Yes and No Paid Airbnb cannot be used for HDB flats. Private properties are another matter Free Couchsurfing may or may not be used for HDB flats not widely publicized There are legal implications for the owner of the HDB flat/local property The owner has to verify the legal documents of the renter and notify HDB. The rent if any paid to the owner is subjected to tax laws subjected to the length of stay which the renter should check themselves There are legal implications for the renter of the HDB flat The renter requires the necessary confirmation from the owner to their employment body for business activity, which results in gainful employment is subjected to local taxation, be it in director fees or employment income. The renter needs to update their address details with the local authority to not breach the local legislation else risk the loss of their employment passes Illegal overstay by the renter might result in the individual being imprisoned or exported where the individual can no longer use Singapore as an intermediary location for their personal or business purposes.