I always do it myself.
For airfare I usually start watching prices as early as possible and strike when I think they are best. For instance, I usually fly from Fort Lauderdale to Washington DC for an average of $70 each way on Jet Blue -- direct flights.
For hotels I usually go with Hotwire.com as their stars rating is pretty accurate and you won't find one of their four star hotels in a shitty neighborhood.
For cars I always book right on Enterprises site as they typically have the best deal but also sometimes the airlines have a car upsell that is cheaper so I get the Enterprise price direct first and then compare. If I'm also booking a hotel on Hotwire I will see what their rates are as well.
I think doing all of that is fun.
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