Yes, there is a video post referenced further up on this thread (you should watch that whole video, I go into great depth on it) - but there is also a graphic here as well
This is the “good stuff” of SEO 
Think of the pillar concept like there is one main structure, and in order for it to be weak supported and strong it needs a bunch of supporting structures (some people call this the spoke and wheel) concept is the same.
As I dig into your content more I actually see you are doing a great job creating multiple pages that are specifically targetted:
But let’s just pick one and make it a pillar (meaning we really want to rank tops for it and will build supporting content to achieve that result:
Let’s take Park City:
First, I would like to recommend that you separate Park City and Deer Valley into unique pages, as each is competitive enough on it’s own to have it’s own page.
Anyways, let’s say we are determined to rank #1 for Park City Ski In Ski Out (or better yet, Park City Ski properties)
You would have your main page:
Title: Park City Ski Properties
Filename: /park-city-ski-properties
And then all the on page optimization would be related to Park City and Ski properties (you would not dilute it with Deer Valley, or condos etc)
So that is your “main pillar”
Next you need to create “sub pages” (you already have several of these, you just need to link them together properly and ensure they are optimized properly. An example of this would be “park city ski in ski out condos” (great sub page, not as competitive, related to the main topic, very supportive.
You also have ski in ski out land as a sub-page (only referring park city << NOT deer valley which is separate as a keyword)
And then you’d create hyper-specific blog posts that are super interesting about ski in ski out properties, but specifically in relation to park city.
How you link them together is important (you should be using contextual links, not cannibalizing your other pages or diluting your keywords etc.
That’s why it’s important to reach up on other threads on pillar pages, but most important, what the video here’s the link for that Creating Content Clusters & Pillar Pages For Real Estate SEO