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David, I'm not an expert but like Lydia my understanding is that your friend will be liable for the additional 3% SDLT if he decides to keep the holiday flats that he currently owns. But, if his girlfriend does not currently own a property, she might possibly be able to buy the new property in her own name without incurring the additional 3% duty (depending on the exact nature of the 'boyfriend-girlfriend' relationship).. This option would not of course be available to them if they were foolish enough to get married.

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