Brit joiner Ryan Hoyle, 38, took seven of his friends to the Five Jumeirah Village Hotel, splashing out on two top-floor penthouses for £10,000 each.
The builder from Rochdale, Greater Manchester, had previously only been abroad twice in his life for two stag dos in the Spanish resorts of Magaluf and Benidorm.
Ryan scooped the huge prize back in April last year, but due to Covid restrictions, he has so far been unable to celebrate properly with his mates.
After his win during the first Covid lockdown, Ryan's celebrations were limited to a socially-distanced beer in the garden with his brothers.
But he and some of his oldest friends enjoyed first-class flights, luxury five-star accommodation and £1,700 bottles of champagne on tap over the new year.
They also partied at the Zero Gravity beach bar and club, where pop star Justin Bieber recently hosted a party.
Ryan told The Sun: "Covid's made things tough for everyone so it was great to be able to get away and have a party.
"I've known all the lads for around 20 years and wanted to treat them to a trip they'd never forget."
One member of the party, Peter Garry, who has known Ryan for decades, said: "He's the best friend anyone could have.
"There's never been anything flash about him and the win hasn't changed him a bit - he's still the same great guy."
Joking how the pair had only ever disagreed on football - Peter supports Burnley while Ryan is a Man Utd fan - he went on: "We never in our wildest dreams expected him to be so generous and have all had literally the best week of our lives."
At the club, the group downed champagne and fancy Ciroc vodka worth £1,700 a bottle while a gaggle of beauties surrounded them.
Single dad-of-one Ryan plans to take his 11-year-old daughter on a trip to Disneyland, Florida once Covid restrictions ease.
After flying out on economy on Emirates as they were the only seats available, the party were treated to a first-class return costing £6,000 each.
Peter added: "It was the perfect end to the perfect week."
Shortly after his £58,366,487 win, a source close to Ryan told the Daily Star he had been bombarded with offers of sex from mystery women.
He also received notes through his door from strangers asking for help.
The source said: "Ryan knew the letters asking for cash would start arriving pretty soon after news of his win broke.
"He's a little more surprised at the offers of relationships from women and some are pretty graphic.
"But he's a level-headed guy and he's not going to have his head turned by 'Sandra from Swindon'."