hear from you folks out there listening. Have you been able to do something this summer that we could pass on to our fellow listeners about utilizing points and taking advantage of this whole more scrutinizing guest Speaking of scrutinizing, one of the things that you told me about before we started recording was a new trend to me, and that is the decision-making is changing with regard to vacations. The people are still coming and they're still paying, and so on, but the people who are behind the decision to come is changing. Tell us about that.

Speaker 2:

Tim, this is so crazy to me. So I serve on our local DMO board and this survey was brought to us by our research and data development team back in the spring and specifically for the Walton County in Florida, which is a very dominant vacation rental marketplace, and they found that in three and five, teens are involved in the planning of vacation activities and destinations and that is a staggering high number, high number, and I also saw that Amex, as a part of their global trends report, also said that 68% of Gen Z and millennials are utilizing their children and allowing their children to help make decisions on location for travel. So we've seen that a lot, just as an overall area, that we need to be able to provide activities for children, teens, but also think of it too, if you're multi-generational, that you have some of your older children coming in and making those decisions, so it's not always the matriarch or the patriarch that is now making those choices.

Speaker 1:

I was going to ask you if Henry and Mills were involved in your travel decisions, but then I stepped back and went. You know they are to an extent. How many lacrosse tournaments have you been to? How many soccer things have you had to do? Yeah, so that's part of the decision-making process too, right.

Speaker 2:

Oh gosh, absolutely, although I'd say those accommodations are not where I'd like to go spend all of my time.

Speaker 1:

Yes, indeed, I've been to more than my share of cheer competitions and baseball. We're exactly on the calendar where we plan the year out. But you know another thing that's happening that I just experienced, and that is different types of groups traveling, like girls trips. Or in my case, I took a guy's trip. We went on a little golfing adventure. That was kind of cool. And my wife just got back from a girl's trip and to the tea of what this podcast is about today, I was like pushing her. She knew she was taking this trip six weeks in advance, didn't make any arrangements other than the flight and we're a week before. Have you got your rental car? Do you have accommodations? No, we're going to work it out. There's going to be stuff available, don't worry.

Speaker 2:

So that's happening. Yeah, absolutely. And so when you think about in your marketing campaign I know that we do this a lot too when we start doing some videos and pictures, have on there some of those groups that you know will travel to your destination, those smaller groups, the guys trips, the girls trips, the mother-daughter trips, whatever that may be and have some of those stock photos so that you can run some of those campaigns throughout the year and press them for views, because those folks are very willing to tell about great experiences.

Speaker 1:

I've seen more great reviews from those girls groups this year than I have from the traditional travelers, so that's terrific. So we've established some trends about what's happened this summer. One of my key staff members here has a saying that proper preparation precludes poor performance. Five Ps right, and so making sure you can do what you can do in advance I think is also something we mentioned here getting the work done in advance because you know they're coming.

Speaker 2:

That's such a great point I want to shout out to Pretty Picky, the company that is in Cape Cod. So I did a elevate session on how to earn more money and drive more revenue in your maintenance program and they have totally locked it in in terms of preventative maintenance and home care and driving revenue in that department. And so I took a little piece from their playbook and we created a spring cleaning AC preventative maintenance program in-house and there were several things that we did there. One, we were able to really look at the ACs, provide some additional cleaning and then, two, we were able to review the house and the property to make sure there were any if there were any additional work orders that we could go ahead and give it a little fresh up before the peak season. And man, did that really drive revenue and, knock on wood, we have had such a better peak season AC shutdown than we've ever had. So it has been a huge game changer for us and was really grateful to that session so that I could learn a little bit more.

Speaker 1:

That is well-timed. Not even an hour ago, I had one of my key maintenance techs come in and visit with me and he was lamenting the fact how, this summer particularly, it's on the top of the mind. So that's why we're talking about this summer. More deferred maintenance, we shall call has been done by owners, where he's having to fix rollers on sliding glass doors and screens that weren't properly prepared and things like that. So we are amping up our preseason game next year to include doors and decks and appliance analysis and things like that, because this has been the summer of dishwashers, washing machines, microwaves and routers going down.

Speaker 2:

And it never fails. Every summer it's one big item. You think that you've cleared it out and you pat yourself on the back, and then the next summer they're all experiencing the same issue. So if that's the case, go ahead and plan, like Tim, ahead of time and add it into your preventative early low season maintenance program.

Speaker 1:

And if I can get a head nod from our listeners out there on this one, the ones that have been in business for a while it frustrates me to no end. That owner knows that that door is not working properly, but he doesn't choose to fix it in March or May. He waits until a guest complains in July. Right, it's always that air conditioner that broke and you call the owner. Yeah, well, I was just hoping it would get through the season. You know, I know I needed to replace it. Well, you just inconvenienced your guest and you lost $2,000 in a refund because of it, dude, so let's get on it.

Speaker 2:

I remember we had an owner once where there was like the carpet was really messed up in one corner and we had a note for several months that every time someone checked in we had to say we know it's not your fault, we want to let you know, we have it scheduled, but the owner wasn't willing to do it until a certain amount of time. So I've experienced, I get that and I here in solidarity, Tim.

Speaker 1:

Yes, and it seems to be always the ones where the owners put a long-term block in place and they end the block the day before the first check-in. So we're all like, okay, let's see what this one's going to be like, right? Oh boy, you guys feel my pain out there. So that are the trends that I see. Oh, wait a minute, there's one more that I'm seeing that you put on here that I think we need to address as well.

Speaker 2:

Yeah. So this one, I mean I told you about putting something in a cart and being told I look pretty and get a little coupon. I feel like this summer was the year that I turned pretty. I have never been courted by more new AI vendors and phone calls than I have this summer. Every time I look at my phone throughout the day, there's I shouldn't say every time, but there's been a lot of persistence, which I like to some degree. But again, we're in peak season, not the best time. But on another side too, we've had to break up with a few vendors this summer and I think you've had that as well.

Speaker 1:

Yes, does it really do what they say it does? Oh, that's in development. That's the key phrase. Right, that's coming. It's tough. We're just out here trying to get it done. So there's a lot of bluster out there, and so we talked about Darm before. One of the key things when we go to those conferences is I have to have one or two employees run interference for me so I don't go and buy those shiny objects over there in the corner. It's cool over there how do we give that a try.

Speaker 1:

No, tim, we're not going over there, not going to talk to those people.

Speaker 2:

You have a handler.

Speaker 1:

I have a handler.

Speaker 2:

Yes, indeed, Well you know someone really wise once told me and I won't say his name, because once I start saying it, I'm sure you can identify exactly who I'm speaking about but a wise individual once told me that a vendor should not be jumping into my ledger to make their profit. It's not going to be a sustainable company. So, one, because they won't be able to take over the market share, because most people won't be able to afford their services. And two, a PMS will eventually replicate what it is that they're providing and make their specific service obsolete, and so we've seen that a lot. And when you look at some of these different AI vendors that are coming out or vendors that are starting to court, you really think through how much this is exactly gonna cost and it coming into your ledger. But then in a couple of years, is your PMS system going to just take it over?

Speaker 1:

Yeah, Great point. I'm just having flashbacks of some of the messages I've gotten this summer. First of all, I'm not sure how they got my cell phone, and then I'll get not only calls but texts. Hey, Tim, I see you're in the market for so-and-so. What would make you think that? No, I'm not. And then the other thing is, if they're doing something, is it something you could do on your own? Maybe? Think of that aspect of it. And don't you love group vendors, these people that touch base with you and go? Hey, just wanted to ping you and let you know that I'm available for a meeting Tuesday at 2 or Wednesday at 3. Which fits your schedule better? I know you want to talk to me about this new product I have.

Speaker 1:

Yeah, I guess it's something close, I guess, is what they call that.

Speaker 2:

Yeah, well, yeah, or if they're in the market and hey, I just want to stop by, right, don't stop by without a care package. How lucky am I that they're here? How, and you know, not to say because I do love a lot of our vendors so much, but I do think that it's something that everyone just has to be really conscientious about. And again, like I said, this was also the summer of breakups. They're individuals that I absolutely love and, unfortunately, their programs no longer fit for us, so we had some websites that we had to move over because they were just not converting in the way that they needed to be during this economic time frame, and that was a business decision. So we had some pretty sad breakups this year as well I'm sure you tried to renegotiate where you broke up right.

Speaker 2:

Yeah, always renegotiate. There's always some wiggle room, I think.

Speaker 1:

Yeah, but that is a good operator that looks at all the sacred cows, making sure that they truly are sacred. I've mentioned as well as you're talking about experiencing breakups and being courted. This is also the time of year where property owners are looking to be courted and you might be looking to break up Back to some of the examples I gave you before. Is that owner really a good partner? Because we're in business together and I always make that point and you guys have heard it before and I'm going to say it again it's not their home, although Tiffany likes to use that word, tiffany likes to use that word.

Speaker 1:

I say to my property owner the moment you accepted the first dollar in rent, it no longer became your home. It is a commercial domicile. You've opened a business here and we are in business together and we need to operate that way. They're being abusive to staff, whether they're not doing their part on keeping up the investment or whether they're just a general pain and they have maybe all expectations about what you can do. This is the time to look at that relationship and consider a breakup, because not all relationships are great and some are better afterwards.

Speaker 2:

And, tim, there's probably a subset A from that too of some of the things from the summer. But a lot of our properties that did really well last year did not do necessarily as well this year. Or some of ours that didn't do well last year did really well this year. So really, looking through that, as you have these conversations of the breakups and then maybe the owners you want to get back in touch with, that's important too, because this summer definitely was very different in terms of who were our producers and who weren't.

Speaker 1:

I am thinking about one particular property owner that dealt with here the last few weeks. We'll say I won't pinpoint it we had a situation where a porch swing had fallen at the property and the guest was injured, and so that's pretty serious, right? And so we removed the swing and everything's fine. We're moving along and literally like three weeks later, the owner goes where's my swing? You didn't throw it away, did you? That was a very expensive swing. Don't worry about asking how the guest is with their broken tailbone. That's a relationship we need to review. Wow, that's what your first thought was Where's my swing? When somebody was injured and taken to the doctor, yeah, that gives me anxiety of the liability.

Speaker 2:

Yes, that's what we're in business to protect them.

Speaker 1:

That's what my first words were to them. So we covered some keys the booking window shorter and of course, people are very conscientious now, financial conscientious consumer. That decision maker is changing. There's something you may not have thought of, that low season work before the season start, essential. And then, of course course, the breakups and you being courted. Those are our summer 25 trends. Do you have some we've missed? Drop us a line. Come visit us at the Vacation Rental Key with T and T, don't forget to spell it and at the end you can communicate with us there. You can see us on social. We'd love to hear from you and we're getting to the season, the conferences are arriving and so you will see us out and about and we hope you stop by and say hello and tell us what you like about the podcast and what we might do for future episodes. We'd love to hear from our folks out there listening, wherever you are.

Speaker 2:

Thanks guys, we appreciate it. We hope that you've had the really highest of highs, but not the lowest of lows this summer. Remember we're here for you too.

Speaker 1:

Okay, we'll see you on Labor Day. So long, everybody. We'll see you next time.