



This huge duplex condo in the historical center of Salvador, Brazil with a private pool and killer ocean views cost me under $100
I’m sorry for the radio silence lately. Between my short vacation in the DR and having been working on a big project, I’ve found myself out of breath. I do have several posts in the queue and will resume my normal regimen of 2-3 posts weekly shortly. My apologies for not putting out some stuff in between, but you know how I like writing filler posts (I don’t).
I’ve wanted to write about Airbnb and the vacation rental market in general forever, but have been delaying it because I knew it would be a huge job. How did I know? A few years ago, a company called FlipKey asked me to do a post on vacation rentals. And instead of writing one post it took me two – just to be thorough.
Vacation Rentals Pros, Cons, Savings, and Trade Offs: Intro
Vacation Rentals Pros, Cons, Savings, and Trade Offs | Case Study: Paris
So, this is a mammoth post. I thought of making a series, but decided against it. If I was reading a post named the “Airbnb success tips,” I know I’d like to have this stuff in one place, and maybe you would too. So … please be patient.
No, Airbnb did NOT give birth to a new industry
I’ve been in love with vacation rentals forever. So many people believe that Airbnb single-handedly created a brand-new industry, it’s not even funny! Airbnb just did to vacation rentals what Netscape (remember that name?) did to the Internet – it made a more-or-less cottage industry accessible to the general public.
I started using vacation home rentals back in the 90s, before any owners would even think about taking credit cards. I looked for ads in newspapers and newsletters, contacted the owners and negotiated the terms because I noticed that I was often able to rent a large house or an apartment for less than a simple hotel room would cost. That changed the way I approached budget travel.
I had a tight circle of friends those days, and when we all pitched in, it would often cost us peanuts. Once we rented a luxurious 4-bedroom villa in Kissimmee, FL with a large indoor/outdoor pool and huge Jacuzzi for about $25 per person per day. To save on the airfare, we drove there in a one-way rental van. Oh, good and innocent pre-credit-card days of nearly free travel!
Of course, in most cases, you would have to mail the host a check to secure your reservation. I have to admit, it was nerve-racking, but I’ve never been burned.
Why bother with Airbnb? Why not just stay at a hotel?

This is an Airbnb picture of a gorgeous villa in Buzios, Brazil. We stayed there about 10 years ago, but unfortunately, I lost my photos of that gorgeous, luxury 3-bedroom villa with million dollar views and a pool that we rented for $150 a day.
People have different vacation goals. You might value full service and better predictability more than space, or you might find a fantastic hotel deal, or you’re flush with points, or your goal is to stay at an aspirational destination resort – it’s not like you don’t have a choice.
However, even if you’re a hotel kind of guy or gal, you might still be better off using vacation rentals sometimes. Here are a few factors that might push you in that direction.
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Big family or large company gathering
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Budget constraints
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Certain unique features you can only find in some homes (unique homes are more common than unique hotels)
To me, however, the most important consideration is value. You simply get more value (space) for your buck compared to a hotel room. I almost never use room service. I certainly don’t need a minibar. And many buildings and private homes/villas offer extra amenities like a pool, or hot tub. Even when I have enough hotel points to stay in town for free, I often opt for a vacation rental – imagine that!
That I mostly fly solo or with one travel companion and still stay at vacation rentals must tell you something. When you’re traveling with a large family or a group of friends, this is a no-brainer, IMHO.
Airbnb is not the only game in town
There are literally thousands of companies that rent out vacation homes, but don’t get fooled by sheer numbers – many of them are already on Airbnb.
There are also owners and management companies that rent their properties on several platforms, and this is where you might want to put on your travel hacker hat because they might price their homes differently. I once saved about $40 a day on a fabulous pool duplex apartment in Salvador, Bahia by renting it on Booking.com rather than Airbnb. Other times Airbnb is cheaper. You just need to check.
After decades of mergers and acquisitions, it may not always be easy to figure out which companies are independent and which are the parts of bigger conglomerates, but here are the largest companies you might want to check before making a decision.
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Booking.com – start there. This is the closest competitor to Airbnb, with 5 million listings.
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HomeAway/VRBO – acquired by Expedia in 2015. 2 million listings each (I believe they feature the same properties).
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Expedia Vacation Rentals – 1 million listings
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Trip Advisor Rentals – 830,000 listings
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FlipKey (a part of Trip Advisor, but listings may differ) – 300,000
There are many more than these, but seriously, how far do you want to take it?
I would at least compare your Airbnb findings to Booking.com and HomeAway/VRBO. You will often find the same properties on those platforms that may be differently priced. If, however, the price is the same or the difference is negligible, I recommend Airbnb, and here is why.
Airbnb is sleeker, easier, and more user-friendly

On Easter Island we rented a 1-bedroom apartment with a huge veranda for $50 a day. It was a decent and well-equipped place with nice and hospitable hosts who invited us and other guests for a BBQ one day
There is a good reason why Airbnb has become so popular (aside from the amazing business acumen of its founders and their questionable marketing techniques).
Airbnb is easy. Very easy. Almost too easy if you ask me.
That ease of use is a double-edged sword. People often book their vacation home rentals as they would book a hotel – point and click. They neglect using an important Airbnb feature that allows them to contact the host and ask questions.
You don’t have that option on hotel booking sites. You do, however, have this option at Airbnb.
Asking questions is extremely important. You’re staying at someone’s home. Pictures NEVER tell you the whole story.
Increase your Airbnb success rate with my SRA strategy
SEE the brief description and the pictures. Check the number of review stars the property has gotten and more importantly – the number of reviews. A 5-star house that’s been reviewed 3 times is always less than ideal. It can be perfectly fine, but I try to avoid new listings. If there are not enough reviews, I’d usually move on to another property just to be safe, but there might be a workaround or two (more about that a little later).
READ EVERYTHING! Seriously, do that. When you find a home you really like, read the description (again), all the policies, and every review you can find. Find whatever negative information you can that’s important to you and make a note. Then investigate them some more.
ASK the host any and all questions you have. Try to start off the conversation by saying how the host’s property has caught your eye (if listed by the owner). Remember that these people are not hospitality professionals. And even if they were, a little flattery can go a long way.
What if you love the place, but there are no or very few reviews?
I love to be safe rather than sorry, so I normally want someone else to take a test drive first and tell me how they felt. However, renting a home new to the site has its advantages.
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You often get a brand-new or recently renovated place
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The owner might bend over backward to please you
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It’s usually cheaper than a comparable vacation rental
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When it’s not, the owner might be more receptive to your counter-offer in exchange for your detailed review
In addition, there are a couple of other things that can help. If the host is not the owner, but just manages the place, you can click on his or her tiny photo and read the reviews of their other properties. Take a look at this profile, for example.
As you can see, this host is a Superhost (later about superhosts) and has 107 reviews for other properties. Superhosts are supposed to have at least 4.8 overall rating, and I think I’d be fine. Does it mean you shouldn’t read these reviews or not ask questions? No it does not!
Just for the records: I don’t know this particular host from Adam and have no knowledge or opinion about her services, but dealing with a Superhost gives you an extra shot at getting an uninterrupted and enjoyable vacation. Does it guarantee anything? Not at all!
So should you trust these reviews?
The simple answer to this question is no! Not totally. And yet, these reviews are still an invaluable tool.
People’s minds are a funny thing. Some folks are simply timid and will go to great lengths to try and avoid doing anything that might offend another person. Other people are impossible to please and very vocal, no matter what you do for them.
You shouldn’t trust any review 100%. Good or bad.
Here is a vivid example. Note that this listing has 254 mostly 5-star reviews!
Would you be renting from these “young professionals” if you read this review? Not likely, right? The problem is if you only look at the number of stars and only read the first few reviews, like most people do unfortunately, you won’t see this exchange because it’s not on the first page. Which is why it’s so important to sift through all the reviews in order to get the most objective picture of your future vacation home.
By the way, do you know who those “young professionals” are? That’s right: a Superhost!
So, yeah, take everything with a grain of salt, and you’ll be fine.
The anatomy of a good review
That was an extreme example, of course. Hosts don’t usually scream at people who leave them reviews they don’t like, although it does happen. More often you try and read between the lines to get some tidbits about the place when the owner is not 100% forthcoming, and no one is forthcoming 100%. People can squeeze in the information you need to know even in a glowing review. Take a look at this one, for example.
Let me first say that Dagmar was responsive and generally a lovely and accommodating hostess who has lived in Berlin for 30 years. The small efficiency apartment was very clean and had everything we needed for our two night stay in Berlin. The area, Charlottenburg, was wonderful, safe and we were very close to the S-Bahn that took us right into Central Berlin. We also used taxis, as needed, but they were a little pricey. All of the cafes literally in front of the apartment were very good. The apartment itself was small, pretty much just one room with a private entrance from Dagmar’s apartment. It did have a full private bathroom with shower. Be mindful that there are four flights of old stairs to climb (not ideal, but not impossible) and there is no air conditioning in the room. It got quite warm, but with the windows open at night, it wasn’t too bad. Dagmar also allowed us to store our luggage for the day of checkout as our flight wasnt until later that evening. Overall, for the value, we would recommend this room!
See what the reviewer did? She gave the host a good review but sprinkled it with precious tidbits of information you really need to know. You might still be willing to book this apartment, but there will be fewer nasty surprises when you arrive.
Here is a good article: How to Decode an Airbnb Review
In 2018, Airbnb started Airbnb Plus Verified listings. These list upscale properties that have been verified in person by Airbnb staff. These homes cost more than comparable properties, but you’re getting some extra peace of mind.
Airbnb search parameters
Airbnb has a relatively simple and user-friendly interface. It lists major features and gives you a lot of control in executing your search. Here are the major parameters you can set.
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Dates (set if you’re not flexible, otherwise leave open or you won’t see all properties)
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Guests (don’t lie or you might set yourself up for a disaster)
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Work trip (ignore even for a work trip)
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Type of place (do yourself a favor and choose “Entire place”)*
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Price (very important: chose a realistic price range with a little extra on top if you’re willing to negotiate)
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Instant Book (ignore)**
* Airbnb success tips: always rent the whole place rather than a room with the host in the apartment. Unless, I don’t know, he or she is cute. Whatever savings you think you’re getting, roommating on vacation is rarely great fun.
** Airbnb success tips: Besides the obvious fact that you must ask questions, Instant hosts can cancel a reservation without a penalty if they’re “uncomfortable” with the guest, and that may mean a lot of things. If anything, be more careful with such hosts because you won’t see the automatic cancellation messages in their reviews (more info in the section “The host canceled this reservation … days before arrival. This is an automated posting”)
And then there are more settings in the “More filters” tab
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Beds
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Bedrooms
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Bathrooms
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Verified Places (if you decide to go for Airbnb Plus or Airbnb Luxe for extra piece of mind)
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Superhosts (I’d ignore, but it’s up to you)
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Accessibility
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Amenities
AIRBNB AMENITIES
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Facilities (depending on your destinations, there can be more or fewer of those)
AIRBNB FACILITIES
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Property type (depending on your destinations, there can be more or fewer of those)
AIRBNB PROPERTY TYPE
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Neighborhoods
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Host Language (most lists English)
Quite impressive, right? Well, yes, you do have a lot of options to choose from, but are these parameters really all you need?
Hardly!
You can’t search Airbnb by a keyword!
And that sucks. A lot!
What if you must have ocean view (or any view for that matter)? Surely, the host will probably mention that in the listing, but why do you have to sift through dozens or hundreds of listings to find what you need? Remember, by the way, that ocean-front doesn’t mean ocean-view. Always verify whether you’re getting what you’re expecting to get.
Unfortunately, the view is not among your search parameters. And neither are other hugely important things.
What about beds? At the very least, tell me if they’re hard or soft! How many things are more important for a traveler than a good night’s sleep?
Have a pool? Great! Now is it private or shared? If you value privacy, it would help to set your search parameters so you can save yourself some time rather than sift through the listings. Unfortunately, at Airbnb it is what it is.
Furthermore, very few things annoy me as much as Airbnb hot tubs. So many hosts around the world claim ignorance when you ask them if they really have a hot tub (“sure, we have a tub and hot water”) that I’m really mad at Airbnb for not using clear definitions, either Jacuzzi or whirlpool. Seriously, how hard is that? If the listing claims that the house is equipped with a hot tub, but it’s not in the pictures or the description – ask. And while you’re at it, ask if it’s working too. You’d be surprised …
That question – if everything works – is an important one, and it’s simple, too. I always ask twice: before making a booking and right before the trip. You want to make sure that things are functional. The AC, the Internet; ask if there are issues with hot water, and whatever else might be important to you.
Here are some other things. What about the noise level? What about mosquitoes? Are these things important to you? Then ask. Hosts are likely to leave out any negative remarks in their listings, and you can’t always rely on the reviews.
Airbnb success tips: don’t neglect to ask about things that are crucial to you, EVEN IF they are listed in the description. I once noticed there was no sign of an air conditioner in the pictures even though it was listed. The owner then told me – not kidding – that he didn’t list an AC and had no idea how it’d gotten listed.
Take it easy when not everything goes your way
So, you’ve done your homework, you’ve asked every conceivable question, you’ve arrived, and yet, something is still rubbing you the wrong way. It can be anything. The kitchen lacks the exact thingy you need. The Internet is slower than you expected. The water takes forever to warm up. The AC isn’t cooling the room well enough. The floor is not barefoot-compliant – it can be everything and anything at all.
What do you do when you have an issue at a hotel? You call the front desk.
Let me say, right there, and I hope you agree, that your mileage may vary even at a good hotel. Imagine dealing with a host who might be physically located on another continent.
Just kidding. Don’t sweat it, really. Hosts are usually very responsive. Or they might have local managers, ready to assist. A bad review is a huge blow for a host. You do have this power over them – the power you don’t normally wield at a hotel. And yes, they can leave a review for you, too, but it won’t affect your livelihood. Now you know who is more concerned.
I’ve used vacation rentals dozens of times. Hiccups happen, but I don’t remember even one ruined vacation. Just take it easy, and cut your host a little slack when needed because …
Your Airbnb host is not a hospitality professional

Our $90 2-bedroom in Cartagena’s El Laquito was clean and nice, but nothing special — except for the views!
You can and should expect courtesy and a few smiles, but don’t expect your host to bend over for you. Hospitality is a tough business, and even a person working at a hotel may not be a real pro. Now imagine someone who’s doing it in her spare time (or worse, during regular work hours 🙂 ); who hasn’t received any training; and who, simply put, might be in over her head. Unless the host is arrogant, lazy, and unresponsive, I would cut them some slack.
And like I said, I’ve never met a host who would make me mad. Not because I’m so mellow, but because they’re really trying. But you need to realize another important thing. And I know it goes without saying, but sometimes we tend to forget a simple fact. Just like your host is usually not a professional …
You Airbnb is not a hotel!
There are Airbnb properties providing exceptional, 5-star customer service, but they are few and far between. You can usually (but not always) count on a small soap (maybe), a small bottle of shampoo (maybe), toilet paper, and a couple of towels. Since there is no room service, you can’t demand they replenish that stuff. Now, some hosts go above and beyond and leave you more towels, more soap, more shampoo, and more everything, but unless you see it in the description – always ask.
I usually ask about important things like towels before the booking, and also write to the host prior to the trip to figure what items I’m going to find in the apartment before I stock some supplies from the store. It tells them that I know the rules (not confusing their place with a full-service hotel) and maybe makes them more willing to do something extra for me. Or not, it really doesn’t matter.
As to soap and shampoo? Since we all stay at hotels sometimes, don’t neglect to pick a few “travel-sized” items from your hotel rooms. Don’t worry, they want you to, anyway.
Can you negotiate?

Our ridiculously luxurious 3-bedroom house with a private pool and Jacuzzi in Iguassu Falls was also ridiculously cheap — around $80 a night!
Yes, but there is a but coming.
First of all, there are 2 categories of hosts on Airbnb – the actual owners and managers who take care of multiple units. Only an actual host can offer you a considerable discount. Managers, in most cases, either aren’t authorized at all, or they might offer you a minuscule discount, like 5% or something.
A host can send you a discounted offer upon request. It doesn’t mean they will, but they have this option. However, the best if not the only way to bargain on Airbnb is to contact a host who owns (not manages) the place right before the trip. Keep in mind that very few hosts (unless they’re new and in dire need of reviews) will offer you a discount in advance since they still hope to get a full price for their rentals.
So, yes you can, but there are a few downsides to this approach.
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Best listings might be snatched by the time you start hunting
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You might have to choose from more expensive listings anyway, and
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Hosts that feel they’ve been taken advantage of might not be willing to provide better support during your stay
The first position in this list is the most important, and it’s a major reason why I rarely try to negotiate. Honestly, when I find a fairly priced listing I like – I just book my stay without trying to squeeze an extra buck or two out of it. However, I do bargain when I cut it too close and my trip falls within the next few days. How do I fare?
I’d call my success rate 50/50. You would think that every host would jump at an opportunity to fill their space even if at a reduced rate, but it’s not the case. Some hosts take it personally and don’t respond. Others refuse to do the discount, but approve me for the going rate (but I’m stubborn too, and when the host doesn’t play ball, I don’t either). Yet, the most reasonable hosts make a counter-offer. If it’s relatively close to what I’m willing to pay – I take it; if not – no harm done.
I’ve read some cavalier posts from folks claiming they’ve routinely gotten 50% off the listing price. I’m not saying these claims are “slightly” exaggerated, but if true, I don’t know how they do that. I’ve only once managed to get that kind of discount. In most cases, it’s 10%-25%. Seriously, when you’re asking 50% off, a lot of hosts will take it as a personal offense. You might try, but I wouldn’t.
When you do negotiate, please be respectful. Make no mistakes: hosts hate guests who try to bargain them down – just read what they say about it on their forums. I especially love this one, LOL:
It is very rarely okay to negotiate and as a host we usually reject anyone that asks based on bad past experiences. Just about every guest that has asked for a discount has turned out to be a bad guest so now we just steer clear of discount seekers in general.
You must soften the blow. Tell them why you love their place, point to positive reviews from the previous hosts if you have any, pledge to treat their place as your own (and do!) and promise to write an honest, detailed review (and do!).
That’s about it – not exactly rocket science.
“The host canceled this reservation … days before arrival. This is an automated posting”

This 3-bed, 3-bath villa with a private pool in Sanur cost me around $90 a night. A bit too spacious for one person, but I’m not complaining. 🙂
There are obviously some risks when you’re dealing with Airbnb, but there is one that really stands out. A host can cancel the reservation at any time prior to your arrival.
Now, before you start panicking, this happens very rarely. And it’s not like there are no penalties for this – there are (unless a host can claim extenuating circumstances). When a host cancels, this message posts automatically, and a host can’t undo it. When you read a review and see the language above more than once per – I don’t know – 50 reviews, run, don’t walk, especially if the host doesn’t explain what happened (hosts are allowed to write a public response and an explanation).
It’s not as if all cancellations are not legit – hosts are humans, too. People can get sick or indisposed, and there might be issues beyond anyone’s control, but those problems often arise due to scheduling conflicts. Since many Airbnb hosts list their homes on several platforms, and some of them have no idea what they’re doing, they simply forget to update their listings.
Let’s say a host wants to get as much business as she can, so she lists her property on Airbnb and Booking.com. She then gets a client on Booking.com, but forgets to update her Airbnb schedule. When someone books her home for the same dates on Airbnb, she has to cancel the reservation, and the preceding message appears among the reviews.
There are other penalties, too, but this message is the most severe one, which is why hosts won’t normally cancel on you unless they don’t have a choice.
Airbnb Success Tips: Try to book with Superhosts if their price is competitive. To be a Superhost, one must maintain less than 1% cancellation rate.
Superhosts cancel less than 1% of the time, not including extenuating circumstances. This means 0 cancellations for hosts with fewer than 100 reservations in a year. Rare cancellations mean peace of mind for guests.
Still, when it happens to you … a day or two before your arrival … and it’s a high season in an expensive city, and you’re traveling in a large group, a cancellation like this has all the signs of a catastrophe. If that happens, try not to panic, and contact Airbnb immediately. Be persistent. There are stories on the Internet about Airbnb picking up the costs of alternative accommodations, as well as stories of people who’ve been told to take a hike. Read your rights carefully.
As a reminder, never do Instant Bookings because Instant Hosts are exempt from the cancellation penalties.
Let’s recap
Using vacation rentals allows you (in most cases) to get a better bang for your buck. You’re normally getting more space, a kitchen that can cut your dining expenses, and your host can give you invaluable tips that can help you enjoy your stay even more. However, there are trade-offs. There is no room service, and when there is an issue, the help might not arrive immediately.
Even if you love staying at hotels or resorts, consider vacation rentals when you travel with a group of friends or extended family.
Airbnb has the most user-friendly interface on the market, although it comes with certain risks like the host’s ability to cancel the reservation at the last minute. They are not huge risks, though, and they can be further mitigated by choosing hosts with plenty of reviews and reading those reviews carefully.
I will write a separate post about using Airbnb for aspirational travel because, gee, this one is over 4,000 words already. It’s more like a White Paper than a blog post, but I’m not complaining. Hope, you’re not either.
Please share your own Airbnb (or any vacation rental) stories, good, bad, or ugly; and if you never use them, tell us why.






