Does it sound familiar to struggle with increasing your direct booking rates? You’ve probably been told to rely solely on online travel agencies (OTAs) for bookings, but this has only resulted in high commission fees and limited control over your property. This can be frustrating and costly, leading to decreased revenue and a lack of control over your property’s success. It’s time to break free from this cycle and take charge of your direct booking rates to unlock higher revenue and greater control over your property.

If it has a picture of a pool, well, it should have a pool when they show up. It really should deliver what you say you’re going to deliver and then give them a good experience while they’re here. – Chris Walker

In this episode, you will be able to:

My special guest for this episode is Chris Walker.

With over 15 years of experience in the vacation rental industry, Chris Walker brings a wealth of knowledge and expertise to the table. His journey from a culinary background to real estate and property management has equipped him with a unique understanding of guest satisfaction and direct booking strategies. As the partner and CEO of Booking Insights, Chris has been instrumental in developing innovative solutions to help property managers display the best prices on their websites and increase their direct booking rates. His insights into the psychology of guests and the impact of website conversion rates make him a valuable resource for property managers looking to elevate their direct booking success.


LinkedIn: https://www.linkedin.com/in/chriswalkerhhi/

Website: https://www.directbookingtools.com/

Mention the DBS Podcast and get a 45 days extended no commitment free trial

The key moments in this episode are:

00:00:08 – Introduction to Short-term Rentals and Hospitality Industry

00:00:36 – Transition into Short-term Rentals

00:03:27 – Introduction to Booking Insights and Direct Booking Tool

00:09:03 – Understanding Website Conversion Rate

00:12:22 – The Billboard Effect and Industry Evolution

00:13:57 – Importance of Keeping Visitors on Your Site

00:15:51 – Managing OTA Pricing and Anomalies

00:17:43 – The Value of Direct Bookings

00:20:10 – Importance of Customer Service

00:22:01 – Special Offer and Testimonials

FREE GUIDE: 10 Ways to Drive Guests to your Website instead of Airbnb: https://directbookingsuccess.com/10-ways-to-drive-guests-to-your-website-instead-of-airbnb/

Show notes are available at: https://directbookingsuccess.com/podcast/

Follow Jenn on Instagram: https://www.instagram.com/directbookingsuccess

Join Jenn’s free group – the Marketing Hub Free Facebook Group: https://www.facebook.com/groups/marketinghubforholidayrentals


00:00:32 - Jenn Boyles

Hello and welcome to another episode of the direct booking success podcast. I'm Jennn Boyles, your host, and today I have Chris Walker with me. He is the partner and CEO of booking Insights. Welcome, Chris.

00:00:46 - Chris Walker

Hi, Jenn. Thanks for having me. It's good to see you.

00:00:48 - Jenn Boyles

It's good to see you, too. Let's start with maybe telling us a bit about how you got into the crazy world of short term rentals.

00:00:56 - Chris Walker

Yeah, it's been a while. I'm actually from a culinary background. I went to culinary school, was in that industry for 18 years, and I got out and started selling real estate in three. I figured if I could make brides happy with food and beverage, I could make them happy buying our homes. I made the transition into real estate so I could get my life back. Interesting enough that has gone in a different direction as far as time, but that's okay. Then at seven, we decided to start a property management company because we were selling high end resort properties here on Hilton Head island. And it was just a natural progression because people kept asking us if we would manage their properties. And so we got into the business at seven and we've been in it ever since. So 1516 years now we have the vacation rental business.

00:01:43 - Jenn Boyles

And you were a chef in hospitality. So in hotels, weren't you?

00:01:47 - Chris Walker

Hotels and resorts, yes.

00:01:50 - Jenn Boyles

Right. Yeah. So it is. You sort of went off into real estate a bit and then right back into hospitality. But combining that real estate.

00:01:58 - Chris Walker

Yeah. The food and beverage industry taught me very well how to multitask. We ran big operations of 200 employees, $10 million a year. It's a big operation, so it's a lot of juggling of things. That's what we do in the vacation rental industry. There's no doubt about it.

00:02:16 - Jenn Boyles

Definitely. And I can see the progression, too, of selling the homes and then people going, okay, well, now I have it. I need somebody to manage it for me. And being able to step in there, too, seeing that hole in the market.

00:02:31 - Chris Walker

We do. Yeah, we actually oversee interior design and remodeling. So they come in, they buy it, they leave, they come back, it's completely redone. And we put it out on the vacation rental market. Handle that for them. So it's a seamless process for the clientele here on Hilton Head.

00:02:46 - Jenn Boyles

Oh, wow. I love that idea. The one stop shop it is. That's great. And then booking insights. Okay, so how did this come about?

00:02:56 - Chris Walker

Well, as if we didn't have enough going on, my partner with the website developments and things and advertising and marketing, Josh Zatmari. We've been partners for 15 years working in the industry together. We just came up with some ideas that we thought that could help people in the industry. And we've got a lot of products in mind. And the first one that we've rolled out is the direct booking tool, which lives on your website. We thought it was the easiest install, easiest uplift and most impactful product we could introduce out of the gate and impact it has had, that's for sure.

00:03:27 - Jenn Boyles

Yeah. No, and it looks really great. And I can see, yeah, you've got enough on your plate. Why did you decide to start something new? But again, it's that gap in the market, isn't it? You could see a product that would help.

00:03:40 - Chris Walker

That's right. We love helping people and we love doing the right thing. And this is well on that way. I mean, this is right up that alley. This fits it perfectly.

00:03:50 - Jenn Boyles

So let's talk about it. So it is the booking insights direct booking tool. Can you tell us a little bit about how it works?

00:03:59 - Chris Walker

Sure. Yeah. It's a script that lives on the property manager's website. This is not some loan website type thing. This lives on your website. Every time a guest goes to your website and does a search and they go to a property page and they've got a set of dates in and you on your booking page have your pricing there, we go out and we find the matching OTA pricing and we deliver that to that page for that guest when they're on your website. So when they're there and they see that the price for your stay in your property is, say, $5,000, well, it's probably going to be 5800 on Vrbo and 6500 on Airbnb. Whatever those numbers are. That's what we produce and show them. So that it's a true price comparison for the vacation rental guests to see that they're in the right spot, it gives them the confidence that they're in the right spot for the best price. Therefore, they obviously make the buying decision.

00:04:54 - Jenn Boyles

Because that's one of our big selling points, isn't it? For book direct, you're going to get the best price if you go direct. So this is showing people right there and then if you go the same property on Airbnb booking.com Verbo, this is what you would pay if you book direct. This is how much you're going to pay and how much you're going to.

00:05:15 - Chris Walker

In starting this wasn't, I didn't realize this. A lot of these metrics that I know today, I didn't know back then, and a lot of companies don't understand the metrics behind some of this stuff because they're busy running their companies. And I totally understand that. I myself didn't realize that the public perception was 85% of the public perceives the Otas to have the best price, even though never mentioned pricing in any of their advertising. But the perception is there because they spend billions of dollars or have spent billions of dollars in marketing this segment of vacation or of travel. And we're here, we're supporters of them. We think they're good advocates to have in the market because they certainly have brought a lot of attention to our sector in the market and have helped us all grow in inventory. More and more people have fluctuated or followed this sector of travel and that's a great thing. But the truth is they do not have the best price and that's why they never mention pricing in their marketing.

00:06:10 - Jenn Boyles

Yes. And I think right now we're seeing Airbnb. When they started it was all about get those cleaning fees in there and now they're realizing that it is very off putting when you put in your dates and you see a completely different price than the, what you were promised at the beginning, which is something we've always done on most book direct websites, direct booking websites is just give them that final price. Don't add all these things into it. So I love that we were leading the way in the know and Airbnb is seeing this and.

00:06:53 - Chris Walker

People today, especially after this, know that everybody's dealt with the economy of everything getting more and more expensive. Everybody is looking to save a dollar wherever they can today. And when they can see that, they can save 500, 800 or even $1,500 by booking direct with the property manager. That trust factor goes way up because a lot of times, I get it, you got companies that only have four or five properties or ten properties. They don't have a lot of reviews and that kind of thing. There's that question of trust. But when you show them they can save $500, the trust value goes up real high real quick.

00:07:27 - Jenn Boyles

Yeah, I think it does. There's definitely a lot of things we can put into our website to help build that trust. But prices, it's like, put your money where your mouth is, right? Absolutely. Having those prices right there on the website. Is there anything in the psychology of the guests that will help them book?

00:07:47 - Chris Walker

Well, you talk about all the information that we try to pack onto our websites and tell them how great we are and we're sincere about that, and we show them the reviews, we talk about how we have the best price guarantee. Nobody trusts anyone anymore because everybody's getting a little side hustled here and there. Wherever they go, whatever they're buying, they feel like they're getting hustled. And so when you actually show them the facts and you deliver those facts in front of them, you've just captured that trust and you've captured that client. Because if you have what they're looking for, for the dates that they're looking for, they're going to stay there and book with you. They. Absolutely.

00:08:24 - Jenn Boyles

Now, I started my journey in helping others in the short term rental space by creating sort of how I started, but I quickly realized that I was giving people these websites and then they were going, I don't know what to do with them. How come people aren't just booking, thinking if you build it, they will come mentality. And I think something you touched on a few minutes ago were the metrics behind your website. And I wanted to dive into that a bit because I don't think a lot of people understand that looking at your website and knowing how it should be performing. Can we start with the website conversion rate? Maybe talk a little bit about that?

00:09:05 - Chris Walker

Absolutely. And same thing here. I had no idea what my website conversion rate was. No clue. In fact, I was shocked when I found out what that number was. Industry wide, believe it or not, its zero point 52% is the conversion rate of a vacation rental website. That means you need 200 people to come to your site and look around for you to get one booking. Mine was at zero point 32%. So I needed 300 people to come to my site. I had no idea. And I had all these people come to my site. I put this product on my website and I went to a 1.2% conversion rate. Now I only need 85 people to make a booking. So that tells you right there that the product does work on. And the convincing proposition, because I didn't change anything else in my marketing, my metrics or anything else, is that people just need to see and understand that what you're truly offering is the lowest price in the market. And so that conversion rate, I encourage everyone to go out and figure out what that conversion rate is on their website, because small or large companies should know that, because you need to know how many eyeballs are hitting your site in order for you to get one reservation. Okay. And if you can increase that exponentially, then you're winning. Right. You don't have to spend as much on marketing and that kind of thing. So as a smaller player in the market, you might wonder, well, how do I get those eyeballs to my site? Well, you do that through what we call the billboard effect, and that's through how you set up your OTA listings to begin with. And I've got a few metrics there, if I may. Yes, please.

00:10:40 - Jenn Boyles

And explain what the billboard effect is. I use the word sign posting, but it's the same thing. But do explain it.

00:10:46 - Chris Walker

Yeah, very good. Same thing. Same thing. So the billboard effect or sign posting has a lot to do with consistency, making sure that your headings on your otas are the same heading you have on your website. So if it's one, two, three main street, make sure it says one, two, three main street on all the sites. If you have a picture of the pool as the main picture of the property, then make sure that main picture of the pool is the same picture on all the otas and your main website, make sure that you have it listed by your company, not just your name, because people want to know that it's a company they're dealing with. Put your logo on there and then also put your name hosted by Jenn Boyles at Happy Holiday Homes. Okay. That type of thing. So you have the personal touch, but at the same time you have the company name. People are becoming more and more savvy to where they'll be able to find things. They can even right click. A lot of people don't know this. You can right click on the picture, the main picture, and say, search Google for this picture and your website's going to come up. Or they could just go, one, two, three main street, you know, Jennn Boyles happy holiday homes, and you're going to come up number one in the search engine. So there are people finding, they're curious, they're wondering if they can find a better deal.

00:12:02 - Jenn Boyles

And I think more and more people are understanding the benefits of booking direct. And more and more people are using tools like Google to find the direct booking websites from a listing.

00:12:15 - Chris Walker

Yeah. The industry is fairly new, right? Especially technology wise. It's the new year 2025. Right. It's been in the works for more than 35, 40 years. But you've had some bad apples in the industry that cause some people to not really trust vacation rental managers and one off scenarios that give people a bad flavor in their mouth about booking with property managers. But we've come a long way as an industry and we continue to make great strides in that direction of bringing real respect to the industry. And I think a lot of us are doing a very good job with that.

00:12:50 - Jenn Boyles

I totally agree, and I love that you've brought up the website conversion rate and people get these websites and they say, okay, well, now how do I get people on it? And that is actually harder than putting your website together. It's getting that traffic and that consistent traffic. So the billboard effect or sign posting, whatever you want to call it, even if you have just the one property, will help people to come over. There are many other ways that you can use to get your traffic up. I have a guide, I'll put a link to it on the show notes here. If anybody wants to get that. It's all about getting your traffic to your website instead of people going to Airbnb. One thing that I see people do, and this is another reason why I really like your product, is I'll see people on their website have the booking.com or the Airbnb logo on the website or their super host status, right? And I'm like, no, don't do that. Because people will then go to those places with good intentions to check you out, but then they'll get lost. They get lost.

00:14:07 - Chris Walker

They're gone back. Yeah, the shiny little object shines. The next house shows up, they go to that house and you're lost. You're gone. You never want to send people away from your site. We've even had people ask if we can link our price comparisons to those otas to verify it. I'm like, no, you don't want people to leave your site. Now, if they take the intuition to go check it, they can go check it if they'd like. It's down to the dollar that it's accurate. But you don't ever want to have people leave your site.

00:14:39 - Jenn Boyles

No. And that's enough to get them. It's a big trap that I see a lot of people fall into because they're like, well, I want to build that trust. I want to show that I'm on these other platforms, that I am who I say I am. And I'm like, well, that's not the way to do it. Not at all. So that's why I love your product, because you're doing the trust saying, yes, I'm listed in all these other places, but then you go that one step further with the price. And my question, I know when we first met and we talked about this, I said, okay, this sounds all great. And oh, I love it. Except there's one platform out there that will discount guests for breathing and they like to go, and sometimes you'll get an email, somebody has booked your place and you're just crossing your fingers hoping that it's a decent rate because who I'm talking about is booking.com. And they love to discount. Now, it's a platform I use when I'm traveling because I know that they're going to discount and discount and discount. However, as a host, as an owner, as a manager, it's a really nail biting effect of what rate they are going to use. So tell me what you are doing behind the scenes just in case there is a discount that they're putting on there that will bring you below your direct booking rate. What, on your end?

00:16:03 - Chris Walker

Yeah, it does happen. And actually we help the property managers maintain to make sure they are distributing their pricing correctly across the OTAs. So if it ever shows up equal to or less than your own direct booking price, it'll eliminate the OTA and just shrink the product down to the remaining direct book price. And the one OTA or two otas you've got left that are higher price. So we don't ever want to throw the property manager under the bus, if you will. But besides that, we also have a data dashboard on the back end that actually tracks this information and will show you where those anomalies are happening, whether you are aware of them or not. You might be aware of them. You might be running some ads or specials on the OTAs, and that's fine. You do what you have to do to get your business. But we show you on the back end where those price anomalies are so that you're aware of it, so that you don't end up with a reservation that's supposed to be $5,000 and it comes in at 4500. And then you gotta pay the OTA a commission and do all this other stuff and you're really out of pocket. That can really, that can really hurt you in a lot of ways because going back to them and saying, well, I'm not going to accept this, well, that doesn't do you any good these days either. That'll hurt you in the long run as far as your rankings as well. So I mean, again, you want the OTAs, you want to play ball with them, but at the same time, you want to be in control of your own destiny with your direct bookings. And anywhere from 60% to 70% is where you should be and even higher if you can get there. But, I mean, having a small margin of OTAs in your mix is not a bad thing. Bring fresh people into your fold, and that's okay. But you need to lead the charge of your own business and be in control. That's for sure.

00:17:44 - Jenn Boyles

I agree 100%. Yeah. Very much aligned in our thinking here. And I think that's great that you've got the property manager's back. So if that price is dipping, hey, let's talk about it. Let's get that fixed. But also, the tool doesn't lie. No, it's being very transparent. It just lets that one just slip off for the time being, which I think is a great selling point for it. Really well, yeah.

00:18:15 - Chris Walker

And we find a lot of times it's not intentional. It's not because of discounting. It's because they've made clerical errors or punch code errors into their system, and it's just not distributing to the OTA correctly.

00:18:25 - Jenn Boyles


00:18:27 - Chris Walker

We want them to know, be aware of them. A lot of people are very appreciative of that because we also send them a weekly report of those types of things that are happening on their website as well.

00:18:36 - Jenn Boyles

Yeah, because we've all made those mistakes. We've all made that pricing mistake, or our calendar was open too far in advance and we haven't updated prices. We've all had that booking come in, and we've gone, oh, boy, I've made a mistake. But of course, we honor it and we deal with it. But there you go. Yeah, it can be quite annoying.

00:19:02 - Chris Walker

The other thing, too, that I'd bring up is talking about the OTAs and how they're capturing it. I thought about it the other day, and I'm like, 25 years ago, before the advent of the Internet and everything, all vacation rental companies were 100% direct booking because that was the only way you went then. We talked to so many people today that their direct booking mix is anywhere from 15% to 25%. It's very common that they have lost that much ground in what they're doing and how they're operating in that they need to get back on top and be in control of their business. Those OTAs are selling them travel insurance and damage insurance. When they book direct with you, you can sell them travel insurance and damage insurance. So that's ancillary income directly to you. So, I mean, the direct bookings are much more valuable and they'll come back to see you time and time again as well.

00:19:54 - Jenn Boyles

Yes. If you're doing it right, if you've got a kick ass guest experience and they're the right fit for your properties, then yes, they'll be back over and over again. And that's how you win at the direct booking game, isn't it?

00:20:09 - Chris Walker

It is. Customer service is number one, that's for sure. Provide the product you say you're going to provide and then back that product up with proper service for sure. And that's all people want, really. Nobody's looking for anything more than that. If it has a picture of a pool, well, it should have a pool when they show up. Right. It really should deliver what you say you're going to deliver and then give them a good experience while they're here. Should they have any issues or problems, be progressive, get on top of it and be reactive.

00:20:42 - Jenn Boyles

And the great thing about being direct is that they don't have to go through a middle person to reach you. They can just get in contact with you and you can have the chance to fix it, because a lot of time, it's not the problem that's the issue, it's how you react to it.

00:20:58 - Chris Walker

That's right. Absolutely. Anything can be fixed and it should be. And your timing on it can increase or decrease the severity of that problem. Very much so if you choose to ignore it, things get worse.

00:21:13 - Jenn Boyles

Yes, definitely.

00:21:14 - Chris Walker

For sure.

00:21:15 - Jenn Boyles

Can I ask you, what does direct booking success mean to you?

00:21:19 - Chris Walker

Direct booking success mean to me? To me, it's having happy guests and happy customers that are leaving great reviews and coming back year after year with their families and watching them grow year after year and just really almost becoming an extension of your own family, because people enjoy the products that you deliver and the services you provide, and it's just a great thing to see that happen when that does happen. So we're happy to see that for sure.

00:21:47 - Jenn Boyles

Great. And I'm going to put links to your website and also links to your LinkedIn profile. If anybody wants to get in touch with you, get connected with you. And you want to extend a special offer, don't you, to listeners?

00:22:01 - Chris Walker

Yeah, absolutely. We offer a 30 day free trial. We'd love for people to try the product out and make sure it's what they like. And then it's month to month after that. There's no long term contracts for anybody who mentions this podcast, we'll extend that to 45 days for them. We'd love to try it out. Have you try it out, take a look at it, see how it can affect your business. And we've not lost a single client yet. We've got about 90 clients plus on the platform today, and we're excited about that. We love what we're hearing from our clients and look forward to others joining us.

00:22:33 - Jenn Boyles

Yeah. And watching their direct bookings increase.

00:22:37 - Chris Walker

Yes, and it does. My own direct bookings went from 23% to 65%.

00:22:43 - Jenn Boyles


00:22:44 - Chris Walker

That is a massive change. And a lot of other companies are seeing that kind of a lift as well. It works, and it's not hard to install. It literally takes about ten minutes of the property manager's time to get going. Yeah.

00:22:56 - Jenn Boyles

And I'm sure you'll walk them through if you have any problems.

00:23:00 - Chris Walker


00:23:01 - Jenn Boyles

Yeah. Well, that's great. Well, thank you so much, Chris, for coming on today. I've really enjoyed our conversation.

00:23:08 - Chris Walker

Thank you, Jenn. I appreciate it.

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