Location: Barbados
Purchased: Visited frequently
Current Value: $35 million*

Simon Cowell is a huge fan of the sunny island Barbados and over the years he has visited it numerous times. The television personality is believed to always stay in a luxurious villa which is listed on the market for $25million, as of 2020. Apart from Cowell, the property has also been visited by Prince Harry and Meghan Markle, Elton John, Rihanna, and Nicole Kidman.

While the property doesn’t come with its island, it is located on a 1.3-acre estate in the St James district and it has ocean views.  The villa has 20,000 square feet, 10 bedrooms, a private gym, a spa and cinema room, and numerous other luxurious amenities most people could never afford. According to The Sun, Simon Cowell used the property as his Judges’ Houses base on the X Factor.