I've refined my question a bit more which I hope will help the community in giving me some help. I am spending 2 months next April/May 2026 in Italy. I've narrowed the area down to around Arezzo, Sienna, and Pescara. I know Pescara is quite different than the other two, but any of these will work. I would like to book directly rather than going through the usual search engines or travel sites since I 'hope'! to get a monthly price for the extended time, rather than a nightly rate. Would like a private small villa/house near a small village that is walkable, but also affords quiet and privacy; some surrounding land; hopefully some views; and pool would be fabulous! close to rail; 3 bedrooms as family will be joining us for some of the time. Does anyone have a good experience with any agritourismo, small house rentals, and direct booking? Links to their websites would be super and/or contact info please. Thank you all in advance! (p.s. I'v been using Rick Steves books and travel info since the 1970's and have never been steered wrong!)
Posted by
6137 posts
One strategy that may help: I find when I am searching for accommodations (usually Booking.com) that sometimes agencies show up in the results--then I google those agency names and can contact them directly. You could use a site like Booking to see what kinds of things are available and what to expect, then seek out alternate companies. There is often a good deal of overlap as local agencies share their listings.
Also, don't forget to just google it! ("villa rental in Pescara" for example) That can be a lot more quick and direct than waiting to find someone who knows exactly what you need on a forum. Be sure to turn off the AI results (click on "web") for best results.
Posted by
San Diego, California, USA
1664 posts
Hello Lucy, in 2024 I spent 2 months in Italy and one month only in Lucca to test out "small town" life. I have also spent time in both Siena and Arezzo but not in Pescara.
Will you have a car? Not having a car is going to tightly restrict your proximity to a specific town that will then have transportation options.
AirBnB has sucked much of the oxygen out of the longer term rental market in touristy areas of Italy - and probably many places. Previously there were realtors who built careers out of doing longer term rentals when many Americans were still doing tours. But as much as I tried I couldn't find any functioning "mom and pop" rental agencies in Lucca. I found several that I got no response from and some that were now real estate agencies and would have been happy to sell me something but weren't doing rentals. Even when I reached out to a real estate agent who wrote about rentals in Lucca he referred me to their "rental specialist" and she just sent me AirBnB links. AirBnB does offer decent month long discounts on many of their places but it is off their already high prices.
Siena is so fully touristy I would be shocked if there were still mom and pop places rattling around if you don't already know about them. If you are willing to have a car in stay in the areas around someplace like Siena then there may be other options. I have flagged the area around Buonconvento as well placed. Close enough to Pienza and surrounds and has 30 minute bus/train service into Siena as well. Arezzo seems much more likely as a place that's less touristed and may still have random rentals kicking around.
We rented a cute little place near our friend's place in Verona and when I mentioned it our landlady she said "Have her contact me directly." obviously interested in cutting out the web service and probably establishing a cash price. So the desire is there but it's hard to arrange from across the ocean and you don't have any kind of an "in". She was clearly ready to give a local with a reference a much better price than a tourist. If you can get the address of a place from one agency always try just searching address and see if it's on other sites for less money or with more direct contact information. AirBnB only wants you to communicate through their app for a reason.
When you're going to two months do your best to make sure you're not staying over some big holiday or celebration. That will make renting over that week or weekend harder. It sounds like you will be there over Easter but I was thinking of a big local festival like the Joust in Arezzo or the Palio in Siena.
Also how is your Italian? Italian proficiency drops off rapidly when you move outside of touristy areas. I do believe you can get by in Italy with a small number of well chosen words because if you want to buy or get something they will work with you to get things done. However it becomes limiting when you can't understand that they fruit and veggie guy is telling you which things you can pick for yourself and which ones they need to get for you and you're not getting any of it. Also Italians love to talk but if your Italian stops after "Che bel tempo oggi, vero?" it will limit your ability to engage with the people around you.
We had a wonderful experience - hope you have one too,
=Tod
Posted by
North Italy
572 posts
About longer term rentals and booking directly in Italy.
I usually look through Airbnb or Booking.com to find some rentals I like and that have many excellent reviews (usually means they'll be reliable if you contact them directly). Then:
1. Now all holiday rentals have to have a code number called a CIN
You will find this somewhere on the Airbnb or Booking.com listing.
Find the CIN and put it on Google, or wherever. This will bring you up all the places the rental is listed. If you're lucky it'll be on subito.it which has direct contact details, or on one of the many other minor websites which have direct contact details.
2. If you find somewhere you like on booking.com there is also the address. Go to that address on Google maps and you may find a listing with contact details of some type.
Another option on Google maps - choose your area/city and go through it on google maps searching for apartment or 'residence'. Follow up by clicking on the name - you'll get the google listing or maybe a website or at least a name to look for.
This will all take some time - but you'll end up finding somewhere nicer and cheaper.....
Arezzo and Siena will already be high season in April and May because of Easter and the long weekends around the public holidays on 25th April and 1st May. They are popular destinations for Italians on a short break or a long weekend, as well as school trips.
You may have a lot more choice and find it quieter in Pescara.