Short term vacation rental out of state management? SW Florida

[Alex Smith]

Hello everyone, my father purchased a sfh near the beaches in Florida. Closing is in 30 days, its turn key, ready to be rented as is. At first we were going to use a property management company to handle the rental, but have since started to reconsider handling the management ourselves. It's tricky with us being out of state, so I was hoping to get some insight from those of you that have something similar. This will be a short term rental marketed through vrbo, air bnb, booking.com, and trip advisor (those are what we plan on listing through so far). How do you prevent the calendars on these websites from overlapping bookings?

The most important systems we've realized a need for with managing this ourselves would be a housekeeping/cleaning service that would be able to clean and ready the home for the next guest as well as a local host or someone we can have check in on the home, assist guests if they needed someone in person, check over contractor work, etc. Does anyone have any suggestions for these in Naples Florida? How have you all implemented payment for these services? By use? Monthly?

How about rental contracts? How did you set yours up? Rental Policies such as cancellation, smoking, pets? Any reason not to go with rental insurance instead of a security deposit?

Any suggestions for a reliable/trustworthy general contractor out of Naples Florida?

If there is anyone here running a short term rental out of state I would love to chat with you regarding how you are handling and managing the property. Lots of moving pieces with something like this out of state.