Do these names fit well with eachother?

[Donnaj28]

June, Lilia, Claire, Milo & Oliver

I think they're nice together. Only comment would be that there are lots of Ls.

Would you recommend the name June with the L names or April

Apart from multiple L's; they are all quite different in style. Oliver is a classic name that is currently very popular and Claire is a classic that's currently a bit dated. June is fairly old-fashioned, Lilia has never been popular, but Milo is quite trendy at the moment.

Jane, Lily, Clara, Miles and Oliver would be a more classic sounding sibset - more difficult to guess what time period they were born in.

They’re all fine. I think Oliver feels a bit more popular than the others.