The Vacation Rental Key with T and T

Episode #11 - Your House Just Booked 24 Hours Before Check-in (And Other Industry Shockers)

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The vacation rental landscape is transforming before our eyes, with shifts that started during pandemic times now cementing themselves as permanent fixtures in our industry. Hosts Tim Cafferty and Tiffany Edwards dive deep into the most significant trends reshaping how successful property managers operate.

Remote work flexibility has fundamentally altered travel patterns. Though some workers have returned to offices, the ability to work from anywhere remains firmly established. Smart vacation rental managers are capitalizing on this by ensuring properties feature proper workspaces, reliable high-speed WiFi, and marketing that specifically targets these "bleisure" travelers. As Tim notes, even transforming underutilized spaces into dedicated office areas can become a powerful differentiating amenity.

Perhaps most striking is the dramatic shortening of booking windows. Both hosts report seeing timeframes cut in half compared to previous years, with Tim sharing a recent booking made just 24 hours before arrival. This requires a hands-on approach to pricing strategy, adjusting rates for remaining inventory without undervaluing properties. "This isn't a slash sale," Tiffany emphasizes - there must always be a threshold below which prices won't drop.

Today's guests also demand more flexible cancellation terms before committing to bookings. While historically some managers maintained strict policies, both hosts have seen positive results from more guest-friendly approaches. Booking platforms are even incentivizing flexibility through algorithm benefits. The numbers consistently show that despite occasional cancellations, the net result of more flexible policies proves positive.

Communication expectations have similarly evolved, with guests strongly preferring text messaging over phone calls. They want control to initiate contact when convenient while expecting prompt responses. Implementing effective texting systems with personalized automated responses has become essential, though interestingly, proactive welcome calls can still create positive impressions precisely because they're unexpected in today's text-dominated world.

The hosts also discuss how social media influences guest expectations, the strategic use of influencer partnerships, and important new FTC regulations requiring transparent pricing across the vacation rental industry.

These trends aren't temporary - they represent permanent shifts in guest behavior. Success now depends on adapting to meet these evolving expectations. Visit TheVacationRentalKeyWithTNT.com or find us on social media to join the conversation and share your experiences navigating these industry changes.

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. To success in the vacation rental business. We're back. Welcome to August. Everybody Can't believe it. It's already here Before you know it. Labor Day will be behind us and we'll be talking about conferences coming up. We wowed you last time with amenities that will wow your guests and we're back to wow you again this week. Diff.

Speaker 2:

I still am trying to compartmentalize that. It's August and then the holidays come and we're now at the end of the year, right? So I'm excited to get into what we've got on the table for today. We want to talk about trends.

Speaker 1:

There's a lot of trends out there right now. In fact, we might do a couple of episodes on trends. There's a lot of trends out there right now. In fact, we might do a couple of episodes on trends. There's a lot of trends this summer that have popped up that I didn't expect, but generally trends in the industry. Maybe you know some of these already, maybe these are going to be new to you, but we've got some points here that I think are worth you listening to and maybe get a pad and paper.

Speaker 2:

Absolutely, and the most important part about these trends is you probably are aware, but we're going to dive a little bit deeper on how you accommodate these trends within your business and make sure that you're capitalizing on them.

Speaker 1:

Let's get into it. We've got what? I don't even know how many we've got on here, but I think I see at least two, three, four general areas. And let's start at the top. And that is a trend that started after COVID Working out of the office, working at home, we're not in the office as much as we were as a general population. Now, true, people are going back to the office, but it's like a genie out of the bottle. You can't quite put it back the way it was supposed to be, and so we, as innkeepers and accommodations professionals, need to be prepared for that. What comes to mind on this?

Speaker 2:

Tim, it's so important. Just as you said, it's not like it was before, where everyone is working from home. However, there is a lot of flexibility for people to take some time to work from home, and you need to make sure that you are capitalizing on that. So one of the ways that you need to be doing that is all of your content that you put in for your listing sites, making sure that you have information about your high-speed Wi-Fi, you have pictures about a desk, or you make sure that you communicate with your owners that they need to have a space that's available for a desk and for that high-speed Wi-Fi. You need to make sure you target all of that marketing and that listing content. The other part, too, that's really important we've done this in the past is that the OTAs really did a great job of marketing this sector, this be leisure sector. So really understanding what they're putting out there in content and trying to replicate it a little bit within your own system.

Speaker 1:

Yeah, and two things come to mind. One is this is an opportunity for some recommendations regarding design components in your properties. There's that wasted space that the owner doesn't know what to do with, whether it be a crow's nest at the top of the house or the room off the living room that is kind of a clutter area of games and puzzles. They could make it into an office area and it becomes an amenity. So keep that in mind. The other thing about flexibility I told you my laboratory is my children. I have those young working class folks out there, including my son who is an attorney and he lives in Tennessee. He works in Kentucky, so he commutes back and forth and his employer has allowed him the flexibility to, of course, come in the office, but at least one day a week he can work at home or he could work at the cabin at the lake if he needed to as well. So I think we're finding more especially, younger professionals have more flexibility where they can get away for three days and maybe come and visit your vacation rental property.

Speaker 2:

And Tim. The other thing, too, is that you really need to understand your area. So if you're in an area that accommodates smaller conferences or conferences in general, making sure that you have the connection and marketing to market your properties as a stay for those individuals who are attending the conference and maybe bring their family with them and extend that timeframe off property from that conference. There's a lot of opportunity there as well, and I know that for our business out in California we have a very large feeder market for Texas. Well, a lot of those individuals that we market to like to get out of the Texas heat during the summer and they have the flexibility to come and stay in California for a month at a time and work and kind of go back and forth.

Speaker 1:

Wow, great, I need some of that work. That's great Me too. One last point on that as you market this bleisure content, make sure your listings are on point. Pictures are really valuable. I sense an episode coming in our near future where we look at some listings and some listing fails One of my favorite things to do. Don't be one of those we pick on where you have maybe a computer in the screen. You remember that was amenity, like 15 years ago. It has a computer dear. Oh, this is wonderful. No, we don't want that, but we want a nice workspace. Make it inviting, make the pictures look good.

Speaker 2:

Please don't be the large computers you know from yesteryear. It's like the flat not having a flat screen TV.

Speaker 1:

Exactly, we used this 10 years ago. We're not using it anymore. Let's put it in the rental house. Oh boy, yeah, okay. Anything else on the working from home aspect as a trend?

Speaker 2:

I will add in your property, making sure that you have obviously the Wi-Fi information in almost every room framed and up and ready to go.

Speaker 1:

Excellent. Okay, another trend we want to talk about here for a minute is that immediate satisfaction, for lack of a better wording, particularly as it relates to pricing. We are seeing shorter booking windows. I know you out there are nodding your head. People want those last minute deals. So what kind of trends do we think of when we're thinking about adapting to this, or what can we do to adapt to this trend? Tiffany?

Speaker 2:

that's great, because we're seeing some numbers this year that I would have never thought possible. We're seeing booking windows from last year to this year cut in half. I'm seeing booking windows shrink for our location, hawaii, which I never thought was the case, but I think it goes back to this culture that we have now of immediate satisfaction. I want something. I want to Amazon prime it, I want to receive it the same day or two days later, and so you really have to be on top of your rates and adjusting for those rates. You really need to market those open two to three day windows that you may have and I know that we've mentioned this in previous podcasts, but, knowing your owners that are comfortable with opening up some of those windows, also with some of your larger homes, if you wanna shrink in some of those days and open up some of those times for your guests as well, those are great opportunities and ones that some of those times for your guests as well. Those are great opportunities and ones that your guests are looking for right now.

Speaker 1:

Love that and I 100% agree with you. I have never seen so many last minute bookings. Last minute to me is within 30 days, but I'm talking. I had one of my houses book this past Saturday for a Sunday arrival unbelievable. Somebody made the plan 24 hours before they arrived. But that's what we're dealing with and you better make sure your pricing is available for those folks that they feel like they get a good deal on that. And the other thing don't do it automated. Make sure you're in there and you know what's going on. Another thought I have on that is making sure you're communicating with your property owners so that they understand this trend and they are not weirdos because their house isn't booked 48 days out. This is what we're doing, folks, and we need to make sure everybody is aware and we're handling it professionally as possible.

Speaker 2:

Tim, I really think this trend is here to stay. I really think that it's a big cultural shift and I think that, to your point earlier, I think it really depends on you being involved on the pricing and on the rates, with whoever helps with your revenue management. That is going to be key from this point forward.

Speaker 1:

Do you mind sharing what kind of philosophy are you thinking on rates? Is there a certain time frame where lights go off? We're green light here. We get here it's a yellow light. We get here, it's a yellow light. We get here it's a red light. Do you have a philosophy about how you adjust pricing?

Speaker 2:

Yeah, that's such a great question. So I think it all depends on what time of the peak season that it is. So that is a very large component. We also weekly go through and we really drive down to house by house what's not performing well. Before, where it would have been two to three weeks out, we would have been more concerned. Now we're looking kind of a week out. But it also depends on which company. So there's one company that we're more concerned about occupancy and so we are considering daily dropping that ADR for that occupancy. So our inventory allows that For some of our other properties we aren't booking or aren't pressing that red button until much closer. So, looking at it more so a week out and that's based on that property by property and overall what we're coming in for a revenue for the business.

Speaker 1:

Yeah, I still can't get over that booking. I'm not sure I ever will, because I had resigned myself to the fact that this house was not going to get booked for this week. This is one of my personal houses, by the way, so not just in the inventory, it's my house and it was one of only three that weren't booked for the week and I had already prepared for my wife. I hey, we'll have an opportunity, we can go in and freshen it up and hey, maybe we can spend a night there. And then, lo and behold, literally the morning of the person checking out and the vacancy to start, I get a message you have a booking and I just I'm dumbfounded that somebody would not plan further in advance. But again, it's a trend. Better adjust to it in advance.

Speaker 2:

But again, it's a trend. Better adjust to it. And, tim, the other important point of that, too, is don't undervalue. This isn't a slash sale. You still want to be able to drive financial gain from whatever this booking is, so don't cut yourself too far or too low, and that's really important for you to understand when you look at pressing that red button, because there is a point that we will not go below.

Speaker 1:

Yeah, there's some great tools out there. We've talked about them before. Make sure you're watching them. See what the ADR is doing in the market. Make sure you're not undercutting yourself, but make sure you're letting people know that you have availability for from five properties. Another thing I think we're seeing is those folks are waiting because maybe cancellation policies are driving them and they don't want to risk it. What are you seeing on cancellation policy trends?

Speaker 2:

That is something that the consumer is looking at constantly, and we're in this flux where, especially in our industry, where so many property managers have a different cancellation policy than what an Airbnb or what a Vrbo policy would be. We've done really well on changing our cancellation policy this year to be a little bit more accommodating towards the guest. We've seen a significant increase in reservations as a result, but that is definitely creating a very significant trend towards finalizing bookings for consumers and for guests.

Speaker 1:

People can blame it on whatever, whether it be the economy, just the general nervousness about where they are in their lives, but they don't want to risk financial loss. And I have had to face this because we had the strictest cancellation policy in my area. But I see now it's loosening up and Vrbo has some rewards available to you if you do have those more flexible cancellation policies in terms of how you show up in the algorithm and that sort of thing. And they really the guests, they're demanding this. It's not just that they want it, they're demanding it.

Speaker 2:

Yeah, it's another one that's not going away and it's clearly been adopted by so many in the tourism space and industry. And I will say we've ran the numbers in several businesses where we've changed our cancellation policy and we've just done really well. As it relates, you're still going to have some that cancel very close to the time frame. However, overall, it's still a net positive for us.

Speaker 1:

Okay, so there's some trends about bookings and the immediate satisfaction. Speaking of immediate satisfaction, how about the ability to communicate with our guests text and social? What are your thoughts there?

Speaker 2:

This is such a good one, another one that is here to stay. Text messaging is so important for guests. I think that if you really take a look at yourself, how many times do you want to be on a phone call and be moved around from individual to individual or hear any of the waiting music, and not to say that that's necessarily your company? But I just think that overall, we have a shorter fuse for our guests, especially if there's any type of issue. I also think, too, that people are wanting to get away and not be encumbered by a phone ringing, and they want to have the ability to decide when to answer. But I think also, when they have an issue, they want an immediate response to send out that they can control, and so that texting capability is so important to have for your guests.

Speaker 2:

Texting capability is so important to have for your guests, whether that be through something that you use internally throughout your office. We use a software. It's vital for us, it goes through and it keeps all of that information for our staff. But I like to think of it, too, as text messages and information that you can have available by a text is similar to what they would see on a website or add-ons. I still don't think it replaces like a welcome. How are you to the area, call and maybe leaving a message, but other than that, everything needs to be a text capability.

Speaker 1:

Agree completely. I had experienced this past weekend that I just was thinking of, as you were describing that, where I was monitoring the texting. As I came in early in the morning I was the only one in here and so the person had complained about garbage pickup. It wasn't done and I apologized and I did the A train agree, apologize and act. We're so sorry. I agree the trash shouldn't be piled up. We will get someone by there and the person responded back. Have you not seen the string of messages that I've left on this? And I scrolled back and saw that she had texted four times overnight. Well, nobody saw the messages. Sorry, didn't check my messages at 2 44 AM, but we're here now. This goes back to the immediacy thing. Again, people want to know you are standing by and ready to solve whatever problems they have.

Speaker 2:

And even further on that. Tim, you still need to make sure that if you have an automated response, that it's very personable, yes, and it doesn't read like a chat GPT. So that's really important too, so that if it does come after hours and you do have an automate, you still make them feel warm and fuzzy.

Speaker 1:

I love the idea of that call it kind of reverses where you were talking about getting lost in that maze which I'm sitting here dreading. I know I have to call Spectrum Cable and I know I'm going to be on the phone for an hour. I have no idea where in the world I'm going to end up, but I can't get it done via text or on the computer so I have to call them. So I'm dreading that. But the interesting twist that you just threw in there is that a welcome phone call is a pleasant surprise. It's an actual human welcoming me. I'm not pissed off that my phone's ringing. Why don't you just text me? Oh, I'm here from XYZ Realty and I want to make sure you know that we appreciate you being here.

Speaker 2:

What a great idea. Proactive versus reactive, and so then, even moving on the influence of social media, texting technology I think this trend is also here to stay, and that is the overall influence of social media and, what I like to think of, of the social jealousy, so all those influencers who like to post in your area of these idyllic vacations and create a lot of jealousy for anyone else who's not on this trip. That is something that you want to also look at trying to recreate.

Speaker 1:

My former co-host, Sarah Bradford, shouted to her. She used to call it that Instagram moment. Do you have an Instagram moment at your property? I just built one in front of our office. We have this beautiful new stallion that's bedazzled in reflective tile and I've already seen like it's been unveiled for five days I think it is now. I've seen probably 10 people stop and take a picture in front of our stallion. Look at this idyllic situation I am in.

Speaker 2:

Look at me, look at what I'm doing yes and you're not and you're not. And the other part about that, too, is really making sure, when you're developing your marketing plan, how much are you utilizing influencers and making sure that you target influencers that really are the demographic of your feeder markets and your company. I know, and Tim, you probably get this all the time of people who say, oh, I'd love to come, I'm happy, I'm happy to come and stay at one of your properties and post three times. Well, my next door neighbor has more followers than you. I'd rather have them stay there. So it's really driving in what influencer you're trying to target, what influencer, what they can create and the content and how much activity they have on their profile and within their account, and really cultivating that trip with that influencer, because that's really important as well.

Speaker 1:

Yeah, our local visitors bureau does a good job with that of making sure, when those high-profile people come to town, that they do have things to do and they'll actually offer it. Hey, we have this person and this is their profile and this is what they're reaching. Would you be interested in hosting them? I love that part of it, instead of me having to do the research and a wish and a hope, as we used to say back in the day. One other trend I think we need to touch on here and that is related to us as individual innkeepers.

Speaker 1:

I've used that word a lot here in the last month or so. Individual innkeepers I've used that word a lot here in the last month or so. There's a trend. It's a law on the Consumer Protection Agency about transparent pricing. I don't know that everybody's on board with this yet. Tiffany, the fee disclosure thing we all go to the hotels and they charge us that resort fee and we'd all get PO'd about it. Well, they did something about it, but they also extended it to us as well. We need to make sure we're transparent in our pricing on our websites and so on. Right.

Speaker 2:

Absolutely so.

Speaker 2:

This law was passed back in May of this year, 2025. And I don't think a lot of people are aware of it, but for the first time, the short-term vacation rental industry was included in a full hospitality. The short-term vacation rental industry was included in a full hospitality ticket sales experience decision from the FTC, and so it is extremely important that you disclose what your fees are, that you are following along with what the Federal Trade Commission has put out and requested, and I think that overall consumer transparency is going to be a very important part of what it is that we do, because it's not because of us specifically, but overall of the industry. There's just been so much consumer backlash of here's my rent and then when you go to the end and you probably more specifically, we could use, as a hotel, $40 a night for that to leave your car, $20 a day for Wi-Fi, whatever it may be, we're going to be lumped into that as well. So you need to be making sure that you're aware of that FTC decision and then also that you're following compliance.

Speaker 1:

I was very pleasantly surprised to see the majority of my competitors and us here in this market are compliant on this, but the ones that aren't stick out like a sore thumb. Now You're not doing it right, so make sure you're doing it right.

Speaker 2:

And Tim. The other thing for that, too, is that you then look like you're trying to hide some of your costs. So even if a guest, when they look at your site, doesn't understand that this is actually federal regulation, you look like you're hiding a bunch of information, as opposed to having a site that has it listed out.

Speaker 1:

Yep Can be a competitive advantage. Make sure you get on board with that. Okay, any other trends we need to talk about here?

Speaker 2:

Those are the ones when we look at trends here in the last several years. These are the ones to me. They are not going away. So, as Tim said, if you have your paper and pencil, make sure you write some of these down, because they're not changing.

Speaker 1:

Gave you some more keys to the vacation rental industry and hope that you enjoyed that. We'll be back next time. Maybe we can talk about some trends for this summer. I've got some in mind. It's been a rough one.

Speaker 2:

Me too, tim. As we said earlier. I'm surprised that it's August, but I have just a tad bit of PTSD. So maybe on the next episode we can share what we've learned.

Speaker 1:

Oh, that's always healthy. Okay, Well, until next time, folks. I hope you enjoyed this one. We'll look forward to seeing you on our website, TheVacationRentalKeyWithTNTcom, or look us up on social. Send us a message there and give us a review. It helps. I appreciate all that you do for us and we will be back to do it for you again next time.

Speaker 2:

So long, everybody. Bye guys, Thanks for listening. We'll see you next time.