Italy · Hill towns, vineyards and stone farmhouses
Villas in Tuscany
Tuscany is where many people first imagine a villa holiday, and it rarely disappoints. Stone farmhouses sit on hilltops above vineyards. Cypress trees line the drive. Evenings end on a terrace with a view that has barely changed in centuries.
Villa life
Why a villa in Tuscany
The region is larger and more varied than it first seems. Chianti is different from the Val d'Orcia, which is different again from the hills around Lucca or the Maremma coast. Where you stay shapes the whole trip, so we start by understanding what you want your days to look like.
Rural Tuscany is built for villa life. Many of the best places to stay are restored farmhouses, known as casali or poderi, and historic estates that were never hotels. Space is generous, pools are common and the countryside is the point.
A villa also suits the pace of the region. Long lunches, market mornings, wine tastings and a late swim are easier when home is a house rather than a hotel room. For groups and families, it means everyone can be together without being on top of one another.
Especially good for
- Families and multi-generational groups
- Large gatherings and milestone celebrations
- Food and wine lovers
- Couples wanting quiet countryside
- Weddings and vow renewals at approved estates
Where to stay
The best areas for a villa in Tuscany
- 01
Chianti
The classic Tuscan landscape between Florence and Siena. Vineyards, wooded hills and villages like Greve, Radda, Castellina and Panzano. Well placed for day trips to both cities.
- 02
Val d'Orcia
A UNESCO-listed valley south of Siena with sweeping views, and the towns of Pienza, Montalcino and San Quirico d'Orcia. Quieter, more open and wonderfully photogenic.
- 03
Montepulciano and Cortona
Hilltop towns on the eastern side of the region, close to Umbria. Good for travelers who want to walk into a town for dinner.
- 04
Lucca and the northern hills
Green hills and grand old villas around the walled city of Lucca. Convenient for Pisa airport and within reach of the coast.
- 05
The Maremma and coast
Southern Tuscany, where the countryside meets the sea. Beaches, Monte Argentario and a wilder, less-visited feel.
- 06
Around Siena
Villas within a short drive of one of Italy's finest medieval cities, and the pale, rolling Crete Senesi to the south.
What you can request
Villa types in Tuscany
- Restored farmhouses
- Stone casali with terracotta floors, beamed ceilings and a pool in the olive grove.
- Wine estates
- Villas on working vineyards, sometimes with tastings and cellar visits.
- Historic villas
- Grand country houses with formal gardens, often suited to larger groups.
- Hamlets and borghi
- Several houses on one property, ideal when families want their own space.
We don’t publish villa listings, because availability changes constantly. Tell us your dates and we’ll send you villas that are available, with full photos and details.
Days out
Typical experiences
- Wine tastings in Chianti, Montalcino and Montepulciano
- Day trips to Florence, Siena, Pisa and Lucca
- Cooking classes and a private chef night at the villa
- Truffle hunting in season
- Cycling and walking through the Val d'Orcia
- Thermal springs at Bagno Vignoni and Saturnia
Seasons
When to visit Tuscany
- April to June
- Green hills, wildflowers and comfortable temperatures. May and June are among the best months for a villa stay.
- July and August
- Hot, lively and the peak for families. Pools become essential. Book early for the best villas.
- September and October
- Harvest season, warm days and cooler nights. Excellent for food and wine trips.
- November to March
- Quiet and atmospheric, with olive oil pressing in late autumn. Fewer villas are available, and pools are usually closed.
Practical notes
Getting there, groups and local tips
Getting there
- Florence (FLR) and Pisa (PSA) are the main airports. Rome (FCO) works well for southern Tuscany and the Maremma.
- High-speed trains connect Florence to Rome and Milan, but a car or driver is essential for rural villas.
- Many villas are reached by white gravel roads. Worth knowing if you're renting a car.
For groups
- Tuscany has a good supply of larger villas and estates, but the best book early for summer.
- Estates with separate houses work well for families who want privacy.
- Consider how far you'll be from a town if not everyone wants to drive to dinner.
Local tips
- Summer rentals often run Saturday to Saturday. Some villas are more flexible outside peak season.
- Restaurants in small towns fill quickly on weekends. The villa's local contacts can help.
- Many towns restrict driving in historic centers (ZTL zones). Park outside and walk in.
- The Palio di Siena takes place on July 2 and August 16. Wonderful to see, busy around the city.
Villa collections
Popular requests in Tuscany
- Explore
Villas with Pools
The private pool, and everything around it.
- Explore
Villas for Large Groups
Room for everyone, and a table big enough.
- Explore
Family Villas
Space for children, and for the adults too.
- Explore
Wedding Villas
Villas where celebrations are genuinely welcome.
- Explore
Staffed Villas
A villa that looks after you while you're there.
Questions
Tuscany villa FAQs
What's the best part of Tuscany to rent a villa?
It depends on the trip. Chianti is ideal if you want easy access to Florence and Siena. The Val d'Orcia suits travelers after views and quiet. Lucca is convenient for Pisa airport, and the Maremma adds beaches. Tell us what matters and we'll suggest areas as well as villas.
Do Tuscan villas usually have pools?
Most rural villas do. Pool size, heating and privacy vary, so we'll check those details for your dates.
Do we need a car when staying in a Tuscan villa?
Usually, yes. Most villas are in the countryside. If you'd prefer not to drive, we can look for villas within walking distance of a town, or ask about drivers.
How far ahead should we book a villa in Tuscany?
For July and August, and for larger villas, the earlier the better. Many good villas are booked well ahead of the summer. Shoulder seasons are more flexible.
From the Journal
Reading for your Tuscany trip
Destinations 7 min read
The Best Villa Destinations in Italy
Six regions, six very different trips. How to choose the right part of Italy for your villa.
Destinations 6 min read
Tuscany vs. the Amalfi Coast: Which Is Right for Your Villa Trip?
Two of Italy's most-loved regions, and two completely different villa holidays.
Planning 5 min read
Villa vs. Hotel for a Group Trip
When a villa works better than a hotel for a group, and the few times it doesn't.
Plan your trip
Tell us about your Tuscany trip.
Where in Tuscany, when, who's coming, and what matters most. We'll search across our villa partners and send you options that fit.
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