The Vacation Rental Key with T and T

Episode 6: Mastering the 100-Day War: A Vacation Rental Manager's Guide

• Tim • Season 1 • Episode 6

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Memorial Day marks the unofficial start of peak season for vacation rental managers across the country—are you truly prepared? In this tactical episode, we unpack the essential strategies for navigating the "100-day war" that defines our industry's busiest period.

From comprehensive housekeeping preparations to staff motivation techniques, we share battle-tested approaches that successful managers use to maintain quality and sanity during the summer rush. You'll hear practical advice on staging pre-season training sessions (including our innovative property scavenger hunts), creating effective communication systems between departments, and ensuring your billing processes capture every billable moment—a critical factor in maintaining profitability.

The conversation goes beyond just operational readiness to address the human element of peak season management. We discuss creative recognition programs that keep staff motivated when the pressure is highest, including appreciation events, strategic communications, and performance incentives that actually work. One of our favorite tactics? A perfect attendance drawing for big-ticket prizes that significantly reduces those dreaded Saturday morning call-outs.

Whether you're already in the thick of your busy season or planning ahead for next year, this episode provides concrete, actionable guidance from managers who've learned these lessons through decades of hands-on experience. The difference between a chaotic summer and a profitable one often comes down to preparation and systems—let us help you build both.

Ready to transform your peak season experience? Listen now and discover why proper planning truly is the key to profitability in the vacation rental management business.

Tim Cafferty:

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.

Tiffany Edwards:

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.

Tim Cafferty:

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

Tiffany Edwards:

Welcome back for another really exciting episode. I cannot wait to dive in today, Tim.

Tim Cafferty:

Well, it's a good thing, because the season is upon us and I'm already into it, so let's go.

Tiffany Edwards:

Today we're going to talk about what all you need to do to get yourself ready for peak season, and there's quite a few lists that you need to be checking twice.

Tim Cafferty:

Amen, sister, we're into it. This podcast is being dropped on Memorial Day, so I'm sure some of you said a little late on this, but better late than never. And we've actually broken it down to the three areas, like our takeaways, and so we've got three areas. We've kind of organized your organization for the season. The first one would be preparing for the season. Then we're going to talk about the season itself as we get going and then maybe the post-mortem after the season is over what not to do and what maybe you should do. As you've learned over the next 90 or 100 days, I am ready to roll, and I know you are too. As you've learned over the next 90 or 100 days, I am ready to roll, and I know you are too.

Tiffany Edwards:

So let's go ahead and get started on preparing for season. So, tim, how long do you think that you really need to start communicating with your staff and reviewing some of these items, looking at that peak season timeframe?

Tim Cafferty:

Well, you're going to get me on my soapbox here. I would say that it starts during budget time, which should have been several months ago, maybe even last year, preparing for this year what are our expenses going to be, what's our income, how much payroll and so on. But for me, our season, traditionally Memorial Day to Labor Day we'd love to say it extends on either side, but the reality is that's go time right. And so, as we prepare for this past weekend, if you will, we started pretty much in January, tiffany, as we thought about things like the materials we're going to need, the staffing we're going to need, the training that we're going to need, and it does take time to get that just right. How about you?

Tiffany Edwards:

Yeah, absolutely. And one of the things that we do in preparation of that staffing and one of my absolute favorite key takeaways that we do for all of our businesses is a housekeeping meeting. So to make sure we build in. All of our housekeepers are contractors, but we want to build in ties and relationships with these housekeepers so we know during peak season they're going to show up. We do have some housekeepers we keep all year round, but obviously during the peak season we need a lot more.

Tiffany Edwards:

So we put a fun little luncheon together. We usually have our owners or our general managers there helping cook hot dogs and hamburgers. We sit all the housekeepers down at the table anyone who's reached out to us, any of our housekeepers who have been with us for a very long time and we really talk through what our processes are. We talk through what expectations are. We make sure that it's a really fun event for these individuals and I think that that really helps build the expectation. We also help too, for a lot of the housekeepers talk through how they can create their own businesses and provide them supporting materials so that they can be a contractor.

Tim Cafferty:

That's really important, and many of you out there use contract services to clean your properties. I use employees, and there is. You out there use contract services to clean your properties. I use employees, and there is a very distinct difference. Employees I can direct to do whatever Contractors. You can give them your guidelines, but you really shouldn't have that control over exactly how they do the job. You can give them guidelines and that meeting that you described is great For our purposes.

Tim Cafferty:

This past weekend, for instance, memorial Day weekend, we had five training sessions for our staff Friday morning, friday afternoon, saturday morning, saturday afternoon and Sunday afternoon, whether it be a quality control person or one of our employee housekeepers. We went through all the chemical usage, we went through our standard property appearance handouts. All this takes time to prepare, and then the one that I thought we really were good on this year was we went to a property after the meeting and we had a scavenger hunt, so to speak, where the team that was there for that meeting had a checklist and they could find 17 things that were incorrect in the way that we've prepared the property. And we went there before, of course, and purposefully didn't put a towel on a bed or didn't put the soap out in the proper position or the coffee maker was not in the right spot, and whoever got through that list and found all 17 items first got a little prize. It was pretty cool.

Tiffany Edwards:

I love that. We've done that before too, where we've hidden gift cards in places where they should be looking. But don't always do that. I love that incentive component to it.

Tim Cafferty:

I have a quick story there. I used to do that years ago. I would go on properties and I would hide money in the toaster and the oven and so on, and then we had guests calling. We found a $20 bill in the oven. That was not exactly what I had in mind. Oh, so we've refined that.

Tiffany Edwards:

That's a good one. The other thing, too is when you look at from a contractor for services, you really need to know who your preferred vendors are Absolutely. For some of our markets, acs going to go out peak season where you have nowhere to move the guests. You need to make sure that you have someone on speed dial to help in any of those areas. That could be very problematic for your owner and, more importantly, your guests. And so who's going to come out and answer the phone for you after hours and do you trust their work?

Tim Cafferty:

So when we talk about preparing for the season, I hope you all already have, if you do, welcome bags. I hope you ordered those months ago, because the tariffs are in place now. You're a little out of luck there. How many soaps do we need? What's your inventory par? Have you done an inventory count on what you have? Do you have re-par, which is what the recommendation would be? And those kinds of things can be done well in advance, much prior to the meetings we're talking about. And then, how about policies? Making sure policies are in place in advance of the season. You've done very well with this, tiffany.

Tiffany Edwards:

Yeah, so we look at our hurricane policy specifically every year. That's one of the ones that I just want to make sure it is very well communicated with our staff. Our number one priority is to protect that investment and a return of investment for our owners and also make sure that our guests are safe. Turn of investment for our owners and also make sure that our guests are safe. And so we need to make sure that anyone that works with us knows exactly what needs to be done prior to a name storm, when there is a name storm and then if we have to return. And then the other policy that we really hone in on is expectations for our staff. During peak season, hours may not look the same. Responsibilities may be shared. There were many times that I just spent days going and stripping beds, even though I was technically supposed to be checking people into the front office. It is a team building timeframe and you really need to communicate that with your staff team building timeframe and you really need to communicate that with your staff.

Tim Cafferty:

Particularly if you have a quick ramp up, which is what we had this year. May was a little softer than usual and, quite frankly, I think we got a little fat and happy in some of the departments where the maintenance techs were able to clock out at 4.30 and get the convenience store on the way home. No, I need you till 6.30 now, buddy, sorry, we're in the hospitality business and that.

Tiffany Edwards:

Nor does it have holidays, Tim, Because I grew up in the business, 4th of July to me was one of the worst and hardest days and weeks, so I've never understood what a holiday off is. But you really need to make sure you communicate that with your staff as well. Whether your summer is your peak season or there's another time that is your peak season, there are holidays that fall, and those holidays aren't necessarily given to anyone.

Tim Cafferty:

Yes, we have names around here for Memorial Day and Labor Day. They're called Mondays, and this year July 4th is called Friday. Friday we are working, baby. Yes, understand that. And then for your full-time, year-round staff, you may need an understanding about paid time off. You maybe are on a slippery slope if you say you can't take off. I think the Employment Security Commission may have something to say about that. But you can certainly frown upon any time the thing that we say all the time is okay, you're leaving, who's covering for you? Because that's the issue, right? All of us have important jobs to do, in whatever role we have, and if you're not there that day, somebody has to take up the slack, and you need to consider that when you take your time off as well.

Tiffany Edwards:

Absolutely, and those are just ways that you can communicate. More importantly, tim, we can add in how do you keep those staff members and your team excited and encouraged during that peak time so rolling into then what looks like season is on us? How do you usually keep those team members engaged?

Tim Cafferty:

Well, I think the frontline folks are the ones I concern myself the most with. Our maintenance techs, for example, who are on the road on Saturday. They're out by 830. And many times they're working till 730 or eight o'clock that same day before they wrapped up and it can get quite tiring. So we put a policy in place last year where we give them a holiday once a month. You get an extra day off this week. Go recharge your battery, Don't do anything involving work, and we've found that to be effective. But you really have to be creative and adapt yourself to the best ones and make sure they're all happy and check in with them. That's the other thing. Do that check-in. How's your heart, How's your mind? Everything good. Are you loving it? Still Not so much, but we used to call it the 100-day war. We only have 33 days left in 100-day war. We're going to be okay. Pump them up every time.

Tiffany Edwards:

Yeah, and again it's that team aspect and camaraderie. You never want to have it. Where it's woe is me. It's a mindset that's different and we're all in it together. We started, on really busy check-in days, providing lunches at a central location, so at the office, so everyone could get together for a few minutes, grab a quick bite to eat. So no one felt like they had to go somewhere else. We could still stay efficient, but we had time together almost in a family aspect. Right, Not everyone takes lunch at the same time, but we're all in the same room taking reservations calls eating. So for any of our inspectors or anyone who's out on the road in the front line had that availability.

Tim Cafferty:

So we told you there were three areas. We're obviously really diving into this prep for the season. A couple of the things on my list for prepping for the season Tiffany and you and I have talked about this offline before. That is, testing your systems, making sure those things are working the way you think they were working and making sure that you whoever you are most of you listening to this podcast are either an owner of a vacation rental company, an owner of a vacation rental itself, or a mid to high level manager. Have you gone into the property with a set of guest eyes to make sure it is what you think it is?

Tim Cafferty:

Tiffany knows I just had an experience where I rented a property in her area and I shared with her my frustration. I feel like I'm pretty good with technology. I could not get to flipping TV on in the master bedroom to save my life. Just ask Deb. She was like are you going to give up on this? No, I am going to make this TV work, but the remotes were not a help and there was no instructions anywhere to find out how to turn on the TV in the master bedroom. So those kinds of things. And then the guest communication how are you communicating with the guest? And are you communicating with the guests? Are you checking in with them during their stay to make sure everything's okay? If you only communicate with them before they arrive and as they depart?

Tiffany Edwards:

with them before they arrive and as they depart. You are missing it Absolutely, especially if they are renting outside of your direct website. You're really missing the boat on your branding, opportunity and loyalty. But, tim, that's such a good point to go into a house and look at it from terms of a guest. One of my biggest pain points is during peak season, so I used to answer the phone. One of the positions I had early on with my mother is during peak season, so I used to answer the phone. One of the positions I had early on with my mother is I answered the phones and I would be almost the maintenance dispatcher. So it was about, I think, 13 when I started that, and so all of the calls that come in are those communication points that we don't need.

Tiffany Edwards:

My AC isn't working. Well, it's not working. You've had the door open and you've been bringing all your things in. My refrigerator is not working. Well, it's not working because you have loaded it with all these groceries and the grocery has been sitting in your car for an hour. So making sure that you communicate that and one of our companies does this. So the refrigerator they have a laminated sticker that says the refrigerator might be a little warm, but we've inspected it's completely clean and disinfected. So please give it some time. So it's not even something that's in a packet where guests will just not think about it, but it's right there and it gives them also a sense of oh wow, this is so clean. Someone's inspected this here and it's laminated and it stays in their refrigerator and that was one of my favorite things in one of our properties that we went into. But it prevents those additional calls that slow down your workday.

Tim Cafferty:

That's a great point about prepping your staff, those frontline people answering the phone. We still do get phone calls and usually they're 911 emergencies from somebody very stressed out about the air conditioner not working properly and the poor gal answering the phone is 24 years old. She doesn't know. You need to train her. You're going to get this kind of call. You're going to get this kind of call. You're going to get this kind of call and this is how we want it handled. Good on you for that.

Tiffany Edwards:

So communication internally with your staff and then making sure what communication you're sending out externally to your guests.

Tim Cafferty:

Check it Very good, all right, so let's transition now. The season is on us, it is Memorial Day, monday. We have all these guests in-house. How about some things here that we can look at? How about extra help Not being caught by surprise on turnover day when you have perfectly scheduled the day for housekeeping? You have all the QC people you'd ever need, and then three of them call out oops, we have 12 houses we need to clean, tiffany. What are we going to do? Oh my God.

Tiffany Edwards:

And, by the way, they've called out in the houses that they've been assigned for the people who showed up at 7 am to get there.

Tim Cafferty:

Always.

Tiffany Edwards:

And they've driven through the night. Yes, with six kids in the car. Yes, and they're very angry.

Tim Cafferty:

Yes.

Tiffany Edwards:

So making sure again that you have individuals that you can call, I think, the other for us as well, for our properties that have laundries. Making sure that we have people who work late into the night to wash and have all of those items prepped and ready to go and have extra bundles of laundry so that if someone else is coming in they can quickly grab. So really looking holistically at your business and saying where are those kind of pain points, where are we going to be backlogged and where do we need people? We also hire more inspectors during peak season for our areas that are peak for summer. We hire a lot of teachers because they work just two or three days a week. It's enough for them and what they want in the capacity and they know the area pretty well and they like the work of being out and about in the community. So that's really helpful for us. But you really need to make sure the housekeeping is really where it starts.

Tim Cafferty:

I would say I've got two more big ones on my list here for in-season preparation, if you will. One of them is does operations know what's coming? And so what I mean by that is maintenance, housekeeping, inspections, whatever ops means for your company. If I had done a check-in report for this past weekend, I would have seen I have X number of arrivals. Great, got them scheduled, we're good to go. If I had done that report again on Friday, I would have found 24 additional arrivals that weren't on the list on Wednesday because we had a last-minute booking. Oh my Lord, do you have a communications process in place? Reservations knew they were coming because we have the lease, we have the payment. Oh yeah, great, the house is open. I booked it. Hooray Oops, we have to go get it cleaned, or we have to go get it inspected, or there's something going on with the door handle. We need to go get that fixed, making sure you have that holistic communications approach that everybody knows. There's a check-in into ABC 123 on Saturday morning.

Tiffany Edwards:

And Tim, I'll add on to that too, because I feel like if owners live nearby and they see that it's open for a short period of time close to it, they'll book it themselves or their family members will come in during that time. So you really need to have your team be prepared for an owner arrival. Especially if it's midway through peak season, that property could look a little different after some significant wear and tear. So how are you communicating that to make sure that those special owners that come in aren't being surprised and you're not surprised by their arrival?

Tim Cafferty:

Well, that's another pre-season thing we could do making sure those owners are of a mindset that, hey, we could book your property 12 hours before check-in. So make sure you tell us when you're coming, because we've all experienced that that's no good. Another one that you may not think of until after the fact is are your billing processes tight? Let's face it, one of our core values is profitability. Don't hide from it. We're in this business as a for-profit agency. Everybody working here wants to make more money next year than they made this year.

Tim Cafferty:

I'm pretty sure of that. I haven't checked with everybody and I'm pretty sure. The only way we can do that is making sure we're billing properly for the work that we're doing, right. And when the season is upon us and those calls come in about the toilets clogged or whatever a billable scenario would be in your mindset, you insert issue here Do you have the billing process tight, that you are not only entering the work order for the work to be done but closing the work order and billing it? You do not want to be like I was a few years ago when I looked at the end of August and I found 700 open work orders, many of them from June and it's very difficult to go back to an owner and bill in August or September for something you did 90 days ago.

Tiffany Edwards:

Yeah, I hate to say we've been there too and really making sure that there's someone who does help go through some of those. We've put a little bit more on our accounting side during the peak season because they're right in front of the desk and maybe they can review a little bit more, but just making sure that those work orders are closed out, because those are really rough calls from an owner when they get charged over and over in November.

Tim Cafferty:

What else do you have for end season? Kind of things do we need to be thinking about as we are in the heat of the moment.

Tiffany Edwards:

So, in the heat of the moment, I still think it's important praise, check in with our team, which we've kind of talked about, but I also start planning out a end wrap-up party, goodbye to peak season. You did great so that our employees have something to look forward to and we try to make it really special something. If it's a bonfire on the beach in some locations, sometimes I'll bring in California, we'll do lunch and do a little party in the office, but something so that everyone feels touched, heard and celebrated and that there's almost an end in sight. And so we start prepping for that by sending things out and communicating with our team.

Tim Cafferty:

I love that that appreciation is not just the beginning of the season, the end of the season For those of you that are rental management company owners, your presence is a point of appreciation. I'll do a little self-brag here, or at least self-awareness here. For the last 20 years I have been the first one at work on Saturday morning. I come in at 5.30 on Saturday morning and I help the cleaners load their cars because they come here to get the materials to clean the houses. I ask about their children, I find out what's going on and first of all can't believe I'm actually the owner of the company. I'm just Tim, the warehouse guy who gets here early. Are you really the guy that signs my check? So that's really cool.

Tim Cafferty:

But then that weekly appreciation whether it's even cold water and snacks available to them when they come in, just a really appreciate a good job done there. And if you haven't made some sort of a brag board, ours is a big screen TV in the warehouse area where we can put those kudos up. There we get comments from guests. That's the cleanest house I've ever rented. You know, aaron got a shout out from the guest at SS1234, greatest house cleaning I've ever seen. Those go a long way.

Tiffany Edwards:

Absolutely.

Tiffany Edwards:

And I want to dive a little bit deeper, tim, because I also grew up where my mom was the dispatcher on Saturdays, where we used to have 300 check-ins in one day and it was seven days non-negotiable rental and my mom sat at the housekeeping office office and she'd sit on two phones and prior to when we had keys, prior to the locks, the electronic locks, we would know when a guest would leave, keys would be returned and I'd be at the front desk calling her to let her know to dispatch housekeeping.

Tiffany Edwards:

And then we'd have this constant communication of when guests came in to dispatch housekeeping. And then we have this constant communication of when guests came in. But to have the owner or the GM or whoever it may be in those offices, one, it's appreciation, but two, you get to see a whole nother level of your business and the efficiencies or inefficiencies, and that kind of brings us a little bit more to our post-season of how you evaluate. But you're never going to see the ground up than unless you are right there on a busy, busy day and you're ground level.

Tim Cafferty:

And, let's face it, there's a certain awareness you have as a company owner and an upper level manager. So, for instance, if I have Gloria who comes in as a housekeeper and just isn't looking just right for me, I've been known to write down what houses did Gloria do today and let me see how those turned out. And invariably Gloria is going to be a problem. You know, if they come to work dragging butt, they're probably not going to find energy on the way to the house. Maybe they cut a few corners, maybe they didn't do exactly what you're supposed to do and you've got to police that stuff, because in another episode we're going to talk about your brand and professionalism. Maybe two episodes actually, but at any rate it all fits together. I like to say everything speaks, and that speaks loudly when you see a one-off and you need to follow up on it.

Tiffany Edwards:

Or you've hired a company for contract services but you don't have the same cleaners week to week. So you know that the house isn't going to be consistent. But you now know why it's not consistent.

Tim Cafferty:

The other side of that, when you talk about appreciation and in-season, one of the things that I heard at a conference recently that I think we're going to implement is a bonus for staff that report consistently. We talked about call-outs earlier. How about somebody that doesn't call out? I use Gloria as a bad example. We use Gloria as a good example. Gloria reported to work every Saturday this summer and she gets to go in a drawing for an 85-inch big screen TV.

Tiffany Edwards:

It works, I'm telling you. I love that. That's great. I might be using that for some of our locations.

Tim Cafferty:

Use those credit card points to get some gifts that you can give away and bring it in a couple of weeks in advance so everybody can see the TV and they see that their name's in the hat. So that's good. So the postmortem, you can imagine we've already given you many things that you should be aware of. So how did it go when you do have a break in the season and understand? Over the last few years, many beach areas especially haven't had that break in the fall, but there does come a time where you can step back a little bit and see how it went.

Tim Cafferty:

How did our billing processes work and what do we need to change to make sure we don't have those work orders that are 95 days overdue, whether it be from our individual billing of our own people going out, or that air conditioner vendor that you were talking about, that you don't always use and they're not the best at accounting, and they forgot to bill you for that new unit. And so what kind of things do you put in place there? What kind of things did you learn from the season that you can put into place for a better season in the future?

Tiffany Edwards:

Tim I'll touch on that where some of those that we've done post-mortem, where we've learned one of it reviewing how many discounts did you give away and I know before we've talked about not talking through you know, using the word discounts, how many rebates did you give away instead of maybe offering a dinner or offering more towels or offering some other type of services?

Tiffany Edwards:

And so we learned that a while back, because I think a lot of our property managers would just be easy to say, well, let me give you some money back, instead of maybe providing a different service or just a listening ear. The other thing that we realized too we love, love, love Breezeway. We use it in all of our locations. We found that a lot of our tasks it would be open the drawer, look in the drawer, review the drawer, so it was taking way too much time to inspect a property. So we were getting to only a few in a day where we could have tripled and it was because there were too many tasks associated. So, really taking a look at where were some pain points where we can find efficiencies to earn or create more money and a better guest experience and a better experience for our employees.

Tim Cafferty:

If you aren't exactly sure what Tiffany was referring to there. Marco DiDimizio had his ears covered there for a moment when she said the word discount. Our previous podcast, where we had the king of hospitality on, said never provide a discount. Give them a guest loyalty, give them a credit towards a future stay. Those kinds of things work very, very well. That way you have also the second opportunity to earn that business back. Great strategies there. Okay, we've covered a lot here. Anything else on the post-mortem that you can think of that we should pass along to these folks.

Tiffany Edwards:

The only other thing I would say is really looking at when did you start your preparation for peak season, Because now in the postmortem, you have plenty of time to reassess. But create another action plan of when you should be looking at this.

Tim Cafferty:

And if you have a budget, go back and say well, I didn't put enough money in this line item. As we get prepared for budget season, which is gonna be about two weeks after the season for Tim's crew, we better make sure we remember that for the future. I hope you got something out of this today. Folks, we're both in the bros of the season, just like you are. I hope you prepared properly. I hope many of this doesn't resonate at all because you got it knocked, but maybe for a few of you you were able to jot down a few things that you can improve on and we are glad to help.

Tiffany Edwards:

And I can't wait. Next week, like you had mentioned, next episode we'll be touching a little bit more on brand, and all of this is hand in hand, because you got to build that brand loyalty, so this is the stairway to get you there.

Tim Cafferty:

So that's it for this edition of the Vacation Rental Key with TNT. We are so glad you're with us. Don't forget to send us a message. You can find us at our website. Spell it all out the Vacation Rental Key with T and T. Or you can find us on social media, which Tiffany's doing a great job putting out for you guys. We love to hear from you and, if you don't mind, look at that podcast app that you're using right now. There's an option up there for you to give us a review. We would love a five star review, if you can. Helps us get more listeners and helps us spread the word about being more professional in what we do and what we love.

Tiffany Edwards:

Thanks guys, Until next time.

Tim Cafferty:

So long, everybody, bye-bye.