How long does it take for a facial hematoma to heal? Does it need to be drained if it hasn't gone down within 2 weeks? (Photos)

coco: If there is a liquid hematoma, it can be aspirated with a needle in the office, and this may help the bruising resolve more quickly.  The numbness is more likely related to nerve trauma from the fracture, not necessarily the hematoma.  See a plastic surgeon, they can assess whether or not the hematoma has liquefied...this usually takes about a week; at first it is clot and can't be sucked out.  Another reason to have it aspirated is to prevent infection...bacteria from your cheek sinus love blood as a growth medium and it theoretically could turn into an abscess, though this would be unlikely. 

Sorry about your injury.  Continue to have follow up with your surgeon. 

Some maxillary injuries may require surgery if you are experiencing visual, bite or nasal difficulties.  Many heal without the need for surgery. 
Soft tissue injuries may been laceration and or simple abrasion care using Aquaphor ointment.  
In your case your pictures show a great healing response. I would expect continual healing. In one to two years it may be difficult to see any sequela.

I'm glad you are alive.