Hi Katie,
I am also from New Hampshire, sold my house and moved to The Villages at the end of August, 2012. I found a long term rental, but, it took me awhile to find something I could afford.
According to your notes, it appears you want to rent just in the winter. My suggestion would be 1. Check craigslist, Ocala fl and look for share rentals in the Villages 2. Put an ad on Craigslist. 3. Look for homes4rentthe villages.com or homes to rent by owner. I have found the longer you rent the cheaper it could be. There is also a club called the Sumter Singles, you may be able to find someone who would rent to you..
Good luck
Sue
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