The Time-Based Approach to Finding and Booking Accommodations

Is it a hotel? A resort? A condo? Who knows! That's the point.

Finding a place to stay in is more straightforward than it might seem.

I do it based on time spent in a place, as that determines the type of accommodations I get.

Short Stays

If I’m looking to stay between 1-2 weeks, sometimes up to 3 (but for me that’s pushing it), I’ll book a hotel.

I usually use either Hotels.com or Agoda.com, depending on the city. Booking.com is also popular, but I don’t like using their website, though their App is quite good.

Hotels are such a commodity, so similar, and usually with so much availability, that it’s best to not spend much time, just plug in the prices and location (I use map view) and start there.

A Treatise on the Uses & Uselessness of Filters

The problem with filters beyond those basic ones is that hotels often don’t fill them in properly, so you can miss out on some places that actually fit your criteria – but if you have too many options at your price point, give the other filters a try and see if you can’t just find one to pull the trigger on right away.

Then, just request the extra stuff that’s room-specific in the comments – I like asking for a high floor, away from the elevator, away from the streets, in that order, as a minimum.

When asking for specific accommodations like this, remember to say “please” and to thank the staff – it can really go a long way.

Pro Tip: Finding Hidden, Better-Than-Advertised Hotel Rooms & Suites

One other quick tip for higher-but-not-yet-high budgets is that you can often get a higher quality of room (e.g. a nice big suite) at not as great (but still good and by no means anywhere close to shabby) hotel, at the same price or less than a standard room at a higher star hotel.

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The problem is that you have to look for it within the listing, as usually it’s just the cheapest room advertised, so it takes time – up to you if you or your VA’s time is worth it – but a way to shortcut it is to only check in larger hotels (which you can usually either tell from the styling of the room or if they have a picture of the hotel among the first few).

Medium-Length Stays

For more than 3-4 weeks, I almost exclusively go for an Airbnb.

This is because they typically have:

  • much more space,
  • better interior amenities (building amenities are a different story, but the most important of those you can usually get better versions of externally anyway),
  • larger fridge,
  • a full kitchen,
  • (often) faster wifi,
  • less chance of noisy neighbors (due to fewer neighbors)

…To name a few.

I don’t use any other site, though some people do use VRBO, Flipkey, and other such sites; Airbnb usually has more than sufficient availability (especially if booking early), but these are good backups in case you can’t find what you’re looking for.

After about the 2 month mark, I’ll start to explore other longer-term options.

Long-Term Stays

If I’m only in a place for 2 months, I’ll maybe flip a coin mentally, but it’s a weighted coin and generally lands on “just rent the airbnb for 2 months”. Sometimes this means switching airbnb’s due to availability issues (even at higher prices – the dreaded “I’d book you for 2 months but somebody has 1 weekend right in the middle of it”), but if it’s just 2 months I’m staying, I take it as a good opportunity to get to better know a different area of the city, even if it’s still close by. Although I generally try to avoid this, I usually only encounter it if I book too close to the dates I’m planning to travel, but it can be a good opportunity if you happened to pick an area you turned out not to like.

Beyond that 2 month mark, though, I start to look for longer-term options based on how long I’ll be staying – which if it’s more than 2 months, usually means I like the place, and will generally be 3-6 months depending on multiple factors (seasons being one of the big ones).

This is better done with a local agent (although agents often deal in the realm of the “normal” year-long rental minimum, but if you’re visiting a very touristy place there may be more short-term or seasonal rentals), or by yourself.

Local Agents

Back in the day before Airbnb’s were globally plentiful – heh “in the old days”, less than a decade ago – I would just go to the area I was interested in living in (obviously 10 miles uphill both ways) and look for rental signs, talk with agents who set up shop in the area, and go into the nicer buildings or complexes I wanted and ask the reception if there are any units for rent or otherwise who to talk to about them.

Especially in tourist destinations where they’re used to short-term travelers, this is still a great option. In fact, I recently just got an oceanside condo on a month-to-month basis (which I later found out was also on Airbnb – at a much higher cost) from one of the first buildings I went into.

This may seem tedious, but when I do it (which is rarely), I use it as an exercise in exploring the city.

Either I’ll already be exploring and happen across a place that fits my criteria and go in and ask (which is usually the case) as I’m passing by, or I’ll make a morning or a day of it, again under the umbrella of exploring while talking to locals. It’s a great excuse for that.

Local Listing Sites

Alternatively, in these modern times, the young whippersnappers have invented local listing sites (many before Airbnb … but I digress), which is the other place to do this kind of searching from the comfort of your initial hotel/Airbnb (and/or your VA’s home) – either real-estate (sometimes rental, and sometimes short-term-rental)-specific ones, or general ones with rental sections (think Craigslist, but usually either country and/or region specific).

Getting Better Airbnb Rates

Sometimes your Airbnb host may be open to negotiating a favorable long-term pricing for you. The best parts are:

  1. They’re already used to short-term rentals, which that flexibility can be really helpful, even if you’re still paying a premium over a yearly or longer contract (naturally – that’s the “traveler toll” and you’ve got to get used to it in this lifestyle), and
  2. You’re already used to, and like, the place – and are already there (so no moving!)

Whichever way you choose, make sure you do it with plenty of time in advance – as soon as you know you’re staying longer, make it a priority – both in order to find the best availability (early bird gets the good view), and so you’re not running around and stressing near the end of your initial arrangements.

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Inside this frequently-updated report, you'll find the direct, to-the-point answers to the most commonly asked questions about long-term & full-time traveling.

Enter your name & email to get your free copy - and learn how you can get your own top questions answered (for free!) as well.