In an interview with News24, political analyst Benji Ndolo said that the east African country was facing many challenges that were not conducive for an election rerun.
Ndolo cited the lack of transparency within the country's electoral body as one of the reasons why elections were unlikely.
He said ballot papers also were not ready yet, and the fact that they were being printed elsewhere was aggravating the problem.
"With just 14 days to go to the election,there are too many challenges that are still unresolved. The ballot papers have not even been printed yet, and the company that is tasked with the printing of the ballot papers is based in Dubai. So, it's unlikely for a free and fair election to be held in such a short period of time,"said Ndolo.
The October 26 vote at first was limited to President Uhuru Kenyatta and opposition leader Raila Odinga, whose legal challenge of the August vote led the Supreme Court to annulit over "irregularities".
Odinga withdrew his candidature on Tuesday, citing a lack of election commission reforms.
Odinga's withdrawal threw East Africa's largest economy into confusion as Kenyans wondered how the new vote would go ahead.
But, the electoral body has said that it has not yet received his formal withdrawal, resulting in more political uncertainty in the country.
Subsequent to Odinga's withdrawal, the high courtapproved the participation of another presidential candidate who had received less than one percent of the vote.
This reportedly paved the way for the electoral body to allow all the presidential hopefuls to participate in the fresh vote.
"There is a lot of twist and turns for the country. The legal paralysis and string of demonstrations have put the country into political uncertainty. We are also expecting a lot more court challenges, and even more demonstrations. So, it will be difficult for a free and fair vote to take place," added Ndolo.
He added that there was also a possibility that Kenya could be split into two if the authorities continued with their political rhetoric.
Ndolo added that there was also a high chance of electoral violence as they were protests almost daily.
"We are likely going to see the country splitting into two if the leaders are not careful. In fact they are already people who are calling for a referendum. There is a chain reaction that would inevitably lead to violence. The ground for violence is even much higher than in 2007," said Ndolo.