How to choose who you rent from.

The Three Kinds of Company

Almost everyone selling you a Tuscan villa is one of three things, and the difference decides what happens when something goes wrong.

Marketplaces list tens of thousands of properties nobody at the company has seen. They take a fee from both sides, the photographs are supplied by the owner, and the review score is doing all the quality control. They are genuinely the right tool if the priority is the widest possible choice at the lowest possible price, and they are the wrong tool at €30,000 a week, because the thing you are buying at that price is judgement and there is none in the transaction.

Brokers resell another agency's inventory. This is why the same villa appears on nine websites at nine slightly different rates, and why the person answering your email may be two companies away from anyone who has been to the house. Brokers are not dishonest by nature, but every additional link adds a margin and removes a fact, and when the boiler fails on a Saturday you find out how long the chain is.

Direct rental agencies contract with a small number of owners and know each house personally. The collection is small because visiting properties does not scale. This is what we are, and the honest trade-off is that we will always show you fewer houses than a marketplace will.

You can usually tell which one you are dealing with in a single email. Ask who owns the house and who issues the contract. A direct agency answers immediately and by name.

The Four Questions That Get Past the Photographs

Photographs are chosen to flatter and every agency has the same set, often literally the same set. Four questions get past them, and anyone who has actually been to the house answers all four without pausing.

Ask for the pool dimensions, not a photograph. A six-by-three-metre pool looks generous in a wide-angle shot and feels small at four in the afternoon with eight people in the house. Numbers cannot be photographed flatteringly.

Ask what is genuinely private and what is shared, in plain terms, including the drive and the land. A great many properties described as villas are one wing of a converted farmhouse, or one of five casali on an agriturismo. You will hear the next party. This is the single most common gap between the listing and the week.

Ask exactly which staff are included, and on which days. "Staffed" covers everything from a daily team to a cleaner on Fridays. Get it in writing with the days named, because it is the difference people notice most and complain about last.

Ask what the house is like in bad weather. A week with two wet days is normal in May and October, and some beautiful houses have nowhere to put twelve people indoors. If the answer is only about the view, there is no answer.

The Question Underneath: Do I Have to Give Up the Hotel?

Most people weighing a villa are really weighing a loss. A five-star hotel comes with a concierge who fixes things, a kitchen that opens when you are hungry, a spa, and somebody whose job it is to notice. Handing that up for a beautiful house in the hills is a real trade, and any company that pretends otherwise is not being straight with you.

The reason we say this on a page about choosing an operator is that it is a question of what a company can actually reach. Ask whoever you are talking to whether they hold houses on serviced estates, because that is where the trade disappears, and most cannot: those houses are not on the open market and are placed through a small number of companies the estate has worked with for years.

We represent villas on two of them. At Castiglion del Bosco, the Rosewood estate in the Val d'Orcia, a house such as Casa del Vescovo is entirely yours, with its own pool and its own gate, while five thousand acres of estate run around it, with the restaurants, the spa, the golf, the Brunello winery and a concierge. At Castelfalfi, between Florence and Pisa, the same is true of Casa Medici in the restored medieval borgo, with five restaurants and the estate spa a walk from the door.

The practical effect is that nobody in the party has to choose. The grandparents get the spa and a restaurant they did not have to book a car to reach; the family gets the long table, the private pool and a house with a gate. If you are being asked to give up hotel service to get villa privacy, you are being offered the wrong houses, not the wrong format.

What to Verify Before You Pay

Before the deposit: that you have a written contract naming the owner and the property; that the payment account is in a company or owner name you recognise from that contract; that the cancellation terms are stated in figures and dates rather than described; that what is included is itemised, with staff days named; and that any additional charges, tourist tax, heating for the pool, a security deposit, are listed rather than mentioned.

Ask for a video call from the house, or recent video walked by someone at the company. Not a produced film, a phone walked through the rooms. Any agency that has been there can produce one within a few days, and the request itself is diagnostic.

Ask what happens at eleven at night on a Saturday when something breaks. You want a name, a number and a person who lives within half an hour. If the answer is an email address, you have your answer.

The Test We Would Want You to Apply to Us

The only real test of whether the advice is advice or a sales pitch is whether the company will tell you a house is wrong for you, or that Tuscany is wrong for the week you have described, or that your budget buys something better in a month you had not considered. Everything else can be performed.

For what it is worth, our answers: we represent thirty-two houses, accept roughly one villa for every twenty we visit, and have been inside every one of them. We are paid by the owners, so the rate quoted is the rate paid and there is no booking fee at checkout. The contract comes from the owner of the house. We hold villas on two serviced estates, Castiglion del Bosco and Castelfalfi, which is where hotel service and a private house stop being alternatives. Our booking terms are published rather than sent on request, and what a villa costs gives real figures rather than "from" prices.

Where we would fail your test: if you want the widest choice, we are the wrong company, and a marketplace will serve you better. If you want to book in ten minutes without speaking to anyone, we are also the wrong company, because we answer every enquiry personally and that takes a day. We would rather say so here than after your deposit.

See also

• How renting works→
• What a villa costs→
• Villa or hotel?→
• The luxury collection→
• Our booking terms→

Frequently asked

What should I look for in a luxury villa rental company?

Four things settle it. Whether someone at the company has physically been inside the house you are considering. Whether they contract directly with the owner or resell another agency's inventory. Whether the rate quoted is the rate paid, with no booking fee added later. And whether they will tell you a house is wrong for you, which is the only real test of whether the advice is advice or a sales pitch.

Can I get hotel service and still have a private villa?

Yes, on a serviced estate, and it is worth asking any company whether they hold houses on one. We represent villas at Castiglion del Bosco, the Rosewood estate in the Val d'Orcia, and at Castelfalfi between Florence and Pisa. The house, its pool and its gate are entirely yours, while the estate's restaurants, spa, golf, winery and concierge run around it. Those houses are not on the open market, so a company either has the relationship or it does not.

What is the difference between a villa marketplace, a broker and an agency?

A marketplace lists tens of thousands of properties nobody at the company has seen and takes a fee from both sides. A broker resells another agency's inventory, which is why one villa appears on nine sites at nine prices. A direct agency contracts with a small number of owners and has been inside each house. At marketplace prices the first is fine; at €30,000 a week you are paying for judgement, and only the third has any.

What questions should I ask before booking a villa I have not seen?

Ask for the pool dimensions rather than a photograph. Ask what is genuinely private and what is shared, including the drive and the land. Ask exactly which staff are included and on which days. And ask what the house is like in bad weather, because a week with two wet days is normal and some houses have nowhere to put twelve people indoors.

What does a villa rental company on an estate give you that a standalone villa does not?

The things a house cannot hold on its own. A spa, several restaurants, a concierge, a golf course, a working winery and a doctor within reach, all a short walk from a private house with its own pool. It suits multi-generational parties in particular, because the people who want a hotel and the people who want a villa stop having to argue about it.

Should the villa rate include a booking fee?

There is no reason for one if the company is paid by the owners, which is how direct agencies work. A booking fee added at checkout usually means you are paying a second margin to an intermediary. Ask before you are quoted, not after.