Answering your question, a suggestion for good location will be Miami Beach, or Fort Lauderdale.
Both are places with high demand for rental units, all year around, so you have the option to rent the unit in high season for short term at high season price or long term, at regular price.
In the high season, there is not enough rental units available on this areas so prices are higher.
You can buy a studio or in few cases a one bedroom apartment on those areas for 100K or less.
Easy handle condo will be determine by the age and conditions of the building and unit, however most condos in Miami Beach and Fort Lauderdale are a few years old and need constant maintenance.
I work mostly with foreignes looking for rental options in South Florida and I will be happy to answer any further questions to help you decide wich will be the best option for you in this market.