Meet the Frigidaire Cool Connect Smart Window Air Conditioner: a smart 8,000-BTU cooler with WiFi that can be controlled using a smart device. In fact, you can turn the unit on/off, change its modes, and control fan speed. It cools up to a 350 square foot room.
The cooler is compatible with iOS and Android devices, so you can put it on a schedule conveniently. You also get notifications when you need to change filter or perform maintenance. Costs under $300 at this time.