I've had many a conversation with clients who are nervous about driving in Crete. It can be a bit mad, but if you follow a few tips you will be fine.
You can have a beach holiday at the Villa, but we like to hire a car to get out and explore more of what's on offer. I would say also that the condition of the main roads is fab, though can be a bit rural in the villages.
1) Drive on the right hand side - the roundabouts take getting used to but they have arrows to guide you.
2) Drive very far on the right hand side on the main roads, as near to the emergency lane, there are some very hairy over-taking moments, so stay out of the way, not witnessed any crashes yet to be fair though!
3) Don't panic if you see a road sign in Greek, on the main roads it will be followed by the same sign in English.
4) Be aware that the Greeks don't much care too much about consistancy in spelling places, there is often a variation - Almyrida and Almirida are in fact the same place.
5) When driving through towns and villages, be wary that the vehicle/person in front may just stop for a chat with someone. They will also be oblivious to your car horn - you are on Cretan time now.
6) There are speed limits, and take care, as above, you are on Cretan time and the police won't understand why you'd be in a rush :)
7) Whilst driving in the beautiful mountains, beware that you may suddenly come across a shepherd and his flock of sheep. I like to think we are on their land, so let them get along to where they are, again hurrying them up is not going to help in any way.
8) On windy roads the Cretans also like to travel in the middle of the road, no idea why but take care.
9) Parking to Cretans can sometimes resemble abandoning of cars, but in the Cities, Chania etc. take care as there are parking restrictions and parking fines can be expensive. (Don't start me on whether they locals pay said fines)! If going into Chania the main road in has lots of free parking and not too far to walk in. The main supermarket in Chania also has very reasonable parking underneath.
10) Be careful choosing a car hire company. One of my clients was asked to leave 1000 Euro deposit with the company, at the airport, which basically wiped out all of his holiday cash. So be very specific about what is expected of you.
I have used 2 companies, namely Flisvos and Autoclub. You can look at their websites, but worth emailing them too to negotiate.
Nikki at Flisvos is English, and they understand English perfectly at Autoclub too. Both will deliver to, and collect cars from the airports, and the have regional offices in Western Crete if you have a problem - I never have.
This is an unsponsored post by the way, just being honest about good service.
If you have any further questions, do not hesitate to contact me :)