Hi Ebony,
The big difference in pricing is largely down to how much the different insurers want your business. When you ask for a travel insurance quote you must advise them about your diabetes. At that point they will do one of 3 things:
1) Offer you insurance that covers you fully, including any medical problems that might arise from your diabetes
2) Offer you insurance that covers everything EXCEPT your diabetes (i.e. not covering any pre-existing condition)
3) Say they are not prepared to insure you.
Most travel insurers do the second of these, but unfortunately they "forget" to mention to you that the policy they are offering excludes pre-existing medical conditions. You only find out when you read the small print after you have paid them. So when you get a quote always ask, before you agree to anything, whether pre-existing conditions are fully covered.
If you find it difficult to get insurance, there are several specialist insurers that insure for diabetes, but sometimes they offer only annual policies and I guess that you would want a single trip one? Someone recently said they got a good quote from M&S for travel insurance, so they might be worth a try - but be sure you ask whether the policy covers your diabetes (for example if you had a diabetes-related emergency that meant you had to cancel the holiday, or were taken ill while away on holiday).
Edited by Dennis
Just checked M&S policy conditions online and they say their policy does not cover pre-existing medical conditions. You need to ask them for a special quote and they will quote you a price if they decide they are willing to cover you.