Noted also for its jokes and visual puns, A holiday at Mentone has been described as "a witty comment on the transformation of nature into artifice through fashion, decorum, and painting".

Conder had met the Melbourne-based painter Tom Roberts in Sydney the previous year and again at Easter 1888, where the pair had painted en plein air together at Coogee Beach.

In Melbourne, Conder initially based himself at Roberts' Grosvenor Chambers studio and A Holiday at Mentone was his first painting in the new city, completed within a few weeks of arriving there.

[2] During the summer of 1886–87 at Mentone, Roberts and Frederick McCubbin established an "artists' camp" and, as legend has it, encountered for the first time the young Arthur Streeton, painting en plein air on the beach.

[3] Roberts' 1885 painting Winter morning after rain, Gardiner's Creek, with its high horizon line and bisecting bridge, may have also been a reference point.

[5] In the background, an elderly couple dressed conservatively in black observe the three young beachgoers—progressive members of Melbourne's rising middle class.