When buying something, how often do you consider buying that something used? Whether that something is a car, house, appliance, bicycle, article of clothing, piece of furniture, etc., how often do you give real consideration to buying one that has already been used by someone else - instead of one that is shiny and new?

When it comes to normal, everyday life, we want everything to be new. However, when it comes to traveling, absent some rare exceptions, everything is used. Think of the airplane seats you sit in, the rental cars you drive, the hotel rooms you stay in, the tours you book, the well-worn paths you walk, and even the sights you see. All are used. Hundreds and thousands of other people have preceded you. And we accept this without qualm or complaint.

But, there’s a difference, isn’t there? Those used airline seats and hotel rooms are professionally maintained in such a way that they become indiscernible from each other. There’s a certain standard to which they conform. As a result, you don’t have to suffer through messy inconsistencies. The same can’t be said when buying used in normal, everyday life. Buying a used bicycle, article of clothing, or piece of furniture means researching, inspecting, analyzing, scrutinizing - inconvenient activities that take time and effort.

There’s now a relatively new option in the world of travel that can cause the traveler to suffer through the same messy inconsistencies that is typical of normal, everyday used. That option is Airbnb, the online marketplace for people to rent short-term lodging. If buying used (in your normal, everyday life) just isn’t your thing, then staying at an Airbnb when traveling probably wouldn’t be, either. Buying used is typically inconvenient, time-consuming, and risky (at least relative to buying new). The same can easily be said of booking and staying at an Airbnb. Why bother with either?

When buying used, you can realize a number of advantages:

  • save money
  • make efficient use of resources
  • score unique, well-cared-for, and/or high-quality finds
  • break out of the standard cookie-cutter consumer/retailer bubble
  • direct your dollars toward individuals and small businesses rather than faceless corporations

Unsurprisingly, the same advantages can be realized when staying at Airbnbs (as opposed to chain hotels). But, equally unsurprisingly, selecting, booking, and staying at an Airbnb can be an intimidating, daunting hassle. If you can see the advantages in going the Airbnb route, and find them appealing, but have found yourself too overwhelmed by the fear of unknowns and gotcha’s to take the plunge, you might find the below advice very helpful.

Assumed Amenities

Truth be told, there’s something (good things) to be said about those standardized cookie-cutter chain hotels. At a certain, fundamental level, you know what to expect out of them. They are going to be in a fairly safe, central location, with a front desk at which you check in. You’ll be given a room, with a door, that has a lock, and some sort of key. The room will come with a private bathroom and shower, and will have been professionally cleaned before your arrival. If you don’t get one or more of these basic things, you can feel safe in knowing that you have every right to complain.

On the other hand, when you’re on the Airbnb site looking through a listing, it’s best to just assume that everything is off the table. As such, it’s up to you and your due diligence to make sure that anything and everything that is important to you is explicitly put back on the table. The Airbnb site takes a stab at surfacing amenities that might be lacking in any individual Airbnb by listing them out for hosts to mark as being included. They account for amenities that you would just assume be included in a standard hotel (e.g., heating, air conditioning, TV, smoke detector, hangers, locking bedroom door, shampoo, fire extinguisher, etc.), but then go beyond them to account for amenities that are more characteristic of homes, not hotels (e.g., kitchen access, washer, dryer, wifi, indoor fireplace, game console, etc.).

On the Airbnb site, though, all of these amenities get lumped together, treated with equivalent importance. As a result, mentally, it can become tiring always having to make sure that every listing you consider includes all of your “assumed” amenities, while also taking the time to explore and appreciate the “bonus” amenities that can make an Airbnb special - or a bargain. The Airbnb site addresses this somewhat by allowing you, the guest, to filter Airbnbs by a subset of these amenities. If you consider the lack of air conditioning to be a deal-breaker, then you can filter out those Airbnbs that don’t offer air conditioning.

With that being said, aside from wifi, I’ve never considered the lack of any amenity to be an absolute deal-breaker. After all, every Airbnb is unique. As such, who am I to say that a host’s home or room should be excluded from my consideration because it has no air conditioning (for example)? Maybe it’s below ground, or has an excellent cross-breeze, or is sheltered by large shade trees. Who knows? I certainly don’t presume to.

As a result, I end up opening the flood gates and then do my best to sort through the listings on a case-by-case basis. Which, as I sad before, requires me to assume that, with each listing I review, everything is off the table.

Missing Amenities

I don’t blame you if you consider this to be an unnecessarily inefficient approach. But, I stick with it because the Airbnb site will never be able to completely and comprehensively account for every “assumed” amenity. “Like what?”, you ask? Well, how about a door on the bathroom? Or how about screens on the windows, a smoke-free bedroom, a shower with enough room to bend down, a cold refrigerator, accessible electrical outlets, and bedsheets without holes? You would think all of these “amenities” would be “givens”, and yet we’ve come across all of these “misses” and more in our 3+ dozen Airbnb stays.

Many of these “misses” can be chalked-up to the unique and individual nature of Airbnbs, with each owned and operated by a host with their own set of widely-varying standards. If not that, then sometimes I’ve seen such “misses” brushed aside with the thought/comment that you’re staying at someplace inexpensive and bare-bones, so what else would you expect? Whether or not you agree that either of these arguments adequately justify such “misses”, you should realize that they exist.

There are also many “assumed” amenities which simply cannot be considered “givens", especially once you leave the U.S. These include things such as drinkable water from the tap, a toilet in which you can throw toilet paper, a wall mount to hold the shower head, and a curtain or door on the shower. Such “misses” reflect the cultural and regional differences in how people across the world live their lives. The relative homogeny offered by multi-national hotel chains should not be expected out of Airbnbs. And I wouldn’t expect the Airbnb site to systematically account for these regionally-specific “deficiencies”, at least not anytime soon.

The first Airbnb we stayed at was in Aruba. It was located well away from the resort/hotel zone. The Airbnb had a toilet in which you couldn’t throw toilet paper - the first time we had ever encountered such a restriction. (Instead, you discard your used toilet paper in a small waste basket placed next to the toilet.) This was definitely outside of our comfort zone, but we adapted to it quickly enough. And it’s a practice we have since encountered during subsequent stays in other countries.

Upon our return home (to the U.S.) from Aruba, we’d find ourselves recalling our trip to Aruba “veterans”. In every single instance, when mentioning the no-paper-flushing practice to these folks, we got blank stares. None of them had ever heard of such a restriction. Such is characteristic of the difference between staying in the resort/hotel “bubble” and staying “local”. When staying at Airbnbs, don’t expect to be insulated from what you may consider to be peculiar features and practices.

So, if the Airbnb site isn’t going to help you catch the absence of any of your “assumed” amenities, what are you expected to do? You do your own legwork - or not. Ultimately, it’s up to you how much you want to sweat the details, and which details you want to sweat. Out of the nearly dozen “misses” I’ve listed above, which we have experienced first-hand, I only keep my eyes peeled for 2 or 3 of them when reviewing listings these days. While annoying at the time, the others didn’t prove to be impactful or ruinous enough to warrant an ongoing, front-of-mind position in my head.

I was recently looking through Airbnb listings for a place for us to stay - somewhere in France. I came upon a gorgeous, well-priced private room that looked like a winner. However, upon studying the photos and/or reviews, I realized that there was no door on the bathroom connected to the bedroom. Even worse, the toilet was in clear and hard-to-miss sight of the bed. Neither of us enjoy watching each other use the toilet, so I removed that Airbnb from consideration.

Bonus Amenities

On the other hand, the inclusion of “bonus” amenities can really “make” a stay. Such “bonus” amenities tend to be very location-specific, or subject to individual tastes, so it’s only appropriate for certain individuals to factor them in when evaluating certain listings. For example, when looking through Airbnbs to stay at for beach vacations, I always keep my eyes peeled for mentions of beach chairs and umbrellas included with the Airbnb. I love me a chair and shade when on the beach. As such, scoring an Airbnb that includes them can be worth $5 to $10 for me. It’s a (non-standard) amenity that I would end up having to pay separately for, anyway.

We once stayed at an Airbnb in Barbados that included beach chairs. The chairs turned out to be very high quality beach chairs - better than any we’ve ever used. We were so pleased with them, when we returned home, we decided to buy our own pair of those same chairs.

In congested areas in which you’ll have a car, the inclusion of a free parking space with an Airbnb can save you both money and stress. In regions/countries where the tap water is not safe to drink, the inclusion of filtered water bottles (and dispensers) with an Airbnb can, again, save you both money and stress. Some Airbnbs include free use of bicycles, thereby allowing you to save on transportation costs (and have some fun getting around, too). I’ve even seen Airbnbs provide free use of included member/resident passes to local attractions, saving you more money.

We once stayed at an Airbnb in Turks and Caicos that included the use of two bicycles. The Airbnb was located such that these bicycles allowed us to get by without needing to rent a car (aside from one day to explore further-flung parts of the island).

When we visited Monterey, California, we stayed at an Airbnb that provided complementary use of two guest passes to the Monterey Aquarium. This saved us upwards of $100!

If doing all of this scrutinizing sounds like a lot of work, that’s because it is. But, the steps involved in performing that scrutinization are steps that you should be performing with every Airbnb listing, regardless. Scrutinize the listing description and photos provided by the host and read through the reviews written by past guests. It’s in these elements of the listing that you’ll find mention of any "non-systemic" caveats or “deficiencies” - and also features and “bonuses". And if you are left guessing on something, send a message to the host and ask them about it.

Listing Description

For me, the listing description provided by the host is the most important element of the listing. A brief or superficial description is a huge red flag. In my mind, this either means that they’re lazy, they don’t care, they’re hiding something, they don't communicate well, or they’re too busy. Regardless, none of these reasons are acceptable, in my opinion. A host does not need any special talent or equipment to put together a solid, detailed, helpful description of their space. As far as I’m concerned, the more expansive the description, the better. Even if I, the potential guest, doesn’t care all that much about the details of the host’s space, I want the host to care - passionately.

If the host isn’t a strong-enough writer to put together a solid listing description, how clear are they going to be in their communications with you as a guest? With Airbnbs, most communication is via Airbnb messaging - or texts. And a lot of Airbnbs have self check-in procedures, such that you’ll never meet the host. Instead, the host will send you any necessary lockbox, door, and/or gate codes within 24 hours prior to your arrival. And every set of check-in instructions is different. You want those instructions to be well-thought-out and clearly communicated. In comparison, writing a description for their listing is rather easy.

If the host is too busy to put together a solid listing description, how responsive will they be to any issues you encounter while staying at their place? It may be that they have a demanding job that will prevent them from properly attending to you. It could be that they manage a number of Airbnbs - too many to attend to satisfactorily. It could be that they have time-consuming family commitments. Regardless of the reason, a host that can’t find the time to write a good description for their listing - once - may not do a very good job of attending to their guests on a day-in/day-out or week-in/week-out basis.

Listing Photos

The second-most important element of the listing are the photos. As the potential guest, try not to get too hung-up on the quality of the photos. Instead, try to focus on the substance of the photos. After all, a host’s photography skills shouldn’t act as a reflection of their hosting abilities. As long as the photos aren’t sloppy, blurry, confusing, improperly-oriented, etc., a host can be forgiven for not providing professional-quality photographs. However, the content of those photographs are definitely eligible for judgement.

When reviewing a listing, I want to see, at a minimum, multiple photos of the bedroom and bathroom, from various angles. If there’s a kitchen in-play, I want to see the same for that room, as well. With regard to the bathroom, I want to see the sink, toilet, and shower (and door 😛). Ideally, I should be provided enough photos of the space from enough angles that I’ll be able to mentally construct the layout and floor plan of the space.

We once stayed at an Airbnb in Vermont - a private bedroom and bathroom. However, the listing did not include any photos of the bathroom. Despite this miss, I decided to book the Airbnb. Fortunately, upon arrival, the bathroom turned out fine and we had a wonderful stay with a wonderful host. During our stay, in one of my conversations with the host, I mentioned her omission of the bathroom in the listing photos. She said that she had never really thought of including it, but agreed that she should. She has since updated her listing to include a photo of the bathroom. :)

Beware of photos of a messy or cluttered space. Odds are high that reality will be worse. Be equally aware of a spartan or empty space. It could be that the host has put a bare-minimum of effort into furnishing it. On the other hand, award the host some bonus points for including photos of the exterior of the house/building, especially if it gives you a sense of the parking situation. If the host is thoughtful and thorough enough to provide a screenshot of the Airbnb located on a map, that tends to be a great sign.

We once stayed at an Airbnb in Punta Cana, Dominican Republic. The Airbnb’s listing included a Google Maps/Earth screenshot of the Airbnb’s location relative to the beach, which was great. Unfortunately, that Airbnb turned out to be the worst one we ever stayed at. In the end, the inclusion of the screenshot turned out to be a false sign of quality.

Frequently, hosts will include photos of area sights and tourist attractions. These are OK, but not if they come at the expense of an adequate number of interior photos of the space. You and I know that Walt Disney World is in Orlando and that the Golden Gate bridge is in San Francisco. We don’t need the host to remind us of that. However, if the Airbnb offers up a view of- or short walk to- a specific attraction, such as a nearby beach, the inclusion of an appropriate photo makes sense.

As I stated before, try not to get hung-up on the quality of the photos. It’s OK if they are a bit dark or unsaturated. On the flip side, try not to become too enamored should a listing have gorgeous photos. You wouldn’t think gorgeous photos could be problematic; however, I’ll assert from experience that they can be. Firstly, gorgeous photos can distract you from paying proper attention to the fundamentals, such as picking up on missing amenities. If you can maintain your focus, then this won’t be an issue for you. Secondly, gorgeous photos can leave you disappointed with reality when you first see the space with your own eyes. Perfectly staged, brightly-lit, softly-focused photos can be used very effectively to “hide” the warts of an otherwise pedestrian space.

We once stayed at an Airbnb in Tulum, Mexico. The photos included in the listing for it were very, very well done. I was really looking forward to staying there. However, it turned out to be the only Airbnb we’ve ever stayed at where we had to deal with big, fat cockroaches. The cause was no mystery - big air gaps at the bottom of the exterior doors that vermin could easily crawl through. The Airbnb had a number of other, easily-addressed issues. I was left wishing that the host had spent some of the time they had used taking photos on, instead, fixing the nuisance issues in the Airbnb, itself.

With all those caveats being stated, a comprehensive set of high quality photos cataloging an attractive space is hard to fault. Likewise, a small set of low-quality photos of an unattractive space is hard to give the benefit of much doubt. While a host can be forgiven for pedestrian photos, it’s hard to trust a host who isn’t embarrassed by flat-out bad photos.

Guest Reviews

The third-most important element of the listing are the guest reviews. While the host has complete control over the listing’s description and photos, they have no control (well, very little control) over the reviews that guests submit for that listing.

If you think that you can ignore the individual guest reviews in favor of simply focusing on either the overall or constituent star ratings, I encourage you to rethink that approach. I say this because I’ve found that Airbnb guests tend to be quite generous and a bit overly-positive when reviewing. I don’t believe I’ve ever seen a listing with anything lower than 3 stars, which is remarkable given that I tend to shop amongst the lowest-priced Airbnbs.

When Airbnb guests do decide to express any negative sentiment, it is less likely to be reflected in the rigid, unforgiving star ratings and, instead, more likely to be delicately and diplomatically factored into the free-form reviews. And, even there, negatives are frequently either glossed-over or simply not spoken to. As such, you need to read through a good number of reviews for each listing to understand the true positives and negatives of the Airbnb. In general, the longer the review, the more valuable and helpful it tends to be. With the shorter reviews, you have to read between the lines.

For example, take this randomly-chosen review: “[Host] is an incredibly thoughtful host. Thanks so much for everything.” While it’s nice to know that the host is thoughtful, this short little review isn’t very helpful, not when it sits nestled among other, longer reviews that raise concerns about the neighborhood being dangerous, the walls shared by adjacent apartments being thin, and the bed sheets not being changed between guests. And these are reviews for a 4 1/2 star Airbnb!

Looking at such a combination (of a high star rating and “mixed” reviews), you might be a bit perplexed. Doesn’t seem to add up, does it? But, even the reviews that mention those concerns I've listed above skew positive, finishing up with phrases such as “excellent stay”, “positive, enjoyable stay”, and “I would highly recommend this place”. Such is the nature of Airbnb guests, it would seem.

This may stem from the largely non-professional nature of many/most Airbnb hosts. By and large, Airbnb hosts are normal people like you and me. They just happen to have taken the plunge and allow strangers to stay in their “home”. As a guest, you message back and forth with them, meet with them, maybe have long conversations with them, maybe even dine with them. Many hosts are opening up their private, safe spaces to you. There’s an implicit trust being made in you. When looking at it from that perspective (and reflecting back on the feelings we’ve wrestled with personally when rating and reviewing our own stays), it can feel mean and cruel to criticize a host and/or their Airbnb.

We once stayed at an Airbnb outside of Charleston - a private bedroom and adjoining bathroom. The host seemed very nice, but we never met her, despite the fact that she lived there. In my review, we gave her 5 stars across the board. However, within my overall glowing review, I mentioned that the wifi had proven to be hit-or-miss.

The host responded to my review, apparently quite upset. She openly despaired over me giving her her first “negative” review, stating that she wished I had said something during our stay, thereby giving her a chance to address the issue. While I thought the wifi issue was worth mentioning for the benefit of future guests, I didn’t see it being worth the stress I had caused a nice person. As a result, I edited my review to remove mention of the wifi issue. It’s because of coercion such as this why I stated earlier that hosts have a small amount of control over guest reviews, rather than none.

Price could also be a contributing factor to the generosity of guest reviews. After all, the listing I pulled the above examples from is for a 1 bedroom apartment with a private bathroom in central Paris for $56/night. When you are paying so little for accommodations in a location that would, otherwise, blow the budget, you tend to be forgiving. In fact, I’ve seen this sentiment explicitly stated by hosts in response to negative reviews - along the lines of “It’s a cheap place to sleep at night. What did you expect for that price?”

Given the forgiving perspectives that guests tend to bring when writing their reviews, how you approach those reviews depends on your own perspective. If you tend to be similarly forgiving, you might be fine taking the reviews at face value. Or, if you recognize that you tend to be more demanding, or more easily-bothered by problematic details, I suggest that you focus on the specifics surfaced by the guests’ reviews, rather than the general sentiment. Gather up the specifics, construct a mental model of the space, and then make your own decision.

Some of the most important mentions that you should keep an eye out for when reading guests’ reviews are of those characteristics that cannot be captured in photos, namely issues with noise, odors, and “feel”. Make special note of comments that call out noisy neighbors, recommend ear plugs, and warn-off light sleepers. Or those that mention mustiness or smelly rooms. Or those that speak of the neighborhood feeling dodgy, tell of guests finding themselves "uncomfortable", and discourage solo female travelers. Regardless of the number and quality of photos included in a listing, photos can’t capture everything. And it’s very rare to find a host to be forthcoming about such ambient matters in the listing description.

This is why I tend to avoid Airbnbs with either no or few reviews. As long as other, well-reviewed, well-priced Airbnbs are available within the vicinity of my target location, I don’t see the point in taking a risk on an unreviewed or lightly-reviewed Airbnb. With that being said, it can sometimes be worth making an exception. A wise host will understand that a lack of reviews breeds reticence among guests, and will lower the price on their listing appropriately. If you find an unreviewed space that has been under-priced for this reason, and if the listing has solid amenities, a great listing description, and a great set of photos, the space might be worth considering.

We once stayed at an Airbnb in Ithaca, New York. When I first saw the listing, it had either no reviews or only 1 review. Despite this, the other well-executed portions of the listing, combined with a low price, gave me enough reason to put it at the top of my list of Airbnb possibilities. However, life got in the way and it took me a few weeks before I put in the booking request. By that time, the host had accrued a number of glowing reviews and, subsequently, raised his price. In the end, it turned out to be a solid Airbnb.

In such a situation, you could also click-through to the host’s profile. If the host happens to own/manage one or more other well-established, well-reviewed Airbnbs, I wouldn’t hesitate to book that host’s newly-listed, unreviewed Airbnb. What you’ve got in that situation is an under-priced gem managed by a good, experienced host. I say this with my assumption being that, unless there are extenuating circumstances, a host will manage multiple Airbnbs to similar standards.

We have an Airbnb booked for a stay outside of Lyon, France. When I booked it, it had no reviews. It was also priced rather low. However, the host had another similar Airbnb listed with 47 reviews and 5 stars across the board. Based on the host’s excellent track record with their other Airbnb, I’m guessing that the Airbnb I’ve booked will turn out to be a great deal.

Hosting Motives

A host having multiple Airbnbs under their purview can be either a positive or a negative. Through managing multiple Airbnbs, a host might have gained hard-won experience that the host then uses to both find opportunities to delight- and head-off potential issues for- future guests. Or, through managing multiple Airbnbs, a host might have accumulated exhausting experience that results in jaded indifference to guests’ issues and a lack of energy to maintain levels of quality. Either scenario is possible.

Actually, these scenarios remain valid regardless of the number of Airbnbs a host manages. The affects of experience can be the same even if only one Airbnb is being tended to. Regardless, I imagine that which scenario is in play is driven largely by the host’s motivations. Is the host driven by a passion for hospitality first, and profits second? Or are they driven by profits first - and second? Passion, not profits, is what drives a host to go above and beyond for their guests on an ongoing basis. The only way in which profits can do the same is by first manifesting as passion.

With all of this being said, don’t simply put on blinders to those hosts who aren’t in it for pure and altruistic reasons. In isolation, try not to make judgments about either an Airbnb or its host based solely on what you suspect to be the host’s motivations. What’s more important is to simply be aware of those motivations when reviewing a listing, as it can help you better understand the character and nature of both - the host and their Airbnb.

We’ve stayed at amenity-rich, individualized, owner-occupied Airbnbs in the past - frequently to great satisfaction. We’ve also stayed at spartan, impersonal, owner-off-premise Airbnbs - and they’ve been fine, too. Either can make for a good stay. What I find important to know is which Airbnb is which at the time I’m booking it. If I book an Airbnb knowing that it is little more than a source of income for the host, I know what to expect and adjust accordingly. I expect functional, get functional, and have no reason for hard feelings.

Conversely, suppose I book what I expect to be someone’s TLC-filled pride and joy. If, instead, I find it to be very much not, I feel misled and disappointed. I expect something more than functional, get functional, and have ample reason to be a little bitter. If you suspect that you’d react in the same way, do your best to sniff out the nature of the host and their space.

The “host” for a given Airbnb could, in fact, be a faceless rental agency - or a small hotel. The trouble I have with these hosts is that they consider their rentals to be largely interchangeable. As a result, they get sloppy with their listings, intermingling photos for different units in each individual listing. As a result, it’s difficult to get a handle on what exactly you’ll get. In fact, the unit you get may be randomly chosen for you when you arrive. Or, given enough vacancies, you might be given the opportunity to freely choose amongst what is available.

We once stayed at an Airbnb outside of Galway, Ireland that turned out to be some sort of cross between a private home, a hostel, and a dormitory. It wasn’t bad, but wasn’t what we were expecting. As such, we were a little thrown off and disappointed. On a different occasion, we once stayed at an Airbnb on the island of Santorini, Greece that was, in actuality, a small, family-run hotel. With that one, this was what I had been led to expect. As such, we were fine with what we got.

Just realize that there’s a wide spectrum of different types of Airbnbs. I’ve only covered two disparate points on that spectrum. There are many points in between, so please remain open to encountering many shades of grey when it comes to evaluating Airbnbs. Not every surprise is bad.

We once stayed at Airbnbs in Cancun, Mexico and Playa del Carmen, Mexico. Both Airbnbs were managed by the same host. In fact, the host had more than 10 listings on Airbnb. In general, I find such situations disconcerting, doubting the host’s attention to detail and willingness to provide anything above the level of functional. However, his listings were very well done and the host did a good job of presenting himself in a genuine way.

The impression that I got was that the host had gradually come to develop a solid design for his nicely-renovated Airbnbs and was iterating on a successful template that resulted in lots of happy guests. His motivations appeared to be a healthy mix of passion and profits. This is what came through in his listings and this is what we found to be the case in-person during our stays (which we very much enjoyed).

Playing with Dates

You’ll find the unique nature of each Airbnb also reflected in each host’s booking calendar. Generally speaking, you should approach booking an Airbnb differently than you would other aspects of a trip - airline tickets, hotel rooms, and rental cars. When making such reservations, there isn’t much chance of booking too early. For instance, many airlines will accept bookings for flights a full year out from the departure date. Unfortunately, with Airbnbs, acting that far in advance of your arrival doesn’t work very well.

If you try to book an Airbnb that shows availability for your dates, but many, many months prior to those dates, you might very well be declined by the host. This could be because the host hasn’t yet updated their booking calendar to account for conflicts with your dates. Or it could be because the host has plans to move out of or sell the space prior to your dates. Or the host may currently have long-term renters in the space and they don’t yet know whether they’ll renew the lease. Or they might simply want to maintain some flexibility in their calendar while the dates are so far out. I’ve encountered all of these, first-hand.

Even if your far-off booking is accepted, don’t be shocked if your booking is canceled as your dates near. Airbnb hosts are normal people, frequently listing rooms in their personal homes - or those homes in their entirety. As with all normal people, the unexpected can happen, which may force your host to cancel your previously-accepted booking. The further in advance you book an Airbnb, the greater the likelihood this could happen. As such, try to remain flexible.

We’ve had Airbnb hosts cancel on us as far as 6 months in advance and as close as 2 weeks in advance. In the 2 weeks instance, Airbnb stepped-in and credited $50 to my account (on top of refunding my booking). They did this without my asking, but it was very appreciated. I’m guessing that they were both apologizing for the trouble and attempting to offset any difference in cost I’d incur by trying to book something so close to our arrival date. In the 6 months instance, Airbnb did not step-in to offer any credits. This is more akin to their official policy.

Even if you delay your Airbnb bookings until a few months out, you still need to remain flexible. If you insist on trying to find and book a one-night stay in any given area, you may unknowingly be artificially restricting your Airbnb options. This is because many Airbnb hosts require guests to stay longer than one night. I imagine this is mainly used to reduce the effort involved in checking-in, checking-out, and cleaning in-between each set of guests. If you find your choice of Airbnb listings limited, consider adding a night to your stay.

In a similar, but opposite, vein, individual Airbnbs can easily get knocked out of contention from your searches if you fixate on long, contiguous date ranges. Remember, these are individually owned and managed properties, not cookie-cutter rooms in a big block of hotel inventory. If one night of your multi-night stay is already accounted-for in an Airbnb’s booking calendar, that (possibly otherwise perfect) Airbnb is not going to show up in your search results. As before, if you find your choice of Airbnb listings limited, consider shortening or splitting up your date range.

We once stayed at an Airbnb in New Orleans, Louisiana. Unintentionally (and unfortunately), the first night of our stay overlapped with the last day of Jazz Fest. Lots of people travel to New Orleans for Jazz Fest. As such, I had a very difficult time finding a good, reasonably-priced Airbnb for the entirety of our stay. What I ended up doing was booking two Airbnbs, instead.

We spent the first night of our stay at one Airbnb, and the rest of our stay at a second. The first-night Airbnb wasn’t my first choice, whereas the second Airbnb was. However, my first-choice Airbnb was unavailable for the first night of our stay. While it was inconvenient to transfer between Airbnbs during our stay, we're very glad that we did. My first-choice Airbnb was enough of an improvement over the first-night Airbnb to be worth the hassle.


The information I’ve provided you here has been hard-won through 3+ dozen Airbnb stays over the course of 6 years, starting with our first booking in 2012. Those stays have been spread across the United States, Caribbean, and Europe. All of the guidelines I’ve provided above are based on the knowledge accrued from those bookings. But, please remember that these are only guidelines - not rules. Guidelines are meant to flex and steer you in the right direction, not dictate your exact footsteps.

With every guideline I’ve provided, you will inevitably find exceptions. Truth be told, I, myself have probably experienced my own exceptions to each and every one. Consider these as starting points from which to begin your efforts. As you gain familiarity and experience with Airbnb, you’ll be able to better make your own judgments. With Airbnb, experimentation and flexibility are your friends. That won’t change, regardless of how many Airbnbs you have under your belt.

Aside from the always-unpredictable human aspect thrust upon you by each unique host, there’s also the fact that the Airbnb platform, itself, is still rather young and is continually changing. Even as I’ve worked to write this article, I’ve noticed new (to me) wrinkles with the Airbnb site. New features will be added that will obviate these guidelines. The tendencies and natures of both the hosts and guests will change. The snapshot in time to which these guidelines speak will pass. And you, the prospective guest, will need to adjust. Hopefully, you’ll find some enjoyment in that. If not, Airbnb might not be for you.

When approaching Airbnb, you should try to understand your own motives behind using it. For me, those motives are two-fold - saving money and connecting locally. Sometimes, with any individual Airbnb stay, I meet both of these goals. Other times, I only meet one. Regardless, for the past 6 years, the possibility of meeting those goals has been worth following all of the effortful guidelines I’ve explained here.

Yes, it can be tiresome having to analyze for “assumed”, “missing” , and “bonus” amenities. Yes, it can be exhausting to scrutinize each listing’s description, photos, and guest reviews. Yes, it can be frustrating having to sniff out the nature of each Airbnb and the host’s motivations. Yes, it can be maddening having to fiddle and experiment with your desired dates. Yes, it can be confounding not to have a simple and straight-forward set of instructions to follow when attempting all of this.

And yet, given the right motivations, the payoff can be well worth it. We’ve had us some wonderful experiences because of Airbnb. We’ve met some charming, interesting, friendly, memorable hosts. Absent that, we’ve saved significant money by staying at Airbnbs in some wonderful locations, which has, in turn, allowed us to travel to said wonderful locations. Regardless of which goal satisfied, our lives have been made richer because of the experiences made possible by Airbnb. If that richness comes at the price of some mental gymnastics or virtual sweat equity, I’m OK with that trade. If you are, too, maybe what you’ve been needing to get started with Airbnb is some advice. If so, please consider this your guide, tutorial, how-to, etc. Now, go sign-up with Airbnb!

All of the Airbnb links above are referral links. If you sign-up with Airbnb via those links, you’ll receive a travel credit at sign-up time and I’ll receive a credit upon completion of your first trip. If, for some reason, you’d rather not see those credits accrued, you can simply go to https://www.airbnb.com