This turns out to be surprisingly nuanced. In short, while officially discouraged, short-term rentals are legal, or at least not illegal, in Singapore.
The Urban Redevelopment Authority (URA), the Singapore government body responsible for private housing, makes it quite clear that:
Private residential properties or their rooms within the premises
should not be rented out on a short-term basis for less than 6 months
on a daily/weekly/monthly basis.
And quite a few third-party sources go on to conflate this with the HDB's legal prohibition on sublets, with the URA also doing its best to blur the two. But a rather fascinating answer on Quora by James Chua, CEO of Singapore-based short-term rental company PandaBed.com, quotes his own laywers:
" ...the Guideline is not law as it is not codified in a statutory instrument. The URA, in response to a query from the public, made a statement in The Straits Times on 26 May 2012 in which it conceded that the Guideline was not a ‘ruling’, but stressed that the URA “issue[s] guidelines from time to time to provide transparency and clarity on how the URA exercises its functions under the Planning Act” ... "
And goes on to summarize:
- Short-term renting is NOT ILLEGAL for private property
- The popular "6-month minimum rental period" quoted widely in the press is not a law but a guideline by the URA (Leasing guideline)
- Owners of short-term rental homes should ensure guests don't cause disturbance to the neighbourhood or they are at risk of getting in
trouble with the URA
- The URA has the authority to take action only if guest causes disturbance to the neighbourhood.
Singapore being Singapore, the URA will probably at some point "scare the monkeys by killing a chicken" and make an example of some poor Airbnb host who rented his apartment to a bunch of frat boys who terrorized the neighbours... but at least for time being, it's OK to host, and it's OK to stay with a host. Yay!