Winter Checklist for Airbnb Hosts

YouTube video (hosted by Mark Simpson) auditing an Auckland host’s (Hannah / Hipstay) Airbnb listings, website and socials to improve winter bookings. Covers practical changes: seasonal photo shoots and titles/descriptions tailored to winter, rebranding/listing naming convention, website redesign (direct-booking funnel and separate property-management landing page), lead magnets/email capture, Instagram content strategy, and specific copy/photography directions and examples.
Chapters
Have you ever noticed how your bookings vanish the moment that winter hits? Hannah from Hipstate, who's based in Auckland, New Zealand, was facing the exactly the same issue. But I audited her listings, socials and website with the Boostly GPT and there's now a clear path forward. So in this video I'm going to show you exactly how she and you can easily position your listings, sharpen your photos, create compelling lead magnets and and win steady bookings through any season. And if you would like me to roast your marketing on a future video, click on the link in the description below. Let's roast. Let's do this. So as you can see here, we've got Hannah from downloading it. Do go and check him out again, they are not sponsoring this. I just a massive fan of the product. So we go and look there and as you can see here, we've got a couple of listings, all that good stuff and we've got this. So really well photography, you know, really well done, really well put. But as you can see here, the first bit of advanced settings give is that if Hannah, if you are struggling for bookings during the winter months, then we need to start having two different seasonalities for your Airbnb listing and for your website photography. Because at the moment this speaks to spring and summer. I can pretty much guarantee now without doing any major research on this or asking you, but if you want, you won't have two seasonality pictures. So what you need to be doing is you need to be, if you want to be getting bookings for. And I can see here, this is pretty empty. June, July, August. Obviously there are going to be travelers going to Auckland in June, July, August. It's not like it just goes like, like in Dubai where just nobody visits. Obviously people are still going to be traveling through, but you need to make sure that your listing stands out for it. So let's have a little look at this. So we're gonna. We'll take this one as a prime example just because I know you've got a few, but they all follow this. Absolutely the same vibe. But I'm going to take this and just like I did on the last one, another free Google Chrome extension that we use is go full page. You click on that and what it's going to do is it's going to take a picture of the whole of the site. You click download and we'll come back into our GPT here that I've been working with alongside the one on our site and we're going to go here and we can also go to here as well. So rewrite the title based off getting more winter bookings. So we're going to do that on the site there. So again you can either use the free one booster.co.uk bot my digital twin or you can go ahead and use it on your own version of GPT. So versions that it's come back with cozy rental retreat, park views, Netflix free bikes, washer and dryer, cozy city stay with netflix bikes, heated comfort and parked views, warm and stylish retreat, free bikes, cozy couch, fast wifi, winter ready apartment, park views, Netflix bike and comfort. So as you can see here already from the title, it's speaking to what you want to get across now with the pictures instead of having these light bright ones, what you want to make sure is that it looks a little bit more wintry. Okay so for example, you could have on here or whatever it would be for winter in Auckland. Again I'm not entirely sure but it could be some more froze on there. It could be mug of hot chocolate, whatever. You associate more with that. So let's go in and just go and ask again a little chat GPT here, come into here, come into here. What amendments would you do with the photos here to give it more of a winter vibe? Give directions for the photographer. Now obviously you're gonna have to do a new shoot, obviously. But. So warm and soft. Switch off any harsh overhead lights, use warm bulbs in the lamps, shoot during golden hour, prioritize warm diffuse light, stay for winter blankets and froze cushions, hot drink scenes, books and candles, Netflix ready. Place the TV remote and fully throw in the couch as a set of movie night cozy reading by the corner. Watch all that good stuff for sort of, for sort of winterness, winter ness. Because at the moment this does look spring. It looks sunny outsideness and all that good stuff. I definitely agree that the free bikes is a good is a good one. I did have a little ask of a couple of questions about the type of avatar that you would have come into the coming to the area and I definitely feel like you know from looking at the website and for looking at where people are coming from, it's a nice combination of people from New Zealand, people from Australia, but you do have people from obviously America that have left reviews and you have also got people from the uk so it shows that it's an international market for sure People you know do. They do love it, you know. And what I would be looking to do as well if I was to go back to maybe July of 2024. So an event which is very good. So Hannah's little man was really lovely. The only downside when you could ideal location. So again, it's a city stay, right? This is literally what we're, what we're looking at here. So yeah, basically what I would be looking to do here, number one, would be change your pictures and change the title and change your, your wording as well to speak more to the winter. What is happening in the winter? Why should they stay with you in the winter? Because again, at the moment it looks very bright, it looks very cheerfully. It looks spring and summer. You need another photo shoot for your autumn and your winter. And again, style it with, you know, hot chocolate on there, bit of a moodier sort of scene, maybe a nighttime one that's got, you know, Netflix on there so people can understand. It's Netflix. Netflix and chill and all that good stuff. But that's the first thing that, that you would definitely need to be doing and you can follow that theme through here. So you wouldn't be showing this pool shot in the winter time because unless it is heated, you're not gonna have anybody going in there for the spring and Summer 100. You want to be talking about the, the pool, right? Because obviously that is a big, a big selling point. And then again, free car park. So keep the car park pull. Partner. Partner few. So it does say hot tub. So again, I'd be maybe taking this and what we would do with this one, you would say about instead of pull, which sounds cold, which sounds summery, you advance hot tub. So. Now amend this for a winter stay title and description and photo advice. So again, I'm going to share all of this with you, Hannah. Don't, don't worry about that. I will definitely share that with you because you'll get it all in your email afterwards as a thank you for doing this. But yeah, I feel like the main feedback would be for your listings would be to go through, go and give them a bit of a spruce up. But also as well, what you need to be doing in the first line of every single one of this is you need to be giving it a bit of a, a bit of a name. So give your building and give your apartment a branding name and then also always mention hipstay. So for example, to say this is Park View brought to you by Hipstay Auckland. Okay? Because every single time you're doing it, you are billboarding that your business is hipster. You do it so well in your profile. Hipster but you need to do it on each individual one of your listings. So let's just say, for example, this is Park View or brought to you by Hipstay Auckland. This one. Then this next one would be, this is Sky Tower, brought to you by Hipstay Auckland. So it professionalizes the brand, professionalizes the business, professionalizes the listing. And again, people will then associate you with not just being on Airbnb, but you being the business, which is Hipstay. So for this one, for example, again, this, this screams spring and summer. It needs to be looking a lot more for winter. But this one, let's just say this is. This is King Bed, brought to you by Hipstay. Okay, Ashley, let's go and ask our trustee chat GPT. So we're going to save this. Come on to here, upload this file. I need to brand this house based on what you read, give it a branded name. Let's see what it comes back with. And again, the cool thing about this is that instead of just hitting copy all and copy paste, it's actually taken a screenshot of the whole page. It's reading absolutely everything, including all of these reviews. So it's taken all of that information to heart and to hand when it does do it. So this one, the one that we were just on, that I struggled with a name for this entire rental unit, it's come back and said Parkside Oasis Retreat. So this is Parkside Oasis Retreat brought to you by Hipstay, which is pretty cool. So do that on all of those. Again, you need new pictures for all of them, new title for all of them. So you've only got four. So this could be literally less than 30 minutes to rename it. The picture is obviously going to take a lot of time, but the good news is, looking at it, you haven't got a lot of availability. So you can easily get in organized with a photographer. You don't have to do all four at once because obviously you've got four spread around Auckland, but you can definitely go in one by one and rebook them. Rebook them in new pictures, new title, new description to speak to winter. And then obviously, as you start getting out of winter, you start coming back into spring, you just flip them back to these, which will. Which will be really, really good. And you can tell how they're working by your stats on the back end of your Airbnb account. Okay, so that's super simple for there. Let's go have a look at the website. So again, you are using hospitable for your pms. By the look of that logo here, you've got your website right? Now obviously you want to get bookings. First and foremost you need to get bookings, tap into the many, many people. The thousands of people will be on Airbnb on a daily basis looking at Auckland. But the end goal of this, obviously you've been doing this for eight years now. You want to start to be building your diary booking business and there is nowhere in here, but it looks to me that you're starting to do it. And I can tell that because the website, the website, as you can see on the screen, is not very good at all. It's, it's very old fashioned, it's very out of date and it needs a spruce up. So what we're going to do next is we're going to take this site and again we're going to take a little screenshot of it and what we want to do is we want to be able to speak to the user again, very simple with the website. Who you are, what you do. How can I buy from you now? It's easy how to know to buy from you because there's a book now button which is great, but there's definitely so many things that are, that are missing here. So we're going to come in to our trusty GPT here, Just going to save this again, going to upload it. I would like for you to design me a better headline and tag line for this website because what we're going to do is we're gonna, we're going to move it over to a boostly framework of a site. So this is obviously the boostly framework. We've shown this before. This actually springs screams Winter 100. I know you haven't got this view, but again, let's just, let's just use it for this example. That's not there. That's not the right one. I want to come into here. There you go. Okay. Okay. Well, it's doing that. Your cozy winter escape in Auckland. Hot tub nights, park views and winter comfort boutique. Comfort meets winter calm. I like that. So let me just whack this in here. I'm not entirely sure on the one that it's giving me there. I want to see for the, for the whole hipster brand, see what it comes up with. Because the website at the moment, like I say, this is the very old school style of doing this. This is like the olden way. We want to put this into like more of a new style. Your local cozy stay in the Heart of Auckland. I like that. So we're going to move that. We'll bring that over to here. Your cozy local stay in the heart of Auckland. Tagline, thoughtful design. Apartments with comfort, character. Just steps away from the city parks and culture. I do like that. See how that works on there. So obviously you have the fire in the background. You can add your image to it. But your cozy, local stay in the heart of Auckland, five star vacations. So arrival, departure, guests, nice big image in the background. Your hipstay logo will sit up instead of being front and center. It will sit in the top corner here. Homes, experiences, services. So services that you have. So your services are more your management model. We'll talk about that in a second. I don't see anywhere where it's talking about local experiences. I can see a blog, but we need to talk about local experiences. So you've got a real cool thing here on vintage shops. We can definitely come back to there. But if we're going to redesign the site, homes will be the four homes that you've got. Experiences. Now that Airbnb are literally talking about this more, you can have an experiences page on your website that you either hand in, put them in yourself, for example, you've got here talking about places to go, shops to visit. Great. But what would also work well in there would be Viator. So you can have a Viator listings that will go in there. You link it up to a Viator account, it's free to set up and then you'll get a little commission if anybody books a tour or an experience. Again, you don't get that on Airbnb, but you can get it on your direct booking site. And services. Again, you can have anybody in. In Auckland that offer these services. I think you've got to match up to your vibe, but I think your vibe is very much yogary, you know. You know, imagine like having yoga or photography, private chefs, etc, you can have that. Create your own, put it on someone like the Host Co. Again, a free online shop, you can do it yourself with a blog. But again, having that onto the site, this is what people are expecting now because Airbnb have created these categories. So be great to have on on your site. And I think that would look a whole lot better with a nice new image here. Let's see if I can actually go and show it based on one of the ones you've got. Let me go and pick one. Let me just take this. I don't know if I'll be able to do it because it's obviously, I'm taking a screenshot here and obviously you're going to get your own pictures done, you're going to get new pictures. But let me just take this, see if this works again, because I'm taking a screenshot and I'm not using the full version. This isn't going to look as good as what it would be. Take on the video for a sec. I'm going to change over the image, I'm going to upload an image, but this is just to give you a bit of a visual of what it would look like. Okay. Yeah. So as you can see, that looks a whole lot better. And again, you can do some cool stuff and literally I'm doing this now, but you can do a whole lot of cool stuff with the style on this. Add a little bit of a text shadow onto the background so that it stands out a little bit more and all that good stuff. But again, this is just me having a little play. This is what the Boostly designers. Whoa. This is what the Boostly designers do. Where's your style? Decorative transform, letter spacing, word spacing. All that good stuff takes shadow. That's the one I want. There you go. Anyway, you can have a lot of fun with that when you get going. But again, that looks a whole lot better than the one that you've. You've got here. Now let's very quickly talk about something that I noticed on your site, which was services. Now, you do have a management model. So obviously you want to get in front of homeowners and you want to take. Take their property and put it under your management model. As long as it fits into your vibe, which is totally cool, all that is good. But what I would be looking to do for you is I wouldn't be doing that on the top here. What I would be personally looking to do now would be having a separate site, but would be to talk about your management services. Because you want to have a clear site that is around here, but you want to have a landing page talking about the management services. Just to show you an example of one, I've come into the Boostly, the Boostly CRM. So all Boostly members, you get your own CRM. As you can see here, Ginger and Gold and what they've gone and done. If you come down to the sites, you can actually build out your own funnels and landing pages and this is exactly what, what they've done here. So if we look at property management, this is a totally separate landing page and lead generation form that they can use to get in front of homeowners. We've got Liam here you can click on there, you can book a call with them over on Calendly, which is great. You've got all the good stuff on here that you want, all the FAQs, everything, yada yada yada. But this is a separate landing page to the actual direct booking site. So it's basically management, Ginger and Gold. Now they have that link on their website, but they also have a separate domain that people can go to. So they can run ads to here, they can run social media campaigns to here, they can have business cards going to here, but it's totally separate than sending them to their, their direct booking site. Okay, because their direct booking site is for direct bookings. Now you can still have a little something here in the drunk drawer which is obviously the management page that talks about co hosting, management model, whatever you want to talk about. But it's not the first thing that people see when people first land on here which will be hipster nz, co nz, sorry. They want to be about the booking, they want to be about how to stay with you. Obviously in your drunk draw, which is the footer down here you can talk about management, but this is all about the booking experience. You do not want to be confusing because when you confuse you lose. And this is why we've updated all of our sites around this. You can see here in the heading now Homes, experiences, services. So for you again, host, co all the things that we've spoken about, getting a star using Experiences, Viator etc, totally free to get set up and it looks good but the main thing is how can they book and when they hit on the book, the book now obviously all your listings will pop up and they'll be able to go from there and they'll be able to make that direct booking with you, which is what we want. But your website needs to have a big, a big change out. If you want to come and chat to us, just go to boostly.co.uk book and again like this, this is a dummy listings that we have on here. But this pretty much now just goes and works and looks just like it would do on, on any direct booking site. And obviously then it goes from here to hospitable where they can book with your good self which looks a lot more better and cleaner on here because as you can see I'm already starting to go around the houses. But what I do really like is that you have a very clear brand, you've got a Very really nice pictures. But obviously now it's about looking after the winter months. There are still people coming to Auckland 110% but you need to stand out for it. Actually you do already brand it Industrial chic, Sky Tower Suner, Retro Rave Pad, Tropical Velvet. So again on your Airbnb listing, this is Tropical Velvet brought to you by Hipstay. This is the retrorave pad brought to you by Hipstate. This is the Sky Tower stunner brought to you by Hipstay. Every single one of your Airbnb listings, that should be the first bit of blurb at the top of your description because people will then know that you are a brand and you are a business and then they can go and find out more which is, which is great. Going down to the next bit of advice is so again not winter focused management needs to be separated but as well, what we want to really start doing is we want to build a lead generation form. We want to give people a reason to opt in and get more information about you. And something like this blog post, you can easily turn this into a PDF, you can easily turn this into a landing page. So for example, again if you come back into the Boostly CRM that again anybody who's part of Boostly, you've already got this. You can create a little funnel, a little legion where it would be opt in to find out the best, coolest, second hand vintage shops and treasure hunts for La la. Let's just use our little chat GPT to come up with it. So read this and turn it into a lead magnet generation page for my website. What would be the headline and the tagline and then turn it into a PDF so that after they sign up they get the PDF of the top secret locations to shop for all things. Okay, so I'm going to type that in Chat GPT is going to do literally all the work for me and then you can have that on your Hipstay site. It can be a little section at the bottom, it could be a pop up that comes up. But it will really help because everybody lands on your website, the conversion rate is less than a percent. It's like really small amount. But how can you change it to where Even if somebody doesn't book on your site, you can get their details, first name, last name, email address so that you can keep in touch with them. And again, you've got a lot of cool stuff on your blogs. Let's turn it into lead magnets. So the lead magnet landing page would be the ultimate guide to Auckland Secret vintage shops uncover the city's coolest, quirkiest, secondhand treasures created by locals who know where to hunt. So then you've got all the good stuff here, you've literally got all the places and you've got a little CTA at the end. So you can literally turn that into a PDF. You can put it on your website, you can hook it up to mailchimp, you can even hook it up to your boostly CRM. Because again, this is what we've got in here. We've got email automations ready to go and so you can start to get people and generate an email list. I'm not entirely sure if you've got one at the moment. Please do let me if that's the case. But if you can start to gather the emails and then with something like the booster CRM, start to use them, that'll be fantastic. So other strategic fixes, obviously, again, your current listings read neutral or summary orientated. You're definitely missing out on emotional drivers for winter, for winter guests to book. Talk about heating blankets, smart tv, tea, coffee, hot chocolate, cozy winter views, indoor comfort, which is definitely something you can definitely do. Launch some winter promos across your platforms. Again, I went to go look at the social media. Your last post was a long time ago, 27 weeks ago. But again, things like this, very cool. People love seeing videos, but again, I think we just need to take out all of the ones that don't fit. And do more stuff like this. So what is happening? What are things that's going on? So you've definitely got. You've definitely, definitely, definitely got the right sort of vibe on this. Hello, visitors to Auckland. I've got a real treat for you. Things like that is fantastic. Talking about places to visit, I would do make sure it fits, obviously get rid of that, Do more like literally a post a day. And again, if you're struggling, come on back to the. To the bot here, to our digital twin. Give me 10 different Instagram post inspiration reels for winter. And again, if you're stuck, come and ask the. Come and ask my digital twin. It'll give you all the advice that you need on posts and things and content and just post more because you've got real good. It's just you're lacking in con consistency. So here's your next ups. Here's your advice. Number one, go ahead and full Airbnb listing rewrites for the winter search. What we need for you to do is to go get new pictures of all of them. That's really focusing on winter. Then you've got a spring and summer collection and you've got an autumn and winter collection as well. What we want to be doing is we want to be. If you do have an email list, reach out to everybody that is on your list. That's probably a drive away, I'd say, you know, three, four, five hours away or maybe even Australia maybe. And focus on emailing them about what is happening in Auckland in the winter to get them intrigued, whether it's a conference, whether it's an event, whatever it may be coming up. If you haven't got an email list, we need to start building one. You've got the GPT. I'm going to paste it into here on the landing page that you need to be creating. And you can create one for loads of different types. So you can a B test this. Once you've got it, you need to update your website to make it look more like it needs to do in 2025. Nice big image, transparent menu at the top. Don't use the block bar. And when I mean the block bar, it's literally what you've got here. That's a block bar in the header and that get rid of them, have a nice transparent, nice big image. Rewrite your headline, rewrite your tagline and obviously as well, make sure it's super simple on where a guest goes from A to B to C. The next thing that we're going to say to do is start posting more content on Instagram. Please go and use the digital twin of mine to come up with content and creation ideas and then go and implement it. You can, even when you get access to obviously your Boostly CRM, you can even post on your social medias from here as well. What I'd love to see you start doing would be to brand each one of your listings so that it's clear that you're part of hipster. You are the owner of hipstate and this property. And again, you did have some really cool images here. One was called the Retro Tower. The Retro City Tower. Where is that? There we go. So Tropical velvet, I think that one's tropical velvet. Oh, that one's tropical velvet. So in the description here, it would be. This is introducing Tropical Velvet by the Hipstay brand or the hipster, whatever you want to call it, which is fantastic. Got some good action points there, Hannah. Massive. Well done. Thank you so much for putting your business forward. And to everybody who has enjoyed this. Again, the key takeaway for everybody, spring, summer, autumn, winter, different types of crowds, different types of vibes, different types of guests that are looking to book. Make sure you've got them so you can appeal. Get your email list sorted, get your lead magnet sorted, make sure your website is updated, everybody, and get posted more on socials. If you've enjoyed this, click on this one because YouTube is saying you can go watch another roast video. And if you would like me to roast your business, click on the link in the description below. And also while you're there, if you want to go and chat to my digital twin, I'll leave the link down there for that as well. I'll be back with another video next week.
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