Here’s a photo found in an old album of snapshots at Antique Alley. It shows the old Haleiwa Hotel, apparently in its prime.

The album also includes photos at the Waikiki Natatorium, which wasn’t completed until 1927.

But according to a history of the Haleiwa Hotel:

By the late-1920s, it was hard to maintain the luxury and level of service at the hotel. What had been built two decades before to lure passengers to ride the train no longer applied, as more and more people owned cars.

In 1930 the railroad closed the hotel and it became a private ‘Haleiwa Beach Club.’ Later, the Haleiwa Hotel became the ‘Haleiwa Army Officer’s Club.’

So I’m not sure when this photo was taken, but the general time period seems to be perhaps the late 1920s or early 1930s.

The old Haleiwa Hotel.