Looking for STR Community in Orlando – Pool Homes with Amenities

[Fab Ragh]

Hey everyone, I am looking for insight on STR-friendly communities with pool homes and strong amenities that make renting easier .

I’ve stayed at Windsor Hills before and liked it, but unsure if buying there is a good idea due to its age. I’ve also heard of Windsor Cay and am interested in newer communities with similar features.

Does anyone have experience with these communities or recommendations for others that perform well as short-term rentals? Looking for something with strong occupancy potential and resort-style amenities.

Looking to network as well with locals experts and agents specializing in STR in Kissimmee, Orlando area.

[Andrew Street]

Hey Fab - I totally get the appeal of STR-friendly communities with resort-style amenities—having strong features like pools and clubhouse access can make a big difference in occupancy rates. I've also looked into Windsor Hills and Windsor Cay, and while Windsor Hills has great demand, I can see why the age of the community might be a concern. Newer developments with similar amenities could be a great alternative.

I’d love to hear what others have to say as well. Would love to connect and share insights!