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Consider the following scenario in the UK?
Is this a taxi service? Do I need a commercial/taxi licence?
It depends somewhat on which city you're talking about, but this sounds very similar to the business model of Uber. It almost sounds like you're considering becoming an Uber driver, with the exception that you're making trip destinations match their origin. Uber is active in cities like London, Birmingham, Bristol, Manchester, Glasgow, etc. and has a sizeable base of both riders and drivers, indicating a regulatory environment that is favorable or at least not sufficiently hostile to such a model.
London has regulations restricting use of taximeters, but last fall the high court ruled that Uber's app does not constitute a taximeter that would violate the regulations. The mayor said this was the primary issue around the legality of the service there, and this is the main regulatory dispute in Wikipedia's list (which may not be all inclusive). January headlines from this year heralded the lack of regulatory obstacles to Uber's operations in that city.
You should probably first check with your insurance company, especially if there are FAQs on their website or details in your insurance policy, because you might not be covered under that policy on those drives without some additional premium.
Check out the UK's Licence Finder to help find out what licences you might need for business activities. Also check out the government's official page on "Driving licences for taxis and private hire vehicles" for information on Private Hire Vehicle (PHV) licenses.
As an aside, a perspective on how times have changed:
1998:
2016:
First, it makes you a business because you take money. There are some very low limits where HMRC (the UK inland revenue) doesn't care much, but above that you must either start a limited company, or fill out a tax self assessment where you declare the money as income from being self employed. If you don't tell them, that's tax evasion.
If you transport people for money, then you need a license that allows you to transport people for money, and you need a car insurance that insures you when you transport people for money. If you don't have that insurance, and there is an accident, then the insurance company will tell you that your normal license is void, you won't get a penny, victims won't get a penny, victims will sue you, and this may be one of the situations where having a limited liability company doesn't protect you.
