Got something specific in mind for the high season? Start your search at least six months in advance.
If you're going to Mardi Gras, Oktoberfest, or any event that draws crowds from around the world, secure your rental at least a full year ahead of time.
During the off-season at popular tourist spots, such as summer in Miami, winter in Venice, or fall in North Carolina's Outer Banks, you'll likely find rentals at the last minute. Since there is plenty of supply and limited demand, many owners will knock off 10 percent or more for bookings made within two or three weeks of arrival. Ask for a discount even if the owner doesn't advertise one.
As a general rule of thumb, give yourself a month's time to search listings, contact owners, do more research, and negotiate. At the very least, you'll need a week to make all the arrangements.