Population: 363,922
Share of population age 60+: 38%
Median monthly mortgage cost: $1,787
Median monthly rent: $1,228

While more expensive than many other Florida cities, many retirees appreciate the high quality of life. Residents of Naples report the highest sense of well-being in the country, according to an annual Gallup survey. People in this south Florida city say they enjoy supportive relationships, like what they do each day and have a secure economic life. Naples also scored highly on the desirability metric, and travelers and retirees are often drawn to the white-sand beaches along the Gulf of Mexico, the spacious golf courses and the mild winter weather.

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*Statistics and pictures provided by: U.S. News & World Report