Mohammed Isaq, 62, and two children Sultan Khan, 28, and Amani Khan, 27, ran the businesses which 'misled' members of the public, promising 'safe and secure' parking while they flew off.
However, after handing over the keys to the company, many were lost, stolen or found damaged in a muddy field upon their return, Manchester Crown Court heard.
In one case, a man returned from his holiday to find his car had done an extra 688 miles on the clock.
Another car was discovered to have cannabis and Rizla papers. Other cars had damage to the alloys, windscreen and body work.
Isaq was jailed for 17 months, while his son and daughter were handed a community order.
Outlining the facts of the case, Adam Pearson said the firm operated out of their family home at Davenport Green Hall in Hale Barns, and also used local fields and residential streets.
The companies advertised on their own website and on price comparison sites that cars would be left in a secure car park, covered with CCTV, flood lights and 24 hour staffing.
"Those advertisements did not accord with the reality of the situation," Mr Pearson said.
The parking business was first carried out by 'Eat, Meet and Greet Ltd' in which Sultan Khan was the sole director. It later dissolved in March 2017
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