A 51-year-old Airbnb host at a family-friendly Florida resort near Disney World now faces criminal charges after witnesses captured him on camera performing a sex act with a vacuum cleaner in a shared outdoor space, capping weeks of complaints about his nude wanderings through the property.
Story Snapshot
- Kevin Dale Westerhold arrested January 27, 2026, charged with exposure of sexual organs after witnesses recorded him engaging in sexual acts with a vacuum cleaner outside a Windsor Hills Resort residence
- Residents reported similar behavior since December 2025, including nude appearances in shared hallways captured on Ring and Blink cameras throughout the resort
- Westerhold and his wife operate multiple Airbnb rental properties within the same resort community where the incidents occurred
- Osceola County Sheriff’s Office actively seeking additional witnesses as investigation continues, with Westerhold booked into Seminole County Jail
When Vacation Rentals Become a Nightmare
Windsor Hills Resort in Kissimmee markets itself as a prime vacation destination steps from Disney World, where families rent townhomes for magical getaways. Kevin Dale Westerhold understood this market well. He and his wife hosted guests through Airbnb at properties on Grassendale Street and Almaton Loop within the resort. What guests booking those properties did not know was that their host allegedly spent his free time wandering the shared spaces in various states of undress, behavior that would eventually land him in handcuffs.
A Pattern Emerges in Shared Spaces
The trouble started quietly in December 2025 when residents began reporting concerns to the homeowners association. Someone matching Westerhold’s description appeared partially clothed or completely nude in common areas. The HOA received video evidence confirming these complaints, but the behavior continued. On January 21, 2026, a Ring doorbell camera captured footage of a nude male in a shared hallway. The next day brought the incident that would trigger law enforcement action when witnesses observed and recorded Westerhold exposing himself and engaging in a sexual act with a vacuum cleaner outside a Grassendale Street residence.
Multiple Cameras Tell the Story
The strength of the case against Westerhold rests on video evidence from multiple independent sources. Witnesses captured cell phone footage of the January 22 vacuum cleaner incident. Ring cameras documented hallway exposure. Blink security systems from properties on Almaton Loop corroborated the pattern of nudity in shared spaces. When Osceola County Sheriff’s deputies arrived at the scene, Westerhold had already fled. The investigation connected the dots between the various reports, leading deputies to identify the suspect and coordinate his arrest with the Oviedo Police Department.
The Airbnb Equation Nobody Calculated
The peer-to-peer rental economy thrives on trust between strangers. Hosts open their properties to guests who rely on reviews and platform vetting. Guests assume the person managing their vacation rental operates with basic decency and respect for community standards. Westerhold’s case exposes a vulnerability in this system. He was not just a resident engaging in bizarre public behavior. He was actively profiting from the same resort community where he allegedly created safety concerns for families and neighbors. The disconnect between his professional hosting persona and his alleged personal conduct raises uncomfortable questions about accountability in short-term rental platforms.
Legal Consequences and Community Impact
Westerhold faces charges for exposure of sexual organs, a crime that carries potential jail time, fines, and possible sex offender registration depending on conviction and sentencing. The Osceola County Sheriff’s Office continues urging anyone with information about additional incidents to come forward, suggesting investigators believe the documented cases may represent only a fraction of his behavior. For Windsor Hills Resort residents, the arrest brings relief mixed with lingering unease about safety in spaces designed for families. The incident casts a shadow over the resort’s reputation as vacationers inevitably wonder what other surprises might await in communities where hosts and guests intermingle.
What This Means for Vacation Rentals
The hospitality industry already grapples with questions about regulating short-term rentals and ensuring guest safety. Westerhold’s case adds another dimension: what happens when the host himself becomes the hazard? Platforms like Airbnb conduct background checks and maintain review systems, but these tools cannot predict or prevent bizarre criminal behavior in shared community spaces. His arrest occurred near his Oviedo home, miles from the resort properties he managed, illustrating how hosts can maintain distance from their rental operations while still impacting those communities. The case underscores the need for property management companies and HOAs to maintain robust incident reporting systems that bridge the gap between community concerns and law enforcement action.
As Westerhold sits in Seminole County Jail awaiting further legal proceedings, the families who vacation at Windsor Hills Resort and the permanent residents who call it home are left processing an uncomfortable reality. The person profiting from their community’s appeal as a family destination allegedly treated shared spaces as his personal playground for exhibitionism. No trial date has been set, and the investigation remains active. For now, the vacuum cleaner incident stands as a cautionary tale about the hidden risks lurking in vacation rental communities where financial opportunity and personal accountability sometimes fail to align.
Sources:
Man arrested after engaging ‘in sexual performance with vacuum cleaner’ at resort: cops
Man arrested performing sex act with vacuum cleaner at Kissimmee resort, officials say
