A New Zealand family of four who turned up at Caribbean at Keppel Bay expecting to pick up apartment keys for a four-night stay booked on Airbnb were devastated when they were told such short-term rents were outlawed.
The case highlights problems with allowing rental listings for illegal stays as consumers may be none the wiser.
In this instance, the Haynes family were left sitting by the condominium's pool for an hour with their luggage last Friday before a security guard told them the bad news.
"We were taken aback as we were not aware of this rule," said Mr Blair Haynes, 43, who was with his wife, Michelle, 39, and sons Baxter, seven, and Flynn, five.
Private homes here are subject to a minimum rental period of three consecutive months, and six months for public housing.
Mr Haynes, a commercial property developer, paid about $1,500 to book the two-bedroom unit for four nights.
When he and Michelle confirmed that the rental was illegal later that morning, they checked into the Regent Hotel instead for about $500 a night. "It was a hassle to move again after the long flight. The kids were also taking it poorly and afraid of the guards in their uniforms," Mr Haynes said.
"Airbnb should not have put us in this situation in the first place, knowing full well that it is illegal. They should be held liable for what they are doing, which is not right."
It seemed the host, who goes by the name Xiao Han on Airbnb, was aware of the illegal rental.
A message she sent to the family last Friday, after Mr Haynes messaged her about being turned away from the condominium, read: "In Singapore, the Government don't allow our rent the unit to the tourist (sic), but can give it to our friends and relative to live... Kindly tell them that you live in the friend's home instead."
After seeing this, Mr Haynes decided he "didn't want anything more to do with the host", and contacted Airbnb, which gave him a full refund.
When The Straits Times contacted the host, who used a mainland-China-registered mobile phone number, a Ms Xiao Han answered and spoke in Mandarin.
But when Mr Haynes' case was brought up, she would not comment. Subsequent attempts to contact her were unsuccessful.
The listing was removed and unavailable yesterday.
Airbnb said its instructions to hosts are clear. "We proactively encourage all hosts to consult local laws and regulations before listing their property on Airbnb," said its head of public policy for South-east Asia, Ms Mich Goh.
On the Haynes family's case, Ms Goh said: "This is further evidence of the need for a regulatory framework that reflects how people increasingly want to travel.
"We are optimistic that our community of hosts and guests will get the clarification it needs within the next two weeks when the Government publicly shares its proposed short-term rental rules and begins its public consultation on the matter."
The Urban Redevelopment Authority (URA) investigated about 820 cases of unauthorised short-term accommodation in private residential properties last year and a further 130 in January and February this year.
Two Airbnb hosts were prosecuted last month for violating rules on short-term rentals.
National Development Minister Lawrence Wong told Parliament last month that while "URA will continue with its current enforcement approach on errant home owners", action will not be taken against listings, as "advertising on home-sharing or rental websites... in itself is not an offence and it is not regulated under the Planning Act, because these listings typically do not indicate the tenure of lease".
Still, when contacted about the cases like the NZ family's, a URA spokesman said: "Advertisements, including listings on home-sharing platforms, can provide an indication that certain private properties are potentially being misused.
"These leads can be used by URA as part of investigations and eventual enforcement action when the infringement has been ascertained."
She added that a public consultation will be conducted soon on a regulatory framework for using private homes as short-term rentals.