Hi, we do three months, Jan, Feb, March in Florida and love it.
A couple questions first.
1. Do you want "community" life...lots of "older folks" getting together, drinks on the patio, golf with the boys, all retired neighbors, structured fun, ect. or do you prefer most activities alone or with any age.
2. Is "being by the ocean" a big deal...remember in the winter most ocean walks are with a jacket or even a coat and the water is way to cold to swim in. If you want community and ocean, our plan is not your thing.
I might catch some gentle ribbing about our winters, but we rent fully furnished 3 bedroom/2 bath home 2 miles from Disneyworld in a 50/50 owner occupied/rental community at a real bargain price. These homes are designed for weekly rentals but Jan, Feb, March the kids are in school and Disney World is slower. Community is totally isolated by a gate with huge lake and owner pays all utilities including pool heat for our winter. They love having guaranteed rental during "low"season and adults who care for the home and don't beat it up. Very nicely furnished, by the way, Cable TV in all bedrooms, leather furniture, nice silverware, dishes, linens.
My spouse (retired from U of Iowa Medical College Admnistration) works 2 days at week at Disney World and LOVES it. They pay her to be nice, do whatever the guest wants and she works indoors/ AC with other retirees and some local folks. He perks include free admission to the parks for her and our guests.
I work 2 days at "top 5 in Orlando" golf course as a starter and love it also. My Perks, free golf for foursome anytime (normally $135/pp in winter)plus minimum wage.
Leaves us 5 days to go the ocean, flea markets, and just explore central Florida. I just can't sit and be "retired" and the "Over 55" communities just do not appeal to us.
We have made enough new friends at Disney the golf course to do dinner once in while, especially at Disney specialty restaurants, but also like spending time alone.
We love having guests from up north for 2-3 nights a couple of times a month...we can keep them very busy in Central Florida and they always pick up the tab for lots of what we do and see....
Just a thought for you...rent for a year or two...turn key, never a worry about storms, insurance, bugs, thefts, mold, lawn care, ect.
Good Luck...Ted