STR (AirBnb/VRBO) Orlando—First Time Investor

[Katharine G.]

Hi all!

NY based investor looking to get a vacation home in Florida (tale as old as time, right?) and seeking some wisdom for a rookie.

Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.

Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.

Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.

Other than reading for my life, how can I number crunch and prepare for this? (Tricky to do now, especially) Anything you’ve done in this market that you wish you’d known about?