A few tips for longer Airbnb stays (A Carrie commentary)

In a recent “Ask Us Anything, Live“, someone asked the following question:

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I have a question for Stephen and Carrie. Now that I am retired my wife and I are interested in finding rentals for several weeks at a time. I am pretty good at finding good properties on Airbnb and VRBO for several days but have less experience with navigating longer term rentals. Do you have any tips on how to find good locations and get good deals?

Since the second phase of my nomad life was a slower, more Airbnb-centric travel style, I thought this would be a good question to address a little more thoroughly.

After years of traveling nomadically on miles and points in the 2010’s, I essentially retired from the points and miles game to focus on other things, (yes, despite working for arguably the best points and miles blog in the space). Now, I’m trying to gradually re-enter this world, this time learning the tricks for myself instead of coasting along as a P2. This series chronicles that experience along with occasional memories from nomad life. If you have ideas for topics you’d like me to cover, please comment below!

How do you find good short-term rental locations?

Airbnb map

When I’m visiting someplace brand new to me, I do just a little research to try to establish which part of town might be considered either the old town or the arts district. I highly value walkability, in part to prevent the need for a car rental if I’m otherwise stationary for a stretch of time, and in part because meandering is one of my favorite activities. Once I figure out where that part of town is, I do a search for coffee shops, parks, restaurants, and grocery stores in that neighborhood. Those are the places I’m most likely to want to walk to, after all.

I also sometimes look up art galleries and yoga studios, not because I think I’ll certainly visit, but because these tend to be good indicators of the hip part of town. 😛 Then, when I pull up the Airbnb (or VRBO) map, I know where I want to be.

How do you find good short-term rental deals?

To find good deals, there are only really three tips that come to mind.

Take advantage of your flexibility by doing a flexible search.
Both Airbnb and VRBO give you the option to search for flexible dates. For example, I’m interested in spending some time in the New River Gorge area this fall, but I don’t care exactly when I go or exactly how long I’ll stay. So I can select my rough duration goal (one week in my case) and my rough range of interest (September and October in my case).
As you can see in the results, I get to see all my options regardless of date range with an option for Sep 7-12 right alongside an option for Sep 20-25. This helps me avoid needing to go into each perspective property and try to examine their calendar of availability to determine the rates for one weekend over another.
Don’t be afraid to ask for a discount, especially if you have positive reviews.
Hosts are often willing to give discounts for mid-term and long-term stays, even if they haven’t pre-programmed extended stay discounts into their pricing automatically. If they’re not already offering an extended stay discount, you can simply ask if they would consider it. If they are already offering it, you can just ask for a discount for no reason at all, but offer a little bit of information about yourself to convince them what an easy guest you’ll be. I don’t usually suggest a discount amount; I simply ask if they would consider giving one. My success rate has been around 50% for this (with longer stays being more likely to work), so there’s really no reason not to ask.
Don’t be afraid to book longer than you actually want to stay, as some people don’t add discounts in until you reach closer to a month.
Some places heavily discount longer stays, so you may actually find that your options for a full month aren’t all that much more expensive than a whole week (or that a whole week is not much more expensive than 3 days, etc etc). In my sample search, for example, the high end of my week-long search results was similar to the low end of the month-long results. If you’re flexible on your duration anyway, don’t forget that a longer duration may actually be a better deal than a shorter one.