Start as a co-host and work under a vacation rental management company in the area to learn the ropes.

Airbnb already became a synonymous for family vacation.

I would like to buy a future retirement home to get away from the cold winters but in the meantime would love to rent it out as a vacation rental.What are the good areas to consider and where would I get the most vacation renters and cash flow?

My wife and I live in Chicago and vacation in San Diego every year.  

There are some New programs coming for 2025 for primary homes, Vacation homes, and investment properties.

I also got a written and signed agreement from tenant that is notarized for him to vacate on or before 2 weeks deadline after closing. 

They are coming to your property if you allow them or not (you cannot forbid service animals) Consider the facts: https://www.dogster.com/statistics/pet-travel-statistics-tre....Top 12 Pet Travel Statistics78% of American pet owners travel with their pets each year.54% of cat and dog owners plan to travel with their pet.58% of people would prefer to travel with their pet over a friend or family member.52% of travelers base their travel plans on accommodating pets.About 75% of luxury, mid-scale, and economy hotels allow pets.In 2019, a total of 404,556 animals were transported by airline.Nearly 64% of travelers prefer to travel with pets by car.42.9% of people look for a destination with hiking and fresh air for pet travel.Dogs make up 58% of the pets traveling around the world.37% of owners take shorter vacations because of their pets.10% of travelers have hidden their dogs to travel.27% of dog owners go the extra mile for their pets.

My company also offers premier vacation rental management services as we recently expanded our services to MTRs because of the apparent need for management services in the sector.  

All are local to me in a non-vacation rental spot.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.