Most residential areas can only rent monthly or 28 days, meaning the owner can only rent the home out 12 times per year. This means about 5 months of income-Jan-Feb-Mar and July-August. There are some April and June monthlies.
*Ask your REALTOR if there are any Condos or areas that do allow weekly rentals as this will definitely be your best return.
As to what is the best rental situation, that is size, which areas, views, pools, how water and boating accessibility affects rental amounts and the typical rental amounts for both long and short term, plus the fees involved, ask your agent.
As to extra costs and what is necessary to have a Home as a Rental.
When you rent your home out you generally need to license it through the County. This costs is typically minimal and your agent’s company should be able to handle the paperwork for you.
The County and the Tax people want the homes licensed so they know where there may be tax dollars coming in. When your home is used as a rental, in effect you are operating the same as a hotel or motel and so they come under their safety guidelines.
This applies to the Keys but may be the cases statewide:
Every bedroom and the main living area must have a hardwired smoke detector and there must also be an escape light. This light comes on in case of a power outage-this also must be hardwired. (About $450.00 installed smoke detectors and escape light for a 2/2)
There also needs to be a professional quality refillable fire extinguisher that is approved by the fire department (about $55.00). This would be the same as you'd find in a restaurant or hotel room. There needs to be a dead bolt on the door that works from the inside and is a different key than the main door. All of these issues help protect your liability in cases of fire/break in.
When the home complies with all of the above and your agent has a signed contract from you authorizing them as a rental agent, then it can go into the rental pool.
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