Analysis of the listing figures shows that around one in ten of these expensive properties are listed at rents in excess of $5000 per week. This includes the most expensive rental in the city: the $12,500 per week Vaucluse residence, available for a six-month lease.
This comes as the ongoing housing shortage and landlords' mounting mortgage bills force up prices in what is being described as the worst rental crisis in a generation.
This makes for some eye-watering rental figures that would have been unbelievable a year ago, when market conditions were not as tight and Australia had just reopened its borders to migrants.
The most expensive rental in Sydney totals $325,000 for a full six-month lease, which would balloon to $650,000 if extended to a full year. the security deposit for a luxury rental in Vaucluse is $50,000.
The most expensive rental on the Upper North Shore is touted as a good option for parents with daughters attending Pymble Girls' College, with long-term leases costing $10,000 per week or $520,000 per year.
Housing experts say the sky-high rents reflect a general housing shortage, rampant tenant demand and collapsing building approvals, which are forcing rents up across the board.
Demand is also rising for high-end rentals, often from affluent families who need accommodation while their existing homes are being demolished to make way for new construction.
Rents in Sydney have generally risen over the past year, and with it, expensive housing stock.
According to SQM Research, the average rent for a Sydney home is now at a record high of A$758 per week, about 25 per cent higher than a year ago (or A$153 per week).
"We're seeing pretty strong rents everywhere," said PropTrack analyst Angus Moore.
"It's not just isolated pockets of growth, which is what we saw a few years ago or during the (Covid) pandemic. Now it's a rise across the region and across the board."
"The question is, how long will it last? Given how tight the rental market is and with no signs of abating, it will probably continue through most of the year."
Real Estate Association of NSW chief executive Tim McKibbin said the high rental prices suggested there were not enough properties available for allocation.
"The queues for open housing are getting longer and longer," he said.
"We have to increase the supply of properties available to tenants, but we haven't heard from any political leaders what they will do about the lack of supply."
At the beginning of March, there were just over 9,300 properties available for rent, down from around 15,100 this time last year.
A search of rentals on the realestate.com.au website showed about 580 advertised at $400 a week or less, with 200 of them below $300 a week.
Those landlords who have converted their upmarket properties into holiday homes are even getting bigger rents, with a home in Point Piper currently available for short term rental at just $38,500 per week.