Serious Safety Issues and No Help After a $2,000 Loss
I am writing this review to warn other travelers about my extremely negative experience with Upstay, a company located in winter garden that was managing the property I rented in 1384 peaceful nature Way Clermont, Florida.
Before booking, it was absolutely essential for my family that the house be located inside Windsor Cay, a gated community known for its safety, clubhouse, gym, water park, and overall excellent infrastructure. I asked twice before booking whether the property was inside Windsor Cay in Clermont, and both times I was told yes. Based on that confirmation, I proceeded with the reservation.
However, upon arrival, I discovered this was not true. The house was located on an open public street, not inside any gated community, with no security, no amenities, and in a very isolated and poorly lit area that felt unsafe. Since I had already paid and had no alternative accommodation, I had no choice but to stay. This was clearly misleading information that influenced my booking decision.
The situation became much worse afterwards. Because I believed the property was inside a secure community — as I had previously stayed in Windsor Cay without issues — I had a valuable package sent there from The RealReal, containing two designer shoes worth over $2,000.
The property manager initially confirmed that the package had arrived and said she would hold it for me. She arranged for my friend to pick it up in the evening, but when my friend arrived at the agreed time, there were people in the house and lights on, yet no one answered the door.
The next day, the manager started making excuses, claiming the guests were out all day and it was difficult to arrange pickup. Eventually she told us to come back at 10 a.m. My friend returned as instructed, but the package had disappeared.
The house has a camera directly facing the front door, and the manager was clearly able to see and speak to visitors through it — she spoke to my friend through the intercom both times she visited. When asked for the date, time, and footage showing who took the package so that I could file a police report, the manager refused to provide anything and stopped responding entirely. She has ignored all further communication from me and from my friend.
As a result, I was left with a loss of more than $2,000 and no support whatsoever from the property management. Their refusal to provide basic information or cooperate raises serious concerns about their professionalism and transparency.
I strongly caution anyone considering booking with Upstate to verify all property details very carefully and be aware that, in my experience, they provided misleading information and were completely unwilling to assist after a serious incident occurred.