
Montepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Infinity pool · Heated pool
Service: Daily housekeeping · Spa
A luxury villa in Tuscany is staffed, private, taken whole and has a kitchen a chef can work in. These 31 villas meet all four, from historic villas to countryside estates, and a private chef can be arranged at every one.
31 villas

Montepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Infinity pool · Heated pool
Service: Daily housekeeping · Spa

Lucca & Garfagnana · 14 guests · 7 bedrooms
From €15,000 / week
Frescoed interiors
Service: Fully staffed · Private chef

Castiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Panoramic view
Service: Daily housekeeping · Spa

Chianti · 14 guests · 7 bedrooms
From €7,810 / week
Infinity pool · Panoramic view
Service: Spa

Lucca & Garfagnana · 24 guests · 12 bedrooms
From €23,200 / week
Wine cellar · Gym
Service: Fully staffed · Private chef

Castiglion del Bosco · 10 guests · 5 bedrooms
From €112,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Working vineyard
Service: Daily housekeeping

Chianti · 22 guests · 9 bedrooms
From €11,160 / week
Heated pool · Cinema room
Three separately restored stone farmhouses on one hilltop, a Main Villa, a Cottage and a one-bedroom Capanna annex…

Montalcino · 24 guests · 12 bedrooms
From €30,730 / week
Panoramic view
A 600 m² terrace raised above the countryside, with Montalcino straight ahead, the Val d'Orcia to the east and, on clear days…

Lucca & Garfagnana · 14 guests · 7 bedrooms
From €12,000 / week
Olive grove
Service: Fully staffed · Private chef

Castelfalfi · 6 guests · 3 bedrooms
From €84,000 / week
A private house with its own pool inside the medieval borgo, a combination that almost never comes up in a historic Tuscan…

Cortona · 18 guests · 9 bedrooms
From €10,150 / week
Private chapel · Frescoed interiors
A genuine 17th-century restoration: frescoed vaulted ceilings, painted walls and terracotta floors across more than 1,000 square…

Chianti · 19 guests · 10 bedrooms
From €59,500 / week
Heated pool · Working vineyard
Service: Private chef · Daily housekeeping · Spa

Lucca & Garfagnana · 15 guests · 8 bedrooms
From €15,000 / week
Frescoed interiors · Olive grove
Service: Private chef · Daily housekeeping

Castiglion del Bosco · 6 guests · 3 bedrooms
From €77,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Service: Daily housekeeping

Chianti · 18 guests · 9 bedrooms
From €17,400 / week
Working vineyard · Olive grove
Four private flats across two stone farmhouses on the Greve riverbank, each with its own kitchenette and living room…

Lucca & Garfagnana · 24 guests · 12 bedrooms
From €22,000 / week
Private chapel · Frescoed interiors
Service: Fully staffed · Private chef

Dimora Ghirlandaio · 37 guests · 20 bedrooms
From €91,000 / week
Heated pool · Private chapel
Service: Fully staffed · Private chef · Spa

Chianti · 18 guests · 9 bedrooms
From €20,300 / week
Infinity pool · Working vineyard
History on paper: a 1427 document from Bernardo di Bartolomeo Gherardi already describes this farm's forests, soil…

Lucca & Garfagnana · 8 guests · 4 bedrooms
From €7,500 / week
Olive grove
Service: Private chef · Daily housekeeping

Chianti · 26 guests · 13 bedrooms
From €67,900 / week
Working vineyard · Tennis court
Service: Private chef · Spa

Val d'Orcia · 26 guests · 13 bedrooms
From €22,344 / week
Infinity pool · Heated pool
Service: Spa

Lucca & Garfagnana · 14 guests · 6 bedrooms
From €19,000 / week
Panoramic view · Olive grove
Service: Private chef · Daily housekeeping

Castiglion del Bosco · 8 guests · 4 bedrooms
From €98,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Gym
Service: Daily housekeeping

Castelfalfi · 10 guests · 5 bedrooms
From €126,000 / week
Heated pool · Working vineyard
Service: Daily housekeeping

Castiglion del Bosco · 5 guests · 2 bedrooms
From €35,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Service: Daily housekeeping

Maremma · 18 guests · 9 bedrooms
Price on enquiry
Infinity pool · Heated pool
Service: Fully staffed · Private chef · Spa

Castelfalfi · 4 guests · 2 bedrooms
From €140,000 / week
Panoramic view · Step-free access
Service: Private chef

Castiglion del Bosco · 10 guests · 5 bedrooms
From €101,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Service: Daily housekeeping

Castiglion del Bosco · 6 guests · 3 bedrooms
From €84,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Service: Daily housekeeping

Castiglion del Bosco · 8 guests · 4 bedrooms
From €94,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Service: Daily housekeeping

Castiglion del Bosco · 6 guests · 3 bedrooms
From €63,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool
Service: Daily housekeeping
Some villas here publish rates and some do not — why we don’t publish prices for every villa explains the thinking, and what a villa in Tuscany costs gives the honest numbers. New to renting at this level? How renting works, and how to choose who you rent from. For the ranked, visited-in-person version: the 12 best luxury villas in Tuscany.
In Tuscany the word means four things in practice: the villa is staffed, the land is private, the kitchen can take a professional cook, and nothing is shared with another party. Anything short of that is a nice villa, which is a different and often perfectly good product.
Staffing is the clearest dividing line. A luxury villa arrives with a housekeeper most days and a gardener who keeps the pool, and it can take a private chef without the kitchen becoming a problem. A rental cottage gives you a key and a bin schedule. Both can have beautiful views; only one removes the work.
Privacy is the second. A great many Tuscan 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. The villas on this page are taken whole, and the land around them belongs to the villa for the week.
Each villa card above shows its current weekly from-rate, and the jump between levels buys three things: privacy, staff and position. Our guide to what a Tuscany villa costs has typical budgets.
At the entry level you get a genuinely private villa for eight to twelve, with a pool of its own and a housekeeper several days a week, usually around Lucca or in the Maremma, where land is less contested than in Chianti. One step up adds either the address or the staff: a Chianti or Val d'Orcia position with the view people picture, or a fuller service team. At the top you are renting an estate rather than a villa, typically with more than one building, more than one pool, and staff on site daily.
August is its own category. The same villa in the second week of August costs noticeably more than in late September, for weather most people find less comfortable. If the dates are movable, moving them is the single largest saving available.
The four regions are not interchangeable, and the difference matters more at this level than at any other. Chianti puts you within an hour of Florence and Siena and carries the highest land prices, so you pay for the position. The Val d'Orcia is the postcard, more remote, and better for a week that stays put than one that day-trips.
Lucca and the Garfagnana hold the historic ville lucchesi, villas built for entertaining with formal gardens and lemon villas, and it is the most practical base for families: Pisa airport is thirty minutes and the Versilia beaches forty. The Maremma is the only region that combines countryside with real coast, which makes it the answer whenever the party contains both people who want vineyards and people who want the sea.
Photographs are chosen to flatter and every agency has the same set. Four questions get past them, and any honest agent will answer all four without hesitation.
Ask for the pool dimensions, not a photograph. A 6x3 metre pool looks generous in a wide-angle shot and feels small at four in the afternoon with eight people in the villa. Ask what is genuinely private and what is shared, in plain terms, including the drive and the land. Ask exactly which staff are included and on which days, because "staffed" covers everything from a daily team to a cleaner on Fridays. And ask what the villa is like in bad weather, because a week with two wet days is normal and some villas have nowhere to put twelve people indoors.
We have stayed in or visited every villa on this page, and most are filmed. If a question about a specific villa cannot be answered from the page, ask us and the answer will be first-hand.
There are three sorts of company between you and a Tuscan villa. Marketplaces list tens of thousands of properties nobody at the company has seen, and take a fee from both sides. Brokers resell another agency's inventory, which is why the same villa appears on nine sites at nine slightly different rates. Then there are rental companies that contract directly with a small number of owners and know each villa personally. We are the third kind.
In practice that means a few dozen villas rather than thousands, and roughly one villa accepted for every twenty we visit. We are paid by the owners, so the rate quoted is the rate paid, and there is no booking fee added at checkout. The contract comes from the owner of the villa, not from a chain of intermediaries. Every property on this page has been visited in person, most are filmed, and the reason each one is in the collection is written at the top of its page.
The trade-off is honest: a marketplace will always show you more villas, and if the priority is the widest possible choice at the lowest possible price, one of them is the better tool. What a small rental company offers instead is that someone who has walked the property answers your enquiry, usually within twenty-four hours, and will tell you when a villa is wrong for your week.
Frequently asked