First thing I’d tell a neighbor is to pull the HOA documents before you do anything else. If the place is in a community with a homeowners association, the rules on short-term rentals are usually spelled out there, and they can be stricter than what the county allows. Some associations cap how many rentals you can do a year, some require a minimum stay, some have stopped new short-term rentals entirely. That matters whether you’re still renting it out or trying to sell it, because a buyer is going to ask. Get the covenants, the current rules, and any recent board minutes in writing. If the language is murky, that’s a lawyer question, not a guess.
The county or city matters too. Rules on vacation rentals vary a lot across Central Florida, and they can change. Call the county or the city and ask what applies to that specific address. Don’t rely on what a neighbor told you two years ago.
Selling furnished is often the easy part, especially near the parks. Buyers looking at vacation property frequently want it turnkey, so a furnished sale can be a selling point. But be clear in the listing about what conveys and what doesn’t. Make an inventory list. Personal items, linens, electronics, that stuff adds up and it’s where deals get messy. Decide early what stays and price accordingly.
Managing showings from far away is doable but you need a plan. A local agent who can let people in is the simplest route. If you’re still renting the place, you’ve got to coordinate around guest bookings, and that can get tight. A lockbox or smart lock helps, but check with your agent on what’s allowed. Keep the place photo-ready between guests, because a messy rental kills showings. And be honest with your agent about your schedule so nobody is surprised.
On taxes, bring a list of questions to a CPA who knows Florida rental property. Ask about depreciation you’ve taken and what happens when you sell. Ask how the property is classified for tax purposes and what that means for your situation. Ask about the homestead question if it ever applied. Ask about state and local taxes on rentals and whether you’ve been handling them right. Ask what records to keep. These answers depend on your facts, so don’t take them from me or from a forum.
One more thing. If the property is held in an LLC or with someone else, or if there’s a mortgage, get the lawyer and the lender involved early. It’s calmer to sort that out before a buyer shows up than after.
More detail for Orlando sellers is in vacation home sellers near the parks.
