Hi BP Fam - while researching STR in Orlando, I created a summary of some key neighborhoods, criteria and helpful links. I am sharing this with the community as others may find this useful.
Please feel free to add or critique in comments. 

Good Neighborhoods for STR :
Champions Gate (17 min / 12 miles)
Celebration (12 min / 6 miles)
Windsor Hills (14 min / 5 miles)
Kissimmee Area (Storey Lake) (26 min / 14 miles) - Not all communities allow STR
Davenport (Town) (33 min / 18 miles) - Many communities in Davenport allow STR but not all
Solara (22 mins / 13 miles)

STR Not allowed in these neighborhoods (as of writing this post):
Windermere (18 min / 10 miles)
Harmony (17 min / 12 miles)
Winter Gardens (26 min / 13 miles)

Notes and Criteria:
- there may be STR restrictions by Orange County so research before investing
- Any property zone for STR is going to have an HOA that allows it. You only want to be in communities than allow it
- closer to Disney is preferred (15-30 min drive)
- Updated decor increases desirability (Disney themes)
- Preference given to larger homes (3+ bedrooms) vs. townhomes
- Games room (arcade and other equipment, sound and lighting)
- Pools are preferred
- If you're buying in community with HOA, check STR rules and any other costs
- invest in good photography to make your listings stand out

Helpful links:
COMMUNITIES ZONED FOR SHORT- TERM RENTALS IN KISSIMMEE, FLORIDA (thanks to @Valentina Naumenko)
https://www.biggerpockets.com/...

LOCAL MEETUP
https://www.cfri.net/default.a...

Thanks for insights provided by experts in the area:
Mike Shulman @strrealtor (Realtor)
Alice Horn @aliceh27 (Property Manager)