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I am so glad this question exists on Quora. I hope to clear up the mass confusion. Upfront; I have been operating Sharing Economy businesses in Asia since 2012, which is why I have looked into the matter deeper than most.

In 2012, I consulted with a reputable law firm (name withheld) that has issued me a written response about the URAs statements on short-term leasing. Here are their findings paraphrased:

"...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 (Leasing guideline) 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”

Their advise goes on to say that participants of short-term leasing should inform their guests not to disturb neighbours or the URA has the right to step in according to the letter of the law.

To summarise their response in points:

  • 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 if guest causes disturbance to the neighbourhood.

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This doesn't mean that everyone can operate a short-term rental. The HDB rules are very clear about disallowing subletting; So 80% of my countrymen are unfortunately powerless to defray the effects of inflation through maximising the yield on their most valuable but illiquid asset.

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The above are facts. Now here are the mosaic of opinions on the matter after speaking to a few hundred guests, owners, regulators, companies, students, schools, medical tourists and hotel owners personally;

  • Landlords of investment properties (non-owner occupied) are for it; mainly due to pressure to service mortgage.
  • About half of landlords of owner-occupied properties are for it due to supplementary income; background is usually recent unemployment driving the activity to host
  • The other half against it mainly due to discomfort of unfamiliar faces
  • Guests want it
  • Neighbours will activate the regulor when drunks or prostitution is involved
  • Hotel associations hate it
  • Regulators usually neutral until hotel associations put pressure
  • Most common reasons cited by regulator are: Tax and Disturbance
  • Real demand is driven by expensive hotels and few viable options for the person who staying for 30–180 days
  • Solution to social problem faced by retiree in asset rich cash poor position
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