A Booking Next Summer is a Mistake

September 30, 2025 00:13:21
A Booking Next Summer is a Mistake
Short Term Rental Management
A Booking Next Summer is a Mistake

Sep 30 2025 | 00:13:21

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Show Notes

On this week’s episode of Short Term Rental Management, Luke shares why booking too far in advance (like next Summer) could be a costly mistake for hosts. He dives into how the market is shifting, what platforms are rewarding right now, and the timing strategies that can make or break your calendar performance. Tune in to hear how Luke approaches pricing and availability to stay ahead of the competition.

 

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For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation PropertiesBuy it on Amazon

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Episode Transcript

[00:00:02] Speaker A: This is Short Term Rental Management, the. [00:00:05] Speaker B: Show that is all about short term. [00:00:07] Speaker A: Rental property management with your host, yours truly, Luke Carl. All right, Short Term shoppers, let's talk about our calendars. [00:00:22] Speaker B: My favorite subject, pricing. How do we get booked? [00:00:26] Speaker A: How do we put asses in the seats? Well, we're going to, of course we're going to need a rooftop mini pickleball court is the only way to get booked. [00:00:34] Speaker B: All right. I can't go 10 minutes without a pickleball court joke. Right? But anyway, here's, here's what's happening. [00:00:43] Speaker A: We are entering the fall. We're here already. We're in the fall and we are. [00:00:48] Speaker B: In a better interest rate environment. [00:00:51] Speaker A: Things are changing a little bit. Starting to get a little bit more exciting out there. We're actually seeing what is a healthy real estate market which we haven't seen in years 2020 and 2021. When everybody on and their sister's mom was buying a house for way over asking price. That was not healthy. Not healthy. What we have right now much more. [00:01:17] Speaker B: Closely resembles, much more closely resembles a. [00:01:23] Speaker A: Healthy real estate market nationwide. In the month of August, we saw 60 days median days on market nationwide. Now again, this is mostly primary homes because that's mostly what's out there and that's not what we talk about here at STRM. But 60 days on market, a healthy days on market is more like 30 days. [00:01:50] Speaker B: 30 to 45 days is very healthy. [00:01:52] Speaker A: We're getting closer. We're also going to start getting closer. [00:01:57] Speaker B: To some healthy inventory numbers. [00:01:58] Speaker A: So this is really what a good real estate market looks like. Much more so than 2021 when many. [00:02:12] Speaker B: Of you probably bought homes. [00:02:14] Speaker A: I mean, I know I did, you. [00:02:16] Speaker B: Know, and I got myself in trouble with a few apartment buildings in 21 also that I've already ditched. [00:02:21] Speaker A: But I also got some great deals. [00:02:22] Speaker B: In 21 in 2022. [00:02:26] Speaker A: But anyway, what we have right now is a much healthier environment. So that's very exciting as we move into the fall of the year. And then, and I also want to mention completely off topic, it is not too early to start thinking about Christmas in our lives in general. I love Christmas. It's coming. Let's get prepared. I've already scheduled some Christmas photos for the family. So long story short, this has me looking further ahead on my calendars and I noticed that I still have. I, I do this thing where I will block like basically a certain date. [00:03:02] Speaker B: On the calendar indefinitely. [00:03:05] Speaker A: And that usually means I just don't. [00:03:07] Speaker B: Want to deal with it like this. [00:03:09] Speaker A: Time of year, or I should say in the springtime of the year, you know, I'll have a, I'll have a 12 month, I'll have a 12 month. [00:03:17] Speaker B: Wind booking window on my, my platform, my OTAs. [00:03:20] Speaker A: But then I'll go on my management software and I will click and drag. [00:03:24] Speaker B: Starting on a certain date all the way indefinitely into the future on dates that honestly that I just don't want to deal with. And usually that means that in the. [00:03:33] Speaker A: Springtime. [00:03:36] Speaker B: I will, you know, click like. [00:03:38] Speaker A: March 1st of the next spring and. [00:03:42] Speaker B: Block it all off. [00:03:46] Speaker A: Because when it is April, I don't really want to deal with booking the next March, April, May, June, July. And also there's a lot of room for error and mistakes to be made. You also have to understand that if you have a 12 month calendar and today is June 1st, well, tomorrow, June 1st of next year will become open and available. And if you don't pay attention and get your pricing right, you're going to get booked for not enough money. So the reason I even thought about. [00:04:20] Speaker B: This is because I had one newer property. I have a new property that's been up for about a month now. And I noticed that it had, it was the only one that was not blocked March 1st moving forward. And I went to click it and. [00:04:30] Speaker A: Drag it and block it. And then I started thinking, wait a. [00:04:32] Speaker B: Minute, it's probably time to open some of these other ones up. [00:04:35] Speaker A: So now is the time to go ahead and look at next spring, decide how far in the future you want to be available. I still, I would argue that maybe June and July is maybe not ready. [00:04:45] Speaker B: To be available yet. [00:04:49] Speaker A: And that's a strategy. You're going to have to decide what you're comfortable with. But I think maybe March and April, it's time to probably open those up. [00:04:56] Speaker B: Because overall availability is good for your algorithms. [00:05:00] Speaker A: And now we're already sliding into October here. [00:05:03] Speaker B: And so if you do the math, hold on, I'm gonna count with my fingers. [00:05:07] Speaker A: October, November, December, January, February, March. It's not even, it's five, five months. [00:05:14] Speaker B: Cause March 1st, right? So at least in this example, so. [00:05:18] Speaker A: I only have five months of availability on my calendar. So there's boom. That's an instant algorithm boost if I. [00:05:23] Speaker B: Open up two or four or six. [00:05:25] Speaker A: More months on my calendar. Problem is, is it's time consuming. I'm gonna have to go through all my seasons. I do multiple seasons, right? So I basically have a base rate for every month. And I do that in my custom seasonal profile on price Labs. [00:05:42] Speaker B: If you want to know more about that, we'd lecture about it all the time on Short Term Shop Plus. We'd love to have you, but I do think that running with one base rate is kind of old school. We're beyond that at this point. You need multiple base rates and you do that as a custom seasonal profile and I would recommend you do one for every month basically. Obviously we could do two hours on that alone and I have done many hours on that subject in Short Term Shop plus. [00:06:09] Speaker C: This episode of the Short Term show is brought to you by the short term shop. 30 year fixed mortgages, tax benefits and long distance management training made easy are just a few of the perks of owning a short term rental. The Short Term Shop can help you buy and learn how to manage your property from anywhere in the world. Just go to theshortermshop.com and click get connected again. That's the shorttermshop.com and we are brokered by exp. See y' all over there. [00:06:36] Speaker A: Anyway, all I gotta do is open up, you know, March, April, May, probably. [00:06:40] Speaker B: Those three months is where I'm looking at right now. And then I've got quite a bit more availability, got a little algorithm boost. The world is happy. [00:06:49] Speaker A: Now. If we're going to open up June and July, that takes more effort and. [00:06:56] Speaker B: More work and you really gotta, you know, focus on your, your monthly base rates, your custom base rates, seasonal profiles. [00:07:05] Speaker A: Etc, and there's room for mistakes and error. Dare I say, and this is kind. [00:07:13] Speaker B: Of the entire point of today's program. [00:07:16] Speaker A: If you're getting a booking in June. [00:07:18] Speaker B: Right now, and early October, late September of 2025, if you're getting a booking. [00:07:25] Speaker A: In next June 2026, you priced it wrong. That's a mistake. So the first thing I see when I see a booking, if I see a booking come in today for next June, I say, oh crap, I made a mistake. Because there's snipers out there. They're out there trying to, they're sniping your, your pro, your calendar, trying to find like the cheapest dates and they. [00:07:48] Speaker B: Don'T know they're doing it. They're just looking for the best deal for whatever dates they're trying to travel. And some people are obsessed with it. [00:07:53] Speaker A: And trying to find deals. Listen, that should not be a foreign concept. There's a lot of people out there that are trying to find a deal. I'm pretty sure you were completely obsessed in trying to find a deal when you bought your vacation home. It's human Nature, especially for dudes, right. [00:08:13] Speaker B: To want to find a deal. So if you get a booking tomorrow. [00:08:19] Speaker A: For June of 2026, that was probably somebody looking for a deal and you probably got ripped off. So I see. That's when I cringe, when I see. [00:08:29] Speaker B: Folks on Facebook and. And they're like, oh, I've already got. [00:08:31] Speaker A: Three bookings in July of next year. I'm like, oh, whoa. Now, obviously it's market specific, right? There's certain markets where that's probably pretty normal, but where I'm at, it's not. I mean, it could be right. I think that a lot of property. [00:08:49] Speaker B: Management companies are booking next July and they're happy to do that. They're just filling up their calendar and. [00:08:55] Speaker A: But that's not how I roll. I'm still trying to book October, you know, and in my defense, that's why I haven't realized that my damn calendars. [00:09:04] Speaker B: Are blocked in March. [00:09:05] Speaker A: I'm too hyper focused on what's going on in the immediate future, which is what you should be doing, really. The, you know, the next three to four weeks is what you care about. [00:09:13] Speaker B: On your calendar in most cases. [00:09:17] Speaker A: But I had blinders on. And now all of a sudden, I. [00:09:20] Speaker B: Only have 5 weeks, 5 months available on my calendar. So I'm going to go ahead and get that opened up. And I'm grateful that I took a look at that. [00:09:25] Speaker A: And I. It took me like a day to realize that I needed to open this crap up. You know, I'm looking. [00:09:30] Speaker B: I'm sorry, man. [00:09:31] Speaker A: I gotta block off this new cal. My. This new property. The calendar's open in March. And then the next morning I was like, what? [00:09:36] Speaker B: Wait a minute. Block it off? [00:09:40] Speaker A: Why am I blocking it off? I need to open this stuff up and boost my algorithm. Let's get the availability going. Let's get popular. Let's be hip and cool, man. [00:09:50] Speaker B: Because that's how you get booked. [00:09:52] Speaker A: Great rates and popularity. So it's not too early to be looking at the spring and the summer. And if you get booked too far in advance, you priced it wrong in most cases. So in other words, what happens is if I see a booking come in. [00:10:09] Speaker B: Which again, I don't really look at all this stuff that much anymore. I have full time staff, which is wonderful. Which comes with scales, economies of scale. [00:10:18] Speaker A: It's wonderful. Takes time to get there. [00:10:20] Speaker B: All right, well, Luke doesn't even look at his messages anymore. [00:10:24] Speaker A: Yeah, because I've been doing this for how many years and I worked my rear end off and I. My My time is better spent elsewhere, like acquiring new properties, rehabs, constant rehabs. [00:10:42] Speaker B: Anyway. [00:10:46] Speaker A: Let'S just say a booking comes in and it's got a seven in front of it. You know, July. I'm like, oh, I'm cringing. Oh, my God, I got booked next July. Oh, this is not good. Somebody booked my 4th of July for too little money and. Or something like that. And, and then I go look at it and it's like a crapshoot. It's like, oh, man, I got like a 10 chance that this is a. [00:11:06] Speaker B: Good booking because it's possible that I. [00:11:08] Speaker A: Priced it too low. Otherwise why would they be booking it so so far in advance? And then I look at it and then it's like, oh, sweet, Price was right. [00:11:15] Speaker B: I'll take that one. And then you still second guess yourself and you say, oh, man, maybe I could have gotten a little bit more money for that. You know, it's kind of funny how that works. [00:11:29] Speaker A: So if you do get booked six months or more in advance, you probably priced it wrong. General rule of thumb, that's point number. [00:11:44] Speaker B: One from today's program. [00:11:45] Speaker A: Number two, we are in the. Going into October of 2025, it's time to go ahead and get spring open and keep the prices a little bit high for those dates, but it's probably best to go ahead and get them open at a price that you're willing to book them for this far in advance. June and July, I still think it's okay to have those blocked off if you don't want to deal with them yet. [00:12:08] Speaker B: Especially if you're on the beach, you're. [00:12:11] Speaker A: Going to make the bulk. [00:12:12] Speaker B: I mean, you're going to make a very large percentage of your gross annual income in the month of June and July on a beach house. And as we are moving into the holidays and things like that, do you really want to be letting your June and July fill up while you're so busy you can't even think about it? And the next thing you know, they were booked way too low, and then you blew your whole year. You know, it can be done. [00:12:39] Speaker A: If you're going to have June and July open, put them high. [00:12:42] Speaker B: Like, pretty damn high, okay? [00:12:47] Speaker A: And that's it. Get those calendars open. Pay attention. We're fall. We're, we're. [00:12:53] Speaker B: We're flowing into the holidays, man. [00:12:55] Speaker A: So springtime, it's right around the corner. You got to be thinking six months. [00:12:59] Speaker B: Ahead in this business. [00:13:00] Speaker A: I love you, Cash flow. Carl saying, don't overthink it.

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