Steph,
it is an implicit page break issue. We've been checking if it is possible to implement a fix. (it is quite tricky: PD4ML prints floats after the main content, so a page break "signal" comes from a float too late - when a portion of a text, supposed to go to the next page, is already printed on the current one).
As a workaround I would recommend to add a conditional page break tag between <div>s:
...
</div>
</div>
<pd4ml:page.break ifSpaceBelowLessThan=300>
<div class="Entry" style="...">
<img class="Image"
...
where "300" more-less matches the image height.