The 27-year-old beauty - who caught potentially-deadly malaria after a trip to Africa with her close pal and rumoured boyfriend in June - is spending time with the 'Dancing With The Stars' professional in Cape Town to mark the turning of a year which also saw her split from husband Ashley Cole amid allegations he had cheated on her with several women.
A source said: "He wanted to make sure Cheryl had a good start to 2011 after her worst year ever.
"Then he just told her to pack a bag as he'd organised a holiday for them."
Cheryl's friends have been concerned about her travelling back to Africa so soon after recovering from malaria - a disease spread my mosquitoes - but worries were settled when Derek confirmed the insects in the country do not carry it.
The source added to The Sun newspaper: "Friends warned about going back to Africa so soon afterwards. But Derek did his homework and found Cape Town to be a malaria-free region."
The pair are staying at a luxury £3,000-a-night villa where they will be able to enjoy a 24-hour butler and a personal chef.
The insider said: "Cheryl can relax and be pampered which is what she wanted."
Meanwhile, the 'Flood' singer is believed to be taking acting lessons in preparation for a possible judging role on the US version of UK TV talent show 'The X Factor'.
A pal said: "Alongside the acting lessons, she'll be getting a coach to train her for the judges' role In America."