Florida and whatever county you are in (Sumter, Lake or Marion) have a hotel tax - in Sumter the combined tax is 9%. You file it monthly (online) if the rental period is less than 6 mos. I rented my CYV out for over 4 years, averaging 6-8 mos every year, including some summer months/weeks.
I used vacationrentals.com and also thevillages4rent.com the last year. A friend who bought 2 years ago (both of us needed tax deductions and looked on our villas as future homes) says she is now getting the vast majority of her inquiries from thevillages4rent.com. I think it is becoming well known and probably pops up in searches. Not sure it was out there when I started renting. I got inquiries from both. Also repeat tenants.
Do not rent Feb. or March until you have January rented, or included. You could rent March by itself about 100 times. Having a golf cart was the key to renting it more than just Jan-Feb-March. Also high speed wi-fi internet. I didn't the first year and I rented it only about 5 mos.
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