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Most options are available in March/April, but that is also when everyone moves
If your contract ends in September, start looking around June. Then settle on something by July (at the latest). Give notice you’re not renewing 30 days before September (they may auto renew otherwise).
Golden Week to Summer (August) is off-season for moving, so you could keep the cost down. But then again the room availability will be down as well so your choice might be limited.
Just look around for new apartment every week or so. If you find a good place then bite the bullet there. You’ll be much happier.
If you are picky about stuff, I’d say starting looking as soon as you can. You’re current apartment likely has a two month notice of leave clause, so if you happen to find something early, you can often shift your move-in time to accommodate closely.
March/April will have the most available apartments, but chances are the fees (key money etc) will be higher that time of year. Plus, things move really fast.
My best advice is to be your own advocate. Try finding a few properties you are interested in before visiting a realty company. They will often try to upsell places to you that don’t fit your needs.
If you speak Japanese, [this app](https://apps.apple.com/jp/app/%E8%B3%83%E8%B2%B8%E7%89%A9%E4%BB%B6%E6%A4%9C%E7%B4%A2-%E3%83%8B%E3%83%95%E3%83%86%E3%82%A3%E4%B8%8D%E5%8B%95%E7%94%A3%E3%81%A7%E7%89%A9%E4%BB%B6%E6%8E%A2%E3%81%97-%E9%83%A8%E5%B1%8B%E6%8E%A2%E3%81%97/id717072560) is the best out there since it combines all the top property companies into a single search.
I was very picky about location, size, rent, pet-friendliness, and foreigner friendliness, and I ended up searching for half a year before I found the perfect location!