I want a vacation rental for my family?

Certainly wood doesn’t say recently vacated but boxes might. 

I'm concerned that if I bring up the matter of withholding security deposit to cover the costs , they might cause more damage to the house prior to vacating this month. 

Park most of it in a 4.5% saving account right now, and then I'd take one of two tracks.STR/Vacation rentalTake some of it and buy a nice vacation rental/STR in a mid-size market (like maybe not here in Colorado where you're looking at $100k outlay on the low end). 

My lease tells the tenant they should let me know if they are moving out at the end of the lease 60 days in advance, and that I intend to give them a formal 30 day notice to vacate the premises when we're 30 days from the end of the lease.

My siblings and I are interested in partnering to purchasing single family vacation rentals in Aruba. 

All these folks these days bragging on their Instagram and Facebook showing their nice houses their latest car constantly posting their vacations etc etc..

This is a delicate situation and I want this to be as smooth as possible, having them vacate the property is a last resort option. 

Mostly part timers and vacation homes at the time. 

In our opinion, the only feasible way to do this job would be if the house were vacated and a major renovation were to occur at which time we could run new gas or electric line, trench the slab and run new drains for T&P and pan drains.This tenant will need to move due to it being unsafe.