May 13, 2026 3:48 pm EDT

Jack Grealish cut a glum figure as he arrived back in rainy London on Wednesday, after a sun-soaked family holiday in Barbados. 

Joined by his girlfriend Sasha Attwood and their daughter Mila, 19 months, the footballer pushed a trolley full of suitcases through the arrivals terminal in Heathrow Airport. 

Jack cut a casual figure in a grey hoodie and shorts after the long-haul flight, with model Sasha, 30, opting for a grey co-ord.  

The family stayed at the luxurious Sandy Lane Hotel during their week-long stay, where prices at the five-star resort start at £1,000 per night. 

Jack, who suffered a season-ending foot injury during Everton’s clash against Aston Villa in January, appeared to be doing well following an operation on a stress fracture on his foot in February.  

The forward had a 10-week check up call with the surgeon and was told it ‘could not be looking any better at this stage’.

Jack Grealish cut a glum figure as he arrived back in rainy London after a sun-soaked family holiday in Barbados

Joined by his girlfriend Sasha Attwood and their daughter Mila, 19 months, the footballer pushed a trolley full of suitcases through the arrival terminal in Heathrow Airport

Sasha took to Instagram to share an insight into their family holiday. 

In one photo, the model and Jack beamed as they posed with their daughter. 

Sasha and Jack welcomed Mila in September 2024.

When their daughter arrived, Jack called it ‘the most special moment of my life’.

However, he also reflected on the year as one of the hardest of his life after he sat on the bench for his then team, Manchester City for multiple games.

He said: ‘Last year, the whole year itself, it was weird because my little daughter was born, but apart from that it was one of the most difficult years – probably the most difficult year of my life for many reasons, on and off the pitch.

‘I found it really difficult. But it’s a new year, a sort of fresh start, and hopefully I can kick on from here.’

Daily Mail Sport recently revealed how Everton are growing in confidence that the footballer will be back with the club next season. 

Sasha took to Instagram to share an insight into their family holiday. In one photo, the model and Jack beamed as they posed with their daughter

Jack cut a casual figure in a grey hoodie and shorts after the long-haul flight, with model Sasha, 30, also opting for a grey co-ord

The family stayed at the luxurious Sandy Lane Hotel during their week-long stay, where prices at the five star resort start at £1,000 per night

Jack, who suffered a season-ending foot injury during Everton’s clash against Aston Villa in January, appeared to be doing well following an operation on a stress fracture on his foot

Jack was busy on his phone after landing 

Daily Mail Sport recently revealed how Everton are growing in confidence that Grealish will be back with the club next season

Officials at Hill Dickinson Stadium are keen to retain the services of the on-loan Manchester City playmaker, who has a year remaining on his contract at the Etihad Stadium.

Grealish had been a revelation following his loan move, until injury cruelly ended his season in January.

He has remained on Merseyside for a long period of rehabilitation after suffering a stress fracture to his foot – something those at the club believe to be a hugely positive sign.

The midfielder’s £300,000-a-week wages could prove to be a stumbling block, although Everton managed to shell out around £12m to borrow him for a year and the club’s financial position has improved significantly since their move to their impressive new stadium.

An option to buy at £50m is thought to feature in the agreement, although Toffees bosses may well feel something in the region of £20m would be more in keeping for a player with 12 months left on their deal.

Manager David Moyes is thought to be keen to keep the attacking midfielder, who proved to be an instant hit with supporters.

In his time in a blue shirt, he scored twice and provided six assists in 22 appearances and was a key part of what has so far been a much improved season which could end in European qualification.

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