I am so sad. We stayed at the J&J Historic Hotel in Florence 5 years ago and I so wanted to stay there again. It is a beautiful, unique hotel converted from an old convent I believe, but sadly it is not available in October this year. Does anyone know of a hotel in Florence similar to this? Outside courtyard is a plus. Thank you.
This is not a well-informed reply but decades ago I stayed in a very popular superior tourist-class "classic" in Florence called the Porta Rossa. Every room was different and on the large size. it's been completely renovated by the NH chain, and I think it's now called the NH Porta Rossa, but you might see if it meets your needs.
We enjoyed the Hotel Balusteri, which is on the Arno.
Sorry, it is Hotel Balesteri.
https://www.tripadvisor.com/Hotel_Review-g187895-d203902-Reviews-Hotel_Balestri-Florence_Tuscany.html
We've stayed at the Hotel Palazzo Guadagni twice and been very happy both times. Historic building, beautiful frescoed ceilings in many rooms, in the Oltrarno. This won't be relevant for you in October, but we were very happy with the A/C when we visited in June. No courtyard, but there is a lovely loggia/terrace. https://www.palazzoguadagni.com/