The affordable Meross outdoor smart plug includes two smart plugs, each operating independently of each other. This advantage means that you get two sockets added to the Home application, so you can assign one to the holiday lights and another to an inflatable in the yard. Dust and weather resistance IP44, plus a fireproof housing, keeps it safe all year round.
$ 26 on Amazon
If you need outdoor power in a confined space, then you need iHome ISP100 Outdoor Smart Plug. This outdoor plug is the thinnest around, measuring just under 2 inches wide with a 6-inch power cord. The iHome plug provides a lot of power with a single smart socket capable of handling up to 1,800 watts.
$ 65 on Amazon
Belkin's smart outdoor Wemo Wi-Fi connector packs two sockets connected together into one simple control. In addition to HomeKit, this plug works with Wemo, Alexa Amazon and the Google Assistant. Through the Wemo app, you can set the exterior lights to turn on randomly every day, in case someone throws you the place.