Naples, FL
It's not unusual to find Naples natives with a home office here and a corporate office elsewhere. This city near the Everglades is a snowbird destination - the population jumps by as many as 10,000 people in the wintertime.
This is a town where many homes have docks in the back because so many locals enjoy the boating and fishing in the area. For the well-heeled residents who want to winter here, telecommuting is key.
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Last updated July 16 2008: 1:27 PM ET
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