CSS Floating Divs with Different Height Are Aligned with Space Between Them

Floating divs, equal height - fill space with additional div without overflow

Pure CSS solution

Here is a DEMO of that solution.

In this DEMO, you see multipple Rows,
each Row can have a variable number of columns without stating anything in the markup, and without fixing any width. (the width is always divided evenly between the columns).
Each column is called ElementsHolder, and can have any number of Elements you want.

all the column in a row will always have the same height, and the last arrow in the row will fill that space.

In the DEMO you can see 3 Rows.
The First Row has the starting point, so no stretch needed there.
The Second Row has 3 ElementsHolder, without stating anything special in the markup, 2 of them will stretch to fill the gap.
The Third Row has 2 ElementsHolder, behave as expected.

notice that the stretching works regardless of the Elements height. (some of them have 2 or 3 lines of text, and it works perfectly)

If you want to use that technique, you only have to implement the other kind of boxes and arrows (Curve etc..)

The solution is done by using the new CSS flex model.
the direction is set via flex-direction: row;,
Each row has ElementsHolders that gets equal width.

each one of those ElementsHolder is also a flex box, but this time his direction is opposite (flex-direction: column;).

the child's of ElementsHolder are Elements & Arrows, I dont want them to have equal height, but to span excatly the natural height. except the last arrow, that should span the rest of the container.

all of that is achieved using the flex property with the appropriate values.

More about the flex-model can be found HERE

How do I keep two side-by-side div elements the same height?

Flexbox

With flexbox it's a single declaration:

.row {
  display: flex; /* equal height of the children */
}

.col {
  flex: 1; /* additionally, equal width */
  
  padding: 1em;
  border: solid;
}

<div class="row">
  <div class="col">Lorem ipsum dolor sit amet, consectetur adipisicing elit.</div>
  <div class="col">Lorem ipsum dolor sit amet, consectetur adipisicing elit. Ad omnis quae expedita ipsum nobis praesentium velit animi minus amet perspiciatis laboriosam similique debitis iste ratione nemo ea at corporis aliquam.</div>
</div>

different height divs float in two columns

You're going to have to do this with JavaScript. If you're using jQuery, there is an excellent plugin called Masonry. There is also the non jQuery version.

To quote the README on GitHub:

Masonry is a dynamic grid layout script. Think of it as the flip-side
of CSS floats. Whereas floating arranges elements horizontally then
vertically, Masonry arranges elements vertically, positioning each
element in the next open spot in the grid. The result minimizes
vertical gaps between elements of varying height, just like a mason
fitting stones in a wall.

The single column layout is probably what you're looking for.

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If you don't mind leaving older browsers in the dust, there are the CSS3 column properties. There's an example here, on Quirksmode, and some documentation on the MDN.

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