When Is the Best Time to Book Airbnb? – Podcast 011

In this episode B and Jack discuss the best time to book Airbnb as a digital nomad. They go over the two main approaches to deal with the matter as well as the main situations when each approach is preferable.

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1. Summary

1.1. The Topic Within The Broader Digital Nomad Life System [1:37]

    • The Digital Nomad Life System is a 6-step meta-system created by us at Nomad Tactics that aims to explain how someone can go from living a non-nomadic normal life to living an optimized digital nomad life.
    • The fifth step of the system is called “Base Research and Arrangements”. Once the nomad has selected the key variables related to the base (Step 2: Base Pre-Planning), he needs to do some in-depth research and arrangements about his soon-to-be new base. Deciding when is the best time to book your Airbnb (or accommodation more generally) is one of the things you must do in this step.
    • To have a general overview of the Digital Nomad Life System you should listen to this episode.

1.2. General Considerations [5:22]

    • We are referring to Airbnb in this episode because this is the most common type of accommodation used by digital nomads. But the advice here pretty much applies to any type of accommodation you desire to rent.
    • These considerations only make sense when you considering a long stay in a place. If you intend to stay short in a place just book in advance since even if the place is not great you won’t be stuck in there for long. Therefore, it doesn’t really matter.
    • Keep in mind that when I refer to “the best time to book an Airbnb” I do not exclusively mean the cheapest time to book. I consider the price. But the price is only one factor among other things, like the availability of good listings.

1.3. The two common approaches for when to book your Airbnb [9:12]

    • When is the best time to book your long term Airbnb accommodation? Should you book all your accommodation in advance or should you wait to get to the destination to book the bulk of it there?

A. The book-in-advance approach

        • On the one hand, you can book in advance for your whole stay based on the online research you have done beforehand.
        • The main benefit of following this approach is that you will likely have more and better properties to choose from since you are booking in advance. In this case, the further in advance you book the better.
        • Moreover, another possible benefit is that you sometimes can get an early bird discount from hosts since you booking ahead of time. If you combine that with my Airbnb negotiation script you could get up to a 60% discount.
        • However, this approach also has some downsides. The main downside is that if you book your whole stay in advance and the place is bad for whatever reason (e.g. bad neighborhood, noisy, host too strict), then you will be stuck in a bad place for your whole trip. Unless, of course, there is a solid reason for a formal complaint with Airbnb (you can learn how to do that effectively by reading this article).
          • Pro tip: The best online resource to research about the good areas to rent on a destination is nomadlist.com

B. The book-it-there approach

        • The second approach is to book a place at your destination only for a short period based on your online research. You then go to the city, see the Airbnb and decide if you will stay there for the entirety of the trip or if you want to change the place.
        • The main benefit of this approach is that you can arrive at the city and assess the place prior to totally committing to it. If the place, or anything related to the place (e.g. location), is bad, then you can easily change it with no great financial loss.
        • The main downside of this method is that, even if you like the initial place, sometimes it won’t be available anymore for the entirety of the trip. Somebody else might have booked the remaining days. Therefore, you might need to look for an alternative place to stay on and since it will be a last-minute booking, you might have very few good Airbnb options.

1.4. When is the Best Time to Book Airbnb? Which Approach to Use?

    • In order to determine when is the best time to book Airbnb, we need to take two factors into consideration.
      • The popularity of the city: How popular is the city of the Airbnb you intend to stay in? The popularity of the city will depend on how touristic the city is in general and, in which season you are planning to go there (i.e. low season or high season). The greater the popularity, the higher the demand for Airbnbs. So let us assume, for the sake of this article, that we can classify cities as popular or unpopular.
      • Canceling policy: How flexible is the cancellation policy of the Airbnb you intend to stay in? Airbnb hosts can set different types of canceling policies. These policies affect you when canceling before and after check-in. The more flexible the policy, the less financial loss you will have if you decide to cancel your stay. So let us assume, for the sake of this article, that we can classify canceling policies as more-flexible or more-strict.
        • Pro tip: If you click here you can find the specific details to do with all types of cancellation policies.
    • Once we have considered these two factors, the answer to the question regarding which approach is better becomes more evident. It will depend on the combination of these two factors just outlined.
      • The book-in-advance approach is better
        • When this approach preferable?
          • If you are dealing with a popular city combined with a more-flexible Airbnb refund policy
        • Why is that?
          • No risk of not being able to stay in the initial place; due to already having the place booked for the entirety of the trip.
          • No risk of a great financial loss if you do not like the initial place and want to change it; due to flexibility of cancellation policy.
      • The book-it-there approach
        • When this approach preferable?
          • If you are dealing with a unpopular city combined with a more-strict Airbnb refund policy
        • Why is that?
          • No risk of not being able to find another place; due to the low demand for Airbnbs in the city.
          • No risk of a great financial loss if you do not like the initial place and want to change it; due to not booking for the entirety of the trip in advance.
      • But what if the other two alternative scenarios are the case? Namely, [unpopular city/more-flexible policy] OR [popular city/more-strict policy].
        • If any of these two alternative scenarios is the case, then the choice will not be so clear cut. Both approaches are reasonable.
        • The approach you adopt should depend mostly on how risk-averse you are. In other words, how willing are you to commit to a property you only researched online and how willing are you to accept that you might not have great alternative options if the initial Airbnb is bad.

2. Transcript

B: Hey hello welcome to the nomad tactics podcast here provide life optimizing tips and systems for digital nomads I will host B. and I'm joined once again by the co host Jack.
B: The topic we're going to talk about today is when to book your Airbnb or more generally your accommodation I would start with a quick summary of the episode. first me and Mr. Jack gonna talk about how this topic relates to our broader digital nomad life system after that we gonna make some general considerations regarding the topic then we gonna talk about the two most common approaches used by digital nomads for when to book accommodation and finally we gonna talk about in which situations each of those approaches are appropriate I hope you enjoy the episode.
Jack: Hey hello Mister B..
B: Hello Jack.
Jack: So the topic of the day is when's the best time to book Airbnb or more generally the accommodation.
B: Yeah that's right.
Jack: And the thing as usual it is almost like our custom now we should talk about the topic and how it relates to our digital nomad life system.
Jack: And for people who don't know what is our system it is a six step system aims to help people go from a non nomadic lifestyle to live an optimized digit normal life and the thing the topic today lies in the third stop of the system which is called base research and arrangements.
B: That's correct so yes as you said the topic fits the third stop and I gonna provide very quick overview of the third step of our system so once the nomad has selected the key variables related to his new base that's he should have done in step number two on what we called base pre planning and the key variables here is where is he going with who when is he going things like that then he needs to go to the next step of the system the base research and arrangements and in this step the digital nomad needs to do some in depth research regarding his new destination and one of the things he should research and think about is when is the best time for him to book his Airbnb if you're not familiar with our digital nomad life system I strongly encourage you to go to the second episode of this podcast and have a listen because there we provide a general overview.
Jack: We explained in great details of what the system is in the second episode yet so I think before we go into the main topic of today you should consider some important points like the first one is why we choose Airbnb as an example.
B: Yeah.
Jack: It is because we think did you know men use Airbnb the most when booking accommodation but the advice you're pretty much apply to any type of condition you want.
B: Yes yeah so Airbnb is the one you're going to be using and of course throughout the episode we gonna talk about certain things that are specific to Airbnb but as you just said overall the advice would apply to other types of accommodation as well such as all other websites that are somewhat similar to Airbnb or even when you're booking a hotel or hostel so another point I would like to make has to do with the fact that the advice today is most relevant when you're considering long stays.
B: If you are going to a place and you intend to stay very short let's say you just a couple of days or weekend.
B: I would simply say don't worry about when is the best time to book just research the best you can and book in advance and the reason for that is because since you staying just a couple of days in the worst case scenario let's say the place is not really great it won't be such a big deal you're simply going to you know stay in the place that is not amazing but it's just for a few days so it's not such a big harm. Another point that I would like to talk about it has to do with the fact that when we mention the best time to book an Airbnb we are not exclusively talking about the cheapest time to book so the price is one of the things we are considering here but we go beyond that so there are other factors that we are also considering and among these factors I think the main one is the number of available options you have.
Jack: I see so let's go into the main topic of today when is the best time to book the Airbnb so here we have two common approaches and the first one is what we call the book in advance approach.
B: Yes that's right so the book in advance approach can be very simply summarized when a digital nomad going to research in advance and he going to book the entirety of his stay in advance of course this approach has a couple of positive sides so the first one has to do with the fact that if you're booking in advance is very likely that he will encounter a lot of options for you to book and by following this rationale the further in advance you book the more options and the better options you're going to have available to you thinking exclusively in terms of Airbnb there's another possible benefit that is you might get that early bird discount are you familiar with those types of discounts Mr. Jack
Jack: You mean those one you can if you book in.
B: A couple of months before.
Jack: Yeah yet month before and you can get like a certain amount usually around thirty percent yeah.
B: Yeah so it's up to the host how how much discount they want to give but yeah it's basically some hosts offered this option where if you book let's say two or three months before the actual check in and you're going to get an extra discount and is going to be on pop off let's say your long term stay discount that you probably get ready gonna have yeah so that's great another good benefit.
B: But of course this approach has some downsides the main downside is the fact that if you book the entirety of your stay in advance and for whatever reason you don't like the place maybe the neighborhood is not that good maybe it's a very noisy place let's say there is a construction site next to it or maybe the host is too strict doesn't really matter why if the place is bad most likely you're going to need to stick with it no matter what.
Jack: So this second approach we got here is what we call the book-it-there approach.
B: Yeah so the book-it-there approach is basically when the digital nomad gonna book an Airbnb just for a few days in the new city he's going to and once he gets there he going to check it out the place he feel like it and then decide if you're going to book the entirety of the trip to stay there or is he going to book another place in other words if you gonna change place as you guys can probably imagine that this approach has also some benefits the main benefit being that you're gonna be able to arrive in the city assess the place prior to totally committing to it.
B: If the place or anything related to the place such as the location or the host whatever is bad you gonna be able to change without the great financial loss because as I said in the initial description you just booked for a few days also there are some downsides to this approach and the main downside being that if you only booked for a few days but you like to place very much and you'd like to stay being part of the trip there there is a possibility that someone else might have already booked for the remaining days therefore even if you do not desire to do so you're going to be forced to change place and that change going to be done on the last minute since you're ready on the city and you probably won't have that many good Airbnb options available to you.
Jack: I see so Mister B. since we talk about the two most common approach here which one you do you think is the best or other anything factors to consider when choosing this the best approach.
B: Yes Jack so I wish there was a simple answer.
B: And I could simply tell you this approach is better than the other one but I think the answer is very much contextual so in order to determine when is the best time to book the Airbnb i.e. which approach you should use we need to take two factors into consideration the first one is the popularity of the city in other words how popular is the city of the Airbnb you intend to stay.
B: The popularity of the city of course can be determined by how touristic the city is in general and also in which season you're planning to go there is it low season or high season and the reason why it's important to determine the popularity of the cities because the greater the popularity of the city the higher the demand for Airbnb so that's the the crucial point here the second important factor for you to consider is the cancelling or the refund policy of the Airbnb you are considering to rent in other words we could think in terms of how flexible is the canceling policy of the Airbnb Airbnb host can set different type of cancelling policies and we gonna link in the show notes the U. R. L. that show the different types of canceling policies and if I'm not mistaken there are five different types that go from very strict to very flexible a very strict would be if you decide to cancel your stay you don't get any money back a very flexible would be if you decide to cancel your stay you get basically all your money back this policies we will affect you when canceling before and after check in and the more flexible the policy is the last financial loss you will have if you decide to cancel your stat so the canceling policy is the second important factor to be considered here.
Jack: I see so once we take the two factors the popularity of the city and the canceling policy into account which approach which will be better is more obvious now yeah it really depends on how.
B: We combine these two factors.
Jack: Exactly so Mister B. when this the book in advance approach better.
B: So it seems to me that the book in advance approach is better when we are dealing with a city that is both popular and also the Airbnb that you're considering to rent has a more flexible refund policy the reason for that I think it's quite obvious on the one hand since you used to book in advance approach you won't be facing the risk of not being able to stay in the initial place you booked for the entirety of your stay this is because of course you already booked the entirety of the stay right and that's a very popular city and would be a big risk if you like the place but you could not stay there because you would be forced to move out and you would not have a lot of Airbnb options to choose from.
B: On the other hand the other good benefit of booking in this scenario is that you won't face the risk of a great financial loss if you do not like the initial place and that's because the Airbnb offers a more flexible refund policy and in the case you don't like the Airbnb you can simply go to another one and you won't have a great financial loss.
Jack: I see but Mr B. win this the book-it-their approach better.
B: Soul the book at their approach seems to me is more beneficial in the situation that is the polar opposite of the one I just described so that's when you're dealing with a city that is unpopular combined with a situation where you are considering to stay the Airbnb the offers a more strict refund policy and the reasons for that again are quite straightforward the first reason is that you are not facing the risk of not being able to find another place because the city is not that popular so even though somebody else might have already rented Airbnb and we too are staying on for the remaining days you won't have a problem because the city is not popular surely you will have a lot of Airbnb options.
Jack: Also.
B: You won't be facing a great risk of big financial loss since you did book for the entirety of your stay you won't lose a lot of money.
Jack: I see so here we talk about to two scenario yes and.
B: Which is a popular city with more flexible Airbnb refund policy and them popular city with some more strict Airbnb refund policy.
Jack: Yes so how about the two weeks in there that a a puts it to the one you just mentioned.
B: So you mean an unpopular city with a more flexible Airbnb refund policy and the popular city with more strict refund policy.
Jack: Yeah that's a big mouthful but that's what I'm saying.
B: Yeah I guess in those two cases which are very possible cases there won't be very much.
B: A clear cut optimal solution so both approaches.
B: The book-it-there approach and the book in advance approach are reasonable and the way I think you as a digital nomad should choose which approach to take will depend very much on how risk averse are you in other words how willing are you to commit to a property that you only researched online therefore you're not that certain about and also how willing are you to accept that you might not have a lot of options in terms of Airbnb if the initial Airbnb is bad so.
B: In this case in this two scenarios.
B: I think it's more of a subjective choice I'm quite curious Mister Jack which alternative would you prefer in these two scenarios.
Jack: Personally I still like the played by that year's approach basically this is the book at their approach because I like to actually go check out the city and know which area I like the most for like neighborhood I might find a housing there.
B: I see so like you are okay go there and check it out but maybe you don't have that many options.
Jack: Yeah I may be the worst case scenario find hostel and it tasted function.
B: And I think that's perhaps because you have a couple of bad experiences when you rented in advance and you will go out there and you didn't like the place I remember you told me a couple of cases yeah I'm I I would say I'm the opposite I.
B: I preferred to book in advance approach more if I'm dealing with one of these two scenarios in popular city with a more flexible policy were popular city with a more strict policy and that's because I don't know I just
B: Prefer to do as many arrangements beforehand and just get there and focus on other stuff.
Jack: I see that sounds great so Mr. B I think this is the end of the episode do you want to add anything to this.
B: perhaps just reiterate that we used Airbnb as an example but a lot of the principles behind two approaches can be applied to other types of accommodation we use Airbnb because is as you said in the beginning Mister Jack the most popular among digital nomads and also I just would like to ask people to leave a review we are in a new podcast and we would very much appreciate if you guys could leave a review that would.
Jack: Help out a lot yeah thank you for listening.
B: Thank you very much

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3. Resources

  • Find information about different neighbourhoods in a city: Nomad List
  • Airbnb cancelation/refund policies: Airbnb Policy