Reputable villa representative

Many full time rentals all over the world are operated through a property management company, not directly by the owner. The owner hires a company to handle the reservations, cleaning, maintenance, etc. You might actually be better off going through a property management company that handles all three villas, rather than three separate owners. Or maybe they have one compound that will house the entire group. Most listings will show who the management company is. If you find that company listed over and over, find the company’s website and contact them directly. You’ll probably get a better rate, and can speak to an individual directly to find villas appropriate for your group. You could also visit the local tourism office website. They usually have links to recommended rentals.

Different platforms, different costs for the same accommodation is common. It would look more suspicious if they all cost the same to me. Airbnb are usually the most expensive, often by 20%.

The platforms charge you a fee as they handle payments and protect your money. They pay the accommodation different rates too - I am currently in Spain and the owner of this property gets paid less by Airbnb then VRBO of the published rate. There is also the issue of currency conversion rates changing.

I look at VRBO, Trip Advisor Rentals and Booking.com and opt for places that have reviews going back several years to ensure it’s a genuine place. I have never had an issue with bogus properties and pre Covid, would usually rent 3-4 properties a year on this basis. A local agent is no more likely to be reputable than one of the bigger platforms.

I have used Tuscany Now & More, and had a great experience with a villa in Umbria. I have a close friend who had to delay his booked villa reservation, and they have continued to be responsive to his efforts to rebook a complicated family trip. They have exclusive representation for the villas they show, and they have villas in all three areas you mention. I have recommended then to others who have also been satisfied. They’re based in London. Worth a look any way.

We found a company that has exclusive listings for villas and apartments in their area, Chianti and Florence. You will not see their listings anywhere else and they know their properties well and can answer specific questions about each property. We had an excellence one week rental experience for our large family group. Chianti dash and dash more dot com. Based in Panzano, between Siena and Florence.

Exactly, what are you needs? Six to eight bedrooms villas will be hard to come by and three of them together and in three different locations - real challenge. You might look at larger Agriturismos.

There are some other issues you need to be aware of, as well fraud. Some years ago, a friend rented a large villa in Tuscany from a very reputable management company. It was part of a newly redeveloped abandoned agricultural property; and, I believe, we were the first guests. There were a number of glitches, like the promised welcome food basket was missing and promised recreation facilities were unfinished.
The worst issue was that though the property appeared to be reasonably close to a decent size town and the A1, it actually required 40 minutes of driving to get there. We had to navigate, mostly in 1st gear, a long, unpaved road, full of potholes and ruts, from the villa to the state road. Then, another 20 minutes of driving was needed to reach the autostrada. The extra 80 minutes rt of driving for day trips got very wearing.
My advice, after that experience, is to do your due diligence on the reputability of the management company; but also read reviews by people who have stayed at the property. No reviews, no rental.