Multi-generational travel is one of the most meaningful ways families spend time together — but it’s also one of the easiest ways for vacations to feel overwhelming if they aren’t planned thoughtfully. When grandparents, parents, adult children, and kids travel together, everyone brings different needs, energy levels, and expectations.

When it comes to planning a family getaway in the Florida Keys, the right vacation rental can make all the difference between “just okay” and “absolutely unforgettable.” Here are our top insider tips to help you get the most from your Florida Keys vacation rental—financially, emotionally, and experientially.