I think this would prove to be far more difficult than meets the eye. As most gated communities have an HOA... Usual and customary practice dictate that an application is required to be submitted to the HOA. This can take a week or two to get approval... This alone may prove to be a stopping point if nothing else.
Advice.... Try single family without gated community and double check the HOA rules for any restrictions that may apply.
Gary Youngman (561) 306 - SOLD (7653)
Boca Raton Beach Office
There are mutliple communitites that allow you to rent a few times a year. Sea Ranch Club, Highland Beach Club, Courtside Villas in Mission Bay, Atrium Condo in Boca Raton, Breakers at Boca Townhome, etc. There are so many, and rules are always changing...so you would want to reconfirm with the Condo board and verify the rules on renting.
Please note that although there are many properties that allow you to rent, multiple times a year...there may be a rule that you can't rent the first year or two of owning.
Good Luck with your Investment Property!