Ever since I started working at Airbnb (I am no longer there after three years of fun adventures) people have been asking me for my favorite Airbnbs.  I don’t have any  mostly because they change constantly and because it depends why I’m traveling.  So in response to these requests, rather than providing specific listings I would give advice on how to find a perfect Airbnb.  And since people continue to ask, I thought it may be helpful to put these tips and tricks on paper.  A quick note:  be prepared for a longer read only useful if you’re planning your next vacation!

A few disclaimers first:

1. I no longer work for Airbnb but I still truly believe in its product. Throughout my years there I focused exclusively on hosts including helping them become better hosts.
2. I stay not only at Airbnbs, but also use other platforms including booking.com, homeaway.com / VRBO.com (same company) as well as hotels and resorts.  I’ve included my brief thoughts on these as well.
3. I have stayed at over 60 Airbnbs of all sorts – from Luxe to shared accommodations. As part of my work I have seen many more Airbnbs, have spoken with hundreds of hosts and guests to understand some of the main joys and fears of traveling using Airbnbs and other platforms.  I travel by myself, for business, as part of large groups, or with my family.
4. I have mostly had great stays, some absolutely incredible ones that could never be replicated in a hotel, and very few that I could do without.
5. I am also a host myself.

And with all that, I am still no expert.  Finding your perfect holiday home is a deeply personal endeavor, one that is based on what is important to you on a given trip, not what anyone else fancies.  It’s very possible that homes I consider gems could make your skin crawl.

Generally, unfortunately as a guest it requires some effort to find the perfect Airbnb.  As Airbnb gets smarter it may get to the point where it will know exactly what I want down to 3-5 properties each time I search, however, at the moment it’s pretty far from that.   It has made some progress with programs like Plus or Luxe, but these have major limitations still.  So, until then, there is some correlation between the number of minutes / hours spent on research and the outcome of enjoying your vacation in something beautiful.  Hence the length of this post corresponds to the number of steps necessary to succeed.  But don’t despair! This can be a fun hobby – you get to see new home designs, get ideas, and become an expert review-reader.  All as a bonus to planning a perfect vacation.

Here is how I find and book my perfect Airbnb:

Know why you’re going on a trip.  There are many reasons we need a place to crash – from once-in-a-lifetime dream vacation to a quick business trip to Chicago and everything in between.  Understanding why you are going on a trip will help you set out the criteria that are essential to narrow your search.  These are likely different for each stay.  For example, is it low price, or location, or having baby gates, or nice sheets and towels or staying in a really unique place that will make you most happy on this particular trip?  Figure out your criteria early on to help narrow the search later.

As you are beginning your search, it’s also important to note that Airbnbs may not always be ideal for each trip, but I always start with an assumption that it will be my best bet. It can be amazing for almost all trip types.  It’s great for family or big groups because having a kitchen and some space for kids to run around or share a bottle of wine with friends is critical.  It’s fun for business trips particularly if you want to be working as a team, or if your trip is longer and you want to feel more at home.   If you’re on your own, it’s great to stay in a shared space where a host can show you around and make you feel more like you belong in a new city.   Yes, sometimes you want to experience that just-opened boutique hotel or need water slides and big pools, but for me, with a few exceptions, Airbnb is usually where I end up.

Decide on the location. By location, I mean specific location within the city, town, resort, village and so on that you want to be – not which city or which village.  I make a big assumption that you already know where you want to go – e.g. you are not looking to get inspired for a destination for your family vacation.  If that is not the case, Airbnb is not the right place to start your search – it provides limited inspiration, details about a destination, what to do there, etc. (some of that content is there, to be sure, but nearly impossible to find at the start of your search).   So once you’ve decided exactly where you’re heading, you need to zero in on location – for example, specific neighborhood, or beach, or ski lift. This requires some work if you don’t know the place, which is usually the case.  Do you want to stay in town or on the outskirts?  On the beach or off the beach to save some money?  Close to major landmarks or somewhere secluded to have the time and space to write your latest novel? 

When we were recently traveling to Futaleufu, Chile, as a part of an extended trip, I wanted to be pretty remote.  Rob was booking this trip and first he looked at the map of Futaleufu, a town neither of us had ever been to, and expanded the search to look outside of town, while still searching for something unique.  This place seemed far enough from town, but still within reach.

And, it was beautifully modern, perched on an edge overlooking a lake.  He booked it without realizing that the only way to get to and from the house was via a private boat which turned out to be a spectacular surprise once we arrived.

To find these types of locations, I start every search by using the map function on Airbnb even when I don’t yet know the destination well and I’m still thinking about whether to stay at a hotel or an Airbnb.  More often than not I also have the booking.com site open and google maps as it provides access to hotels and all other alternative accommodations (though booking.com alternative accommodations listings are fewer, and I believe often of lower quality than Airbnbs).  I play around for a few moments to get the ‘lay of the land’, begin to understand pricing, and the types of accommodations that are available in my specific spot.

Start narrowing the search by using filters.  Once you’ve decided on location and that Airbnb is the way to go, get friendly with the filtering function based on the initial criteria that you’ve originally defined. Admittedly, Airbnb has a lot of work to do here as well.  For example, it’s impossible for me to filter on whether a house in directly on the beach or not, and that matters. Often hosts don’t fill in all the information about their listings so if too many filters are used, Airbnb removes all listings that don’t match exactly, even though some may but the information is simply missing.  So use filters sparingly.  

Even though the filtering is quite basic, it will limit the no. of listings considerably if the initial result returned too many options. There are some filters that are worth highlighting:

1. Home type:  Airbnb has just expanded this category to include ‘Hotel Room’, but traditionally there were three options: Entire Place, Shared Room or Private room.  I have never used ‘Shared Room’ however, I love the ‘Private Room’ option which is usually more economical and often surprisingly a comfortable way to travel.  We’ve done it as a family when a host has a few extra rooms and we’re looking for a quick place to crash or on my own when I did not want to actually stay on my own.  Generally though, we nearly always choose ‘Entire Place’ as we want full access and privacy wherever we’re staying.  I have played around with the ‘Hotel Room’ option a bit and at the moment I’m uncertain that it would provide what I need – it’s unclear what is actually included in the category (hostels? / apartments?) and I have not seen many beautiful and small boutique hotel rooms which is what I would prefer.
2. Superhost:  When in doubt or to narrow the search, use this filter as you are much more likely to be satisfied with the home you find.  Superhosts are only the best of the best hosts on Airbnb – those who provide excellent hospitality,  don’t cancel, and have outstanding reviews.  I sometimes choose to stay with a superhost even in a shared listing.  We arrived in Puerto Varas in Chile at this hosts’ home and found out that she had a horse as a pet!  There were chickens and roosters, dogs and turtles and the kids loved it.  She was lovely herself hosting some other friends for the evening and we stayed up late exchanging stories and drinking Chilean wine.  It was a perfect lay-over spot to get to know the area more.  To be sure, the Superhost filter has to be used sparingly as well.  Many incredible hosts on the platform don’t qualify for super host status for a variety of reasons, so you may miss some great listings by turning it on too quickly.  Also – those homes that are professionally managed often are not managed by ‘super hosts’ yet prove to be excellent homes, particularly in vacation rental destinations like beach and ski.
3. PLUS listings: In a few urban destination now, worldwide, you can now search for PLUS listings.  It’s hard to go wrong by booking a PLUS property – it’s been vetted in person by someone from Airbnb to ensure that it’s well stocked, well designed, and well taken care of.  The main issue is that there are so very few properties that are PLUS, but it does not hurt to check if they exist in your destination.
4. LUXE:  It’s taken Airbnb over two years to begin integrating the listings from its Luxury Retreats acquisition, but some results are starting to show.  In a a few destinations wordwide you can go really high-end (or if all else fails, go directly to LuxuryRetreats).  These listings tend to be beautifully designed and come with full staff – usually someone can stock your fridge, cook all the meals for you, and likely babysit too.  It’s particularly nice when traveling with a family to a beach destination, for example.  You can spend more time playing at your own pool while the staff does most of the work for you (cleaning, cooking, laundry).  The challenge though is similar to that with PLUS – very limited inventory and very few destinations have Luxe properties.

Put in the time with the reviews.  Airbnb also has a lot of work to do here.  Nearly all homes are rated 4+ which does not help you to narrow your choices.  It’s also unclear who left the review (was it another family or a group of college kids?), what was their purpose of the trip, and which part of the entire trip worked or didn’t.  Which leads to the biggest piece of work – unfortunately the only way to really get to know a home is by actually taking the time to read the reviews, learning to understand the language between the lines, and looking out for what you want specifically. 

The couple of times when my experience was one I wouldn’t want to repeat, I did not take the time to fully read all the reviews.  In one instance at this Airbnb my family arrived with our friends to Tahoe and the house turned out to be right on the main road, extremely busy, and rather loud from street noise.  I went back to look at the listing and it turned out that only the fourth review mentioned something about the busy road, and a few others after, but I hadn’t gone as far to read them all.  Nor did I really look at the map.  I felt too comfortable too quickly because it was a Superhost. The listing description did mention something about the road or being across from Lake Tahoe, but again, I didn’t get to it.  It was my fault, but still – I hope Airbnb will do better in the future.  It’s all about managing expectations and in this case, my expectations were much different than the reality.

Look for other details.  There are many details in each listing that provide a lot of hints about the quality of your stay:

1. Professionally managed listings: Homes that are professionally managed, meaning that the host is managing 6 or more properties (which you can tell by numerous things, including the picture of the host – sometimes it’s a company logo, or simply click on the host and see how many properties are managed by that host) – tend to be much more consistent.  Usually, but not always, the company understands hospitality well and is willing to ensure that the place is well stocked, maintained, clean, etc.  Traditionally, it has been much easier to find these types of properties in sun and ski / traditional vacation rental destinations, but we are starting to see these exist in urban destinations as well because of companies like Vacasa, Sonder, StayAlfred, Oasis, and several others, though inventory is still quite limited relatively speaking.
2. Price:  Airbnb is a marketplace like any other.  If there are hundreds of properties in a given location, they are likely priced at market as savvy hosts understand pricing and price accordingly – so you get what you pay for.  In some markets, however, strong price arbitrage is evident particularly if only a few properties are listed.  If price is an important factor, keep searching as you can find gems priced reasonably low.  This is particularly true for new listings, especially those that don’t yet have many reviews.  You’re playing with luck, but more often than not it can be worth a risk, particularly for a shorter stay.  This listing in on the island of Chiloe, Chile is a perfect example of how some homes provide amazing value – we were close to a beach, had beautiful sunsets every night and a perfect home.
3. Photos:  The pictures almost always tell 90% the story.  There have been many times that the place turned out to be better than the photos (this Airbnb in France was outstanding and the pics don’t come close to capturing its charm), but usually if you do not like what you see, don’t book.   There are a few hints that could speed up the process when flipping through photos:
   1. Quality of the photography:  poorly lit photos, super-wide angle photos, those with poor angles and clearly taken in a rush with an iPhone are likely a bigger indicator that the host has not taken the time to merchandise their listing, and may also not take the time to maintain it well.  It’s not always the case, but if there are other options, why stay here?
   2. Bed covers: I wish all hosts were willing to invest in white sheets and duvet covers.  They could charge more and life would be simpler.  But most don’t.  The ones who do are clear winners so if you see white linens, you’ve likely found a nicer place than most.
   3. TVs: Hosts still often have the big box TVs in their listings (particularly outside of the US).  It’s not that I mind the TV itself – I usually don’t watch it – it’s just that it tells me that they’ve not updated anything since early 2000s.  Not acceptable.
   4. Furniture:  If it looks torn and used, it’s another sign that well, there is not much love that has been put into the place.  See plastic chairs outside?  Probably not your best home.  It’s not always the case, but I’m always weary when I see this.
   5. Bathroom / kitchen photos: These tell most of the story.  Pay attention how nice they look and whether you would want to spend any time in these spaces.
4. Length of the description:  Some hosts will write four sentences and be done.  Again, it doesn’t mean that the place is not going to work, but if the host is not willing to sell their place, I tend to worry about how little work was done to the actual listing to make it comfortable for me.  Skip these listings.

Narrow down the list to 2-3 listings and reach out to the host.  After some homework, hopefully 2-3 listings will stand out above the rest given the criteria that you set out in your initial search. I then contact the host for all of the ‘short listed’ properties (btw, I do use the list function on Airbnb which helps me to save properties that are in the running).  I do sometimes use instant book (very short stay / low risk) but generally speaking I prefer to start getting to know the host.  I send a quick note to introduce myself, tell them why I’m coming, and ask to ensure that there is enough space for all of us.  Oftentimes I may have specific questions based on pictures or previous reviews which I will ask at that point as well.  I use this process to see how helpful the host is – usually it’s a good prediction of how responsive they will be once we arrive.  Do they answer quickly?  Do they actually answer the question?  What is their tone?

Book your trip. Based on this final step, it usually becomes clear where to stay.  By the time I hit “book”, I have the confidence that I’m going to be staying with one of the thousands and thousands of Airbnb hosts who are amazing.  Often the host will go the extra mile to make my stay even more comfortable:  book my babysitter, all of our excursions, provide additional information and so on.  Or maybe I won’t even meet them, but that’s what I want for the type of trip I’m taking.  Either way,  I’ve already begun to build a bit of trust with the host before I arrive.

As we end, I wanted to mention a few of the other platforms including booking.com / homaway / google.  It’s worth understanding the benefits of booking on these platforms over Airbnb, and although there aren’t many, some merit serious consideration.  First, if I’m looking for a hotel, I will often work on google / booking.com  (but more than likely book directly with the hotel as from my years at Expedia I know that booking directly at best may come with some benefits, and at worst will come with no surprises while this is not always the case when using booking engines).  If I am looking for something more alternative, I can still search booking.com because in some regions of the world (Africa, Europe) they continue to maintain a strong share and have many legacy listings that have not yet moved to Airbnb.  Some hosts cross list – it’s more likely that a booking.com listing is on Airbnb than the other way around.  If the same listing is on both platforms,  it is sometimes cheaper on booking.com because the commission structure is different on both platforms and not all hosts adjust to make the final price equal to the consumer.  Also, the cancellation policies are usually more forgiving on booking.com and if I’m not 100% sure of my timing or itinerary I may choose not book on Airbnb to avoid any cancellation fees later.

You’re an expert now!  If you’re still curious, below is my process for booking this great listing in Chiang Mai, Thailand.  Otherwise, start searching and have fun!

We were going with a bunch of friends to Chiang Mai, Thailand and I was under pressure to find a perfect home for 10 of us.  I wanted a home that would be comfortable, modern, with a pool.  A view would be a plus.  I first looked around Chiang Mai and quickly realized that the bigger homes, ones that we needed, were more likely outside of town.  I wanted all of us to stay together so getting four hotel rooms did not seem appealing with toddlers running around.  Using the pool filter returned over 20 results for Chiang so I clicked Superhost to narrow the search.  There were not that many that included both a pool and enough space for all of us.  I looked at pictures and found some amazing homes.  I started reading reviews and it became clear that a couple of the hosts were exceptional.  They cooked all meals and helped to arrange all excursions.  I emailed a couple and quickly made my decision.  Joy and her husband turned out to be incredible hosts throughout our stay and there is no way we could have had a similar experience at a hotel.  See the pic below of our first evening there:

Happy Travels!