The idea of a globe-trotting existence sounds wonderful.
Nevertheless, plenty of barriers remain.
Some are practical.
The legal, payroll and tax ramifications of working from different locations in the course of a year are an administrative headache (Mr Chesky admits as much, and says that he will open-source Airbnb's solution to this problem).
Mundane issues like IT support become more complicated when you are abroad.
Working from anywhere is only feasible if your equipment functions reliably.
If the Wi-Fi at your Airbnb reminds you of what life was like with modems, your options may be limited.
If you spill suntan lotion on your laptop, the people on the hotel's reception desk are more likely to offer you sympathy than a replacement computer.
Another set of obstacles is more personal.
The carefree promise of working from anywhere is far easier to realise if you don't have actual cares.
Children of a certain age need to go to school; partners may not be able to work remotely and have careers of their own to manage.
The option to work from anywhere will be most attractive to people who have well-paid jobs and fewer obligations: childless tech workers, say.
For many other people, the "anywhere" in working from anywhere will still boil down to a simple choice between their home and their office.
That might be a recipe for resentment within teams.
Imagine dialling into a Zoom call covered in baby drool, and hearing Greg from product wax lyrical about how amazing Chamonix is at this time of year.
Resentment may even run the other way.
Hybrid work has already smudged the boundary between professional and personal lives.
Making everywhere a place of work smears them further.
Countries that used to be places to get away from it all will become places to bring it all with you.
Turning down meetings when you are on a proper vacation is wholly reasonable; it is not an option when you are plorking on a jobliday.
Antigua and Barbuda's tourism slogan, "The beach is just the beginning", sounds a lot more idyllic if the punchline in your head isn't, "There's also the weekly sales review".
Adding to the menu of working options for sought-after employees makes sense.
Mr Chesky's new policies will probably help him attract better people to Airbnb.
They are certainly aligned with the service he is selling.
But for the foreseeable future, working from anywhere will be a perk for a lucky few rather than a blueprint for things to come.