Thanks ladies, thought I would give an update.

After a night of Olive waking 5 times I decided to embark on a new journey. I went to the library and got out 'No Cry Sleep Solution For Toddlers and Preschoolers'. I then changed our bedtime routine, spending time in Olive's room playing away from tv etc before bed. I put a chair beside her cot. We made a fuss at 7pm of saying good night to Daddy, chose two books, made milk and went into the room. I sat on the chair with Olive on my lap for milk and stories. As she loves teddies and has no other comfort thing I decided to make a teddy her sleep comfort. After the 2 stories it's lights out then a tuck in with teddy.
The first night I put her in the cot after stories she started to cry but I quickly started singing a lullaby and she stopped instantly and finished her milk. I rested my head agaist the rail of the cot without giving eye contact. I took about 35 mins of tossing and turning but no tears. When she was looking really tires I left the room and she went to sleep by herself!!!
I am now usually able to leave the room straight after the tuck in, occasionally having to return to sit beside the cot but Olive is self settling for over a week now. She is still waking 1-2 times but that is a whole lot better then 5 and hopefully we will get there eventually but I am just so happy that the no cry method has been so easy with just a few changes.
Thanks for your support everyone!