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I was wondering what the actual size was of a Tiny creature. Could they fit under doors, through keyholes, or is that too small?
For example: could I use an imp familiar to scout an area, by making it go through a crack in the window, or maybe through a keyhole?
Is the short answer. Long answer is below:
PHB page 191 lists the the size categories, in terms of area controlled in combat, given in feet:
Tiny - 2 1/2 by 2 1/2 ft
Small - 5 by 5 ft.
Medium - 5 by 5 ft.
Large - 10 by 10 ft.
Huge - 15 by 15 ft.
Gargantuan - 20 by 20 ft. or larger
With that in mind, it's unlikely that a tiny familiar could slip under doors or through cracks in window frames.
Specifically, many Medium creatures stand between about 4' and 6' tall. As Medium, they control 5' of space around them.
It seems safe to assume that this is pretty closely related to 'wingspan', which is usually about equal to the height of a humanoid. That is to say, the widest you can stretch your arms is about equivalent to your height.
2.5' wide is 30", or about 75cm for our metric friends. That's a pretty decent idea of how tall our tiny man stands. This will define the high end of the scale -- we may have smaller creatures that will fall significantly below this.
Based off of this image from NASA, we can get a rough idea of human proportions. Unfortunately this only uses generic 'units', but it's enough to go off of.
The main thing to note is that the ratio of height to chest depth is 805:236. Applying this to our 30" height, we get something around 9".
Honestly, however, the ratio in the image seems off. Measuring in GIMP gives something more like 162:29. Using that as our ratio gives us something more like 5.4", which seems closer.
Additionally, we can run a similar ratio to try and determine how broad-shouldered our tiny man is. Unfortunately, they change around units here -- we can't directly correlate height to broadness.
What we can do is estimate the length of the torso, based on height; then compare the torso height to the broadness.
Let's say that the torso length is about 1/3 the height of the humanoid, so about 10". At a ratio of 612:378 torso:breadth, we get a rough, but workable, 6".
In short, This means we can visualize our tiny man as a box, about 30" x 6" x 6", although it's technically more of a diamond shape. There are some limitations to this model - imps aren't tiny men, and some measurements may vary.
These measurements are rough -- a tiny creature could contort or deform itself (much like spelunkers) to get through narrower gaps than this would suggest. We may also be off by an inch here or there.
Even more significant -- these are based off the measurements of a tiny man.
Imps likely aren't tiny men.
They will have different measurements.
However, these give us a good idea of what order of magnitude we're working with -- the imp may vary by something like 25% in any of these measurements.
We're not deforming these too much. It seems clear that we're not squashing a tiny humanoid that's 30" tall through a 2" crack.
J.A. did mention that sprites are about 8" tall - this gives us new numbers. Let's round that to a friendly 10" tall because it it works nicely with numbers and keeps us from doing unnecessary math.
We can just divide the measurements from above by 3, giving us something like 10" x 2" x 2".
For creatures under a foot in size, it's plausible that they could slip beneath the gaps in rougher-hewn doorways.
Still probably not the windows, though.
I've always thought of Sprites are about 8" to 2' tall (I've seen similar numbers in homebrew Sprite PC Races) There is a diagram on page 248 of the DMG that shows the realative size. You can clearly see a winged tiny creature (sprite or pixie) as being 2 feet tall from the tip of the toe to the tip of the wing. From the 3/4 view, looking to be between 6 inches and 1 foot wide, wings included. I'd think that is much to tall to fit through a crack in the window or lock upright. But you might be able to argue that head first they might be able to squeeze through -- we'll get to that.
Imps I've always thought of being between a parakeet and a cat in size. I don't know if I ever saw any reference to an actual height. I'd be hesitant to think it'd be able to fit.... but it does have shapechanger ability and could make itself a spider small enough to fit.
RAW, you can squeeze through the size of the next smaller creature at double the cost of the movement. There is nothing smaller than tiny, so what that means for them is up to the DM. Talk to them about what size they see these creatures being.
If you have an Imp familiar, you're either a warlock, using the variant rules, or a homebrew. If you are a warlock, one of the spells on your spell list is Gaseous Form, and it is a spell with a range of touch. You could cast it through your familiar on your familiar. Granted that takes two valuable resources -- a spell slot and concentration. But it is an option if the DM says the Imp doesn't fit.
As the other answers make clear, "Tiny" in fact covers a very large range of sizes, since it's the smallest one stated and yet must include everything from a cat to a spider.
It's weird that the Monster Manual doesn't give more info on the fantasy creatures. We already know how big a cat is, and that spiders vary widely, but calling an Imp just "tiny" leaves a LOT to the imagination.
This Forgotten Realms Wiki Entry has a lot of extra info about Imps. I don't know if it's all "true" for 5e or not, but according to the 3.5 monster manual Imps are:
approximately 2 ft (0.61 m) tall humanoids that weighed about 8 lb (3.6 kg)
That makes sense to me and answered my question. The wiki article has a lot of other flavor that would probably help a Warlock with RP stuff too.
Coming back to the question, as others have said you are lucky and it can just morph from an invisible Imp into an invisible spider and go on through. Since they don't tell us what size of spider it is, personally I'm going to say it's a tiny-ass spider because it makes the Imp familiar an even more OP spy ;)
This is a tricky question because Tiny is a very broad category.
In a previous version of D&D, they had an even smaller size category called Diminutive. The example creature for Tiny was a Cat. The example creature for Diminutive was a sprite or a bug.
5e got rid of Diminutive, and now Cats and Toddlers share the same size category as spiders. (I know D&D has spiders much larger than a person, but I think it's safe to assume the type of Spider listed as a Familiar option would be a common house spider).
So, it's kind of up to yours and your DM's best judgement how big a Tiny creature really is. I don't think your Imp is small enough to slip through a keyhole or a crack in a window, but if it shape-changes into a spider, I'd say it could do those things easily.
