Short-term rentals in Winter Park, FL

[Jaclyn38]

Hello Winter Park, FL Hosts-

We’ve been hosting in Winter Park for about a year and have just recently received a notice from the city saying we need to shut down our short-term rental. City rules require we change our listing to a 27-day minimum rental, which we just did in order to comply and not get fined. However, we are looking to fight this. 

has anyone else received this notice and had success in appealing to the city?

I called the city and they said this notice wasn’t just sent to us, but they’re cracking down and sending it to every host in Winter Park. 

I would love to get a group of us together to appeal to the city commissioners to meet us in the middle somewhere. 

AirBnB is collecting occupancy taxes that should be going to the city, so they’re making money on these listings as well as the local businesses.

These are all people that want to stay in and spend their money in our local shops and restaurants, but can’t afford the high priced ticket to stay in a local hotel. Our home offers an option to them. 

I’m interested to hear what you’ve all heard or if you’ve been able to work with the city on your listing. 

best,

jaclyn

[Caitlin295]

** if you are interested in class action. 

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[Jalal25]

You are brave and we all stand behind you in this cause. Thank you for fighting for the neighborhood rights 🙏🏾🙏🏾🙏🏾

[James2695]

Any updates on this matter would be greatly appreciated.

[Jalal25]

Hey I had to take down my Airbnb, they didn’t even give me a choice. However I do have a Karen in my neighborhood that hates me. If 27 days  is requirement to keep it up then I’ll start again. 

[Helen3]

Surely you checked with your local government to see if there were STR restrictions you needed to meet, in order to set up your STR business  @Jalal25 

You can't blame someone else if you chose not to comply with local STR regulations and have been asked to stop hosting as a result.

In general it's always better to get neighbours on board, it makes things much easier for all parties concerned.

[Michelle787]

@Jaclyn38 I know this post is a few years old but while traveling, now, I received an email from the city stating that I was in violation of the short-term rental having my property listed for 28 days. The message stated that I had a final inspection and was found in violation. I had the person who has been checking my mail go by and a letter had been sent stating that my property needed to be listed for 30 days or more. This is a change from the previous messages I had received.

I have sent a message to the city requesting when the change to 30 days or more was made as the bylaws State for one month or more and I was told that since February was the shortest month it was 28 days or more. Has anyone else received any letters or emails regarding this? September 2024.

[Jordan1140]

Hi @Michelle787 and @Caitlin295 I am curious to know the outcomes of your conversations and actions. This is May 2025. I've also updated my profile to be in compliance but am still receiving letters stating I'm not in compliance because my profile is active. I don't want to take my profile down because a) that's alot of work to build and b) if the policy ever changes I'd like to keep my reviews that I worked hard for. 
Would anyone like to sit down with the commissioners and have a discussion? I'd really like to think through this thoughtfully with other hosts and if we can create dialogue to create change. 

[Michelle787]

Hi Jordan. I found the post. I'm available on WhatsApp if you'd like to discuss this. **. Back in the UK so I can't answer calls but I can text

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