Renting first in a good idea. We did not do that and we have recently sold the beautiful little home we bought last Nov and purchased a bigger home. We loved the location and the house but decided we needed a bigger garage.
On another note, we have a nice 2/2 Cottage home in the Village of Duval available for rent for the months you are looking for. Duval is centrally located close to Colony Plaza, the new Pinellas Plaza which will be open by your timeframe, Lake Sumter Landing and Brownwood. A golf cart is included. Please see the link below to view the property.
Duval Vacation Rental - **** 474120 - 2 BR The Villages House in FL, Elegant 2 Bedroom/2bath Cottage with Golf Cart & Wifi in Duval