Simon Morgan, 43, had gone away with wife Claire Morgan and son James, 15, on a last minute break on 3 March, meaning James missed two days of school.
While they were there, Morgan received a message from Stanwell School in South Wales, that read: "James Morgan was absent from registration. Please can you text a reply with the reason for this absence."
Morgan replied with a picture of James stood in front of Dubai's hotel Burj Al'arab, much to the amusement of his son and all of his school friends.
"We only found out about the holiday the day before as it was through the travel agency that we run, so we genuinely didn't have time to plan," Morgan said.
"I know I should have told the school beforehand, but if you ask on things like this unfortunately they often say they don't approve of it, so I took a gamble.
"They didn't reply to the text so I think it paid off."
Morgan said his son is doing very well at school, is on target for excellent GCSE results and misses very few days.
"When I got the message I decided to send the picture because I think a picture tells a thousand words," he said.
"I think from the photo it was then quite apparent where he was.
"It was light-hearted banter, though admittedly it's not the first time I have done it. James obviously thought it was fantastic and all of his friends loved it too.
"My wife takes my humour in her stride – though she does say that one day it might bite me on the back side."
In previous text message replies to the school, Morgan's responses have apparently included blaming hippos for James being late in and not wanting James to "sh** his pants" in the classroom for why he remained off ill.
In May 2015, when the school enquired why James was absent, Morgan said he replied: "Oh dear God. We took James out last night to celebrate the end of his GCSE exams. We had a couple of cocktails.
"Not sure what happened next, but I've woken up in a hotel room with a six foot plastic flamingo in my bed and what looks like Mike Tyson's tiger in the corner of the room.
"I think we may be in Las Vegas? I've no idea where James is. Will check the roof."
James, who hopes to one day study design or architecture, claims his dad has developed a reputation among both his classmates and teachers alike.
"Everyone takes it in good humour," he said.
"One of the teachers even high fived me once when they heard about his latest prank.
"Most of his pranks go down well – apart from the one where he said he would keep me in a cardboard box outside school and feed me gruel. I don't think the staff saw the funny side of that one.
"But I think the picture of me in Dubai is the best one yet. It's very funny.
"As soon as he sent that one in, I knew he had done something as my phone started going crazy with friends telling me how word had got round at school.
"My dad is very funny. He's always making us all laugh. He's a very excitable and happy person so he's fun to be around.
"I look up to him a lot and we are very close. He's really supportive of me at school too."
Stanwell School declined to comment.