Yes. Most standard snowbird insurance plans will cover you for multiple trips. You can buy single-trip insurance if that option fits your travel plans better, but that type of coverage usually falls under general travel insurance rather than under snowbird insurance.
Snowbird insurance policies usually outline a maximum number of total days that you can be out of the country. Of course, always read the conditions of the policy carefully before you buy it. And remember to ask your insurance provider or broker for advice on the right product.