Dynamic Lodging Prices in Florence

Interesting questions, and since I'm price obsessed (I travel a lot but only have a low budget) I can tell you my impressions.
1. October is the ideal time for a weekend in Florence for most Italians. This weekend is not: too hot still, and many are returning or have just returned from longer vacations at the sea or in the mountains.

As regards Booking.com:
2. Studying prices on Booking.com I've found that if you have nerves of steel and don't much care about the accommodation, you can book last minute and maybe save a lot of money. In my experience this doesn't work for weekends in popular destinations since lots of people can be tempted to have a last minute break. It especially doesn't work for small establishments with high ratings. They don't have last minute availability.
3. There isn't much difference between booking a lot in advance or 3/4 weeks in advance as regards prices. Remember that Booking.com guarantees to price match itself although I have never tried or needed to do that.
4. The best solution for me is usually booking in advance with free cancellation as close to the stay date as possible. Some people suggest booking with free cancellation actually planning to cancel if you find something better. Doesn't seem fair to me, especially for smaller establishments.
As regards Airbnb:
Airbnb hosts (I know because I am one), can opt in to Airbnb deciding prices. Since 'airbnb' prices are a lot lower than market value I can't believe many hosts do that.
Otherwise hosts fix the prices. Some may reduce prices last minute, but more likely a week or two before, not the day before. Many don't. But there's no algorithm. I've never found a last minute bargain on Airbnb.
Where else to look for accommodation? Google maps and thenthe website. Or use Google maps to find the contact details for the place you've found on Booking.com or Airbnb and contact them directly.
But don't hold your breath. Ive been quoted higher prices directly than on Booking.com. Instead if you can find the Airbnb hosts directly you may save.
But all the usual precautions apply. I wouldn't send substantial amounts as a deposit.....etc etc.

Hotels in Europe use dynamic pricing. For example. we wanted to spend the last week of September in Bologna and then the first week of October in Florence. I choose apartments in Bologna that were around 1000-1200 Euros a week in July when I started looking. for the time I needed they were 5000-6000. Same with hotels -- hotels that were about 150 were suddenly 500 or more a night then. So obviously something that puts demand on hotels is going on at that time. (September tends to be the highest cost month to book lodging in Paris and apparently also in Italy. In some place weekends are much higher than rooms during the week. This changeable cost has always been the norm for as long as we have traveled i.e. decades.

We aren't staying in Bologna this fall but went with a place in Florence we have used before and will stay two weeks there instead.

Last minute is usually the highest prices in my experience and early October is a high demand and costly time.

About three weeks ago, we booked 4 nights in April 2025 at an AirBnB apartment in Florence in the shopping district. For our time there (April 2-6), it's priced very reasonably. But...the original plan was for 10 days later, and being that much closer to Holy Week--FYI it was even higher in Rome--prices for the same apartment were about 25% higher. So yes, there is definitely dynamic pricing going on.

For what it's worth--I am also a host/owner of a Maine cottage that is advertised on AirBnB & VRBO. Originally I let my agent employ their own algorithms--dynamic pricing--but I found it inadequate as far as reacting quickly enough to market changes on a day-by-day basis. Thus, I make the changes myself, contact my agent who makes the changes with AirBnB & VRBO. Works better that way!

Also many accommodations put on booking.com only a limited number of rooms, so I use booking.com but also check their own website. I’m a last minute booker of hotels. I may search a hotel ahead of time, but then book it when I park in front of it, then walk in. When I say I book “last minute” I mean it literally .

Thanks for the replies. We've decided to take our chances like Roberto and book last minute. Hopefully we won't be competing with him for the same room ;)

There are very few occasions when a locality will be totally booked. It happens in Venice around Carnival weekend and at some other locations when there is a major event. For example in Rome if Easter falls at the end of April, near April 25 and May 1, both holidays. But in most cases there will always be availability somewhere. I usually check the availability for the day I expect to go there. Sometime I book it when I stop for gas just minutes before arriving. In the last two years I check the availability in booking, then drive to the place I like that is available on booking, park in front of the hotel, walk in and ask if they can show me the rooms and give me a better deal than what they are showing on booking. They always do. And sometimes (including last June at the Argentario) it is a nicer room at a better price that they don’t even put online. In Lisbon I booked WLP hike I sat at the desk. I asked their price, we together checked on booking.com, then booked at the better price (in person or booking) and they always gave me whichever best deal was available.

I have been tracking hotel prices on booking.com for about 2 months. They for sure are using dynamic pricing, at least from what I can tell. What drives me up a wall is if I cancel a reservation and immediately see if listed for hundreds of dollars more than what I booked it for. The whole pricing scheme is aggravating. I truly hate dynamic pricing.

Fun thing I learned the other day as I was evaluating the cost of my accommodations: despite booking from the US and the price showing in US dollars, the fixed price of what you book is actually in euro’s. But since the value of USD to EUR changes daily, so does the US dollar price. My accommodations that I have already booked have been fluctuating in (US dollar) price daily! Took me a minute to understand why that was happening haha