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Tuscany Villas: 15 Real Villas, Area by Area

Villas

Tuscany Villas: 15 Real Villas, Area by Area

By Triplarks Editorial Checked

Quick picks not a ranking · only villas in this guide

Choose the area first. Chianti for both cities, Val d’Orcia for views, Lucca for families, the Maremma for beaches.

  1. Illustration of a villa in Lucca
    Illustration · see real photos on Booking.com

    Best for families

    VILLA GIOMA – Completely renovated country house

    Lucca hills · private pool

    Six bedrooms and an infinity pool, with Lucca and Pisa both an easy drive away.

    Check availability on Booking.com
  2. Illustration of a villa in Florence countryside
    Illustration · see real photos on Booking.com

    Best for couples

    Villa Il Paradisino

    Florence hills · seasonal pool

    A one-bedroom villa in a historic house, close enough to Florence for city days.

    Check availability on Booking.com
  3. Illustration of a villa in Val d'Orcia
    Illustration · see real photos on Booking.com

    Best pool view

    Villa Il Giardinello

    Val d'Orcia · infinity pool

    An infinity pool looking out over the Montalcino countryside.

    Check availability on Booking.com
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On this page
  1. Five villa areas
  2. Chianti: vineyards, with Florence and Siena both in reach
  3. See live prices for your dates
  4. Val d'Orcia: hill towns and the classic views
  5. Lucca & hills: a walled town within reach
  6. Maremma coast: the villa area with beaches
  7. Florence countryside: city days, quiet nights
  8. Villa or hotel?
  9. Before you book a villa
  10. When to book a Tuscany villa
  11. More on Tuscany
  12. Villas in Tuscany: FAQ

A Tuscan villa works best when the area fits the trip. Tuscany is bigger than it looks on a map, the drives between corners are long, and a villa in the wrong valley turns every day out into two hours in the car. This guide sorts villas by area first, so you choose where to wake up before you choose the pool. For each of the five areas below you will find what it suits, how far it is from Florence, and three real villas listed on Booking.com, with the bedrooms, guest numbers and pool details as the listing gives them. Where a listing does not state something, we leave it out rather than guess. We do not rank the villas and we do not quote prices, which change by the day; the map lets you see live prices for your own dates. If you are still deciding between a villa and a hotel, or how to split your days, the Tuscany itinerary helps with the route.

Some links below are affiliate links. We may earn a commission if you book through them, at no extra cost to you. We do not rank hotels, and any prices on the map come live from the booking sites.

Step 1 · Pick the area

Five villa areas

Schematic map of Tuscany with five villa areas51234FlorenceSienaLucca
Schematic · not to scale
  1. 1Chianti

    Wine and a first trip · car needed · about 45 min to Florence

    See 3 villas ↓Villas around Radda in Chianti →
  2. 2Val d'Orcia

    Hill towns and views · car needed · about 1 hr 45 min to Florence

    See 3 villas ↓Villas in Val d'Orcia →
  3. 3Lucca & hills

    Families, a town nearby · car helps · about 1 hr 15 min to Florence

    See 3 villas ↓Villas near Lucca →
  4. 4Maremma coast

    Beach days · car needed · about 2 hrs to Florence

    See 3 villas ↓Villas in the Maremma →
  5. 5Florence countryside

    City days, quiet nights · car helps · 20–40 min to Florence

    See 3 villas ↓Villas near Florence →
Illustration of Chianti
Illustration · Chianti

Area 1 of 5

Chianti: vineyards, with Florence and Siena both in reach

Good for wine and a first tripCar neededAbout 45 min to Florence

Chianti is the stretch of hills between Florence and Siena, and it is the easiest area to pick if this is your first villa holiday in Tuscany. Vineyards and olive groves cover the slopes, woods fill the valleys, and small towns such as Greve and Panzano sit along the SR222, the old Chiantigiana road, with Radda and Gaiole a short drive off it. From most villas here you can reach Florence or Siena in under an hour, so one villa covers both cities without packing up. The catch is the driving: the roads are narrow and winding, and the last stretch to many farmhouses is a gravel track, so twenty kilometres can take forty minutes. Evenings are quiet, and most villages have a wine shop, a butcher and a trattoria or two. Expect more villas here than in any other area, and more competition for them in June and September, when the weather is warm and the vineyards are at their best.

Live prices

See live prices for your dates

Prices appear on the pins once dates are set. We pre-fill a week about a month ahead; change the dates on the map to see yours.

Check Tuscany villas on Booking.comCompare on Agoda
Illustration of Val d'Orcia
Illustration · Val d'Orcia

Area 2 of 5

Val d'Orcia: hill towns and the classic views

Good for scenery and slow daysCar neededAbout 1 hr 45 min to Florence

Val d’Orcia is the Tuscany of postcards: open, rolling farmland, lines of cypress trees on the ridges and hill towns such as Pienza, Montalcino and San Quirico d’Orcia. The whole valley is a UNESCO World Heritage site, and it looks its best in spring, when the wheat is green, and in late summer, when it turns gold. Villas here tend to be restored farmhouses, or poderi, set on their own hill with a pool facing the view. It is further from Florence than Chianti, so treat the city as one long day out rather than a regular trip. In return you get Montalcino and Montepulciano wine estates, the hot springs at Bagno Vignoni and Bagni San Filippo, and very dark, quiet nights. Shops and restaurants are in the hill towns, so plan a drive for every meal you do not cook yourself.

Illustration of Lucca & hills
Illustration · Lucca & hills

Area 3 of 5

Lucca & hills: a walled town within reach

Good for familiesCar helpsAbout 1 hr 15 min to Florence

Lucca is a calm, flat city inside complete Renaissance walls, and the top of those walls is a tree-lined path you can walk or cycle all the way round. The hills to the north and south are greener and wetter than central Tuscany, with chestnut woods, olive groves and old patrician villas. For families this is the most practical area: the town is close for gelato, bikes and an evening walk, Pisa airport is near, and the beaches of the Versilia coast are within a short drive for a day by the sea. Villas range from big country houses with pools in the hills to family homes on the edge of town, where you can leave the car and walk in. Florence is a straightforward train ride from Lucca station, which is useful if you would rather not drive into the city.

Illustration of Maremma coast
Illustration · Maremma coast

Area 4 of 5

Maremma coast: the villa area with beaches

Good for beach daysCar neededAbout 2 hrs to Florence

The Maremma is southern Tuscany’s coast and its hinterland: long sandy beaches backed by umbrella pines, the Parco della Maremma nature reserve, and inland hill towns such as Scansano, Capalbio and Pitigliano. It feels further from the art cities than the rest of Tuscany, and for many people that is the point. Choose it if beach days matter as much as the pool. Monte Argentario, a rocky promontory joined to the mainland by sand bars, has clear water and small coves, while the hills around Scansano are Morellino wine country with views down to the sea. The thermal pools at Saturnia are a short drive inland. Villas here are often smaller farmhouses or agriturismi rather than grand houses, and distances are long, so a car is essential.

Illustration of Florence countryside
Illustration · Florence countryside

Area 5 of 5

Florence countryside: city days, quiet nights

Good for sightseeingCar helps20–40 min to Florence

The hills that ring Florence, from Fiesole and Sesto Fiorentino in the north to Bagno a Ripoli and Impruneta in the south, are the answer if the Uffizi and the Duomo are the main reason for the trip. You sleep among olive groves and come down to the city by car, bus or a short taxi ride, then escape the summer crowds in the evening. Several of the villas here are historic houses with formal gardens, and some are on estates that also run a restaurant or let rooms. The trade-off is that this is not deep countryside: you will hear the occasional road, and the views are of the city plain rather than empty hills. Do not plan to drive into the centre itself, which is a limited traffic zone (ZTL) with cameras and fines; park at the edge or use public transport. Southern Chianti is close enough for a day among the vineyards.

Villa or hotel?

A villa is not automatically the better choice in Tuscany. It is a different kind of trip: you stay put, cook some of your own meals, and drive out to the towns. A hotel or B&B suits a route that moves every two or three nights. Here is the honest split.

A villa makes sense if

  • You stay a week in one place, which is also how many villas prefer to be booked
  • You are a group or a family sharing the cost, the kitchen and the pool
  • You plan to drive out each day and come back to the same view
  • You have young children who need a garden and a set bedtime more than a hotel bar

A hotel makes more sense if

  • You move every two or three nights
  • You do not want to drive, or to drive back on country roads after dinner
  • You want breakfast, daily cleaning and someone at a desk to ask
  • You are a couple on a short trip, when a whole house is more than you need
Where to stay in Tuscany: hotels by area →

There is a middle way too. An agriturismo is a working farm that lets apartments or rooms, often with a shared pool and sometimes with dinner on offer. Several places in this guide are on estates like that, which is why the cards say whether a pool is private, shared or simply on site. If you are torn, a week in a villa in one area followed by two nights in a Florence hotel works well for most first trips; our Florence neighbourhood guide covers the city half.

Before you book a villa

Villa listings vary far more than hotel rooms, and the details that spoil a holiday are usually in the small print. Read these eight things on the listing itself, because terms are set by each owner.

  1. Minimum stayMany villas only take bookings of a set number of nights, often a week in July and August.
  2. Changeover daySome only allow arrivals on one day of the week, typically Saturday, which fixes your flights.
  3. Pool seasonCheck the dates the pool is open, and whether it is private, shared with other guests or heated.
  4. Air conditioningCheck which rooms have it, not only whether it is listed. Stone houses stay cool by day but bedrooms can be warm at night in July.
  5. Do you need a car?Check the distance to the nearest shop and restaurant, and whether the host suggests a car at all.
  6. Security depositCheck the amount, how it is taken and when it is returned.
  7. Cleaning and extra feesCheck what is added at checkout or paid on arrival, such as final cleaning, linen, heating or the local tourist tax.
  8. Access roadCheck whether the last stretch is a gravel or unpaved road, and how steep it is, especially with a low hire car.

When to book a Tuscany villa

Late May, June and September are the sweet spot: warm enough for the pool, green or golden hills, and towns that are busy but not packed. July and August are the hottest and most expensive weeks, when Italians are on holiday too, and the best large villas are often booked many months ahead. In April and October the countryside is lovely and quieter, but many pools are not yet open or have already closed, and evenings are cool enough for the fireplace. Winter villa stays work for slow food-and-wine trips if the house has proper heating. For the weather month by month, see the best time to visit Italy. To check prices for your own dates, use the map above or open any villa on Booking.com; we do not show prices here because they change daily.

Planning on Pinterest?

Save the five areas for later

This card is the whole guide in one image: five areas and what each one suits. Save it now and come back to the villas when your dates are fixed.

Save to Pinterest

More on Tuscany

Villas in Tuscany: FAQ

Do you need a car for a villa in Tuscany?

In most rural areas, yes. Villas are usually outside the towns, buses between villages are infrequent, and the last stretch is often a gravel road. The hills around Lucca and Florence are the easiest to manage with less driving, because both cities have train stations.

Which area is best for a first villa stay?

Chianti, if you want both Florence and Siena within a day trip. Choose Val d'Orcia for scenery and quiet, the Lucca hills for families, or the Maremma coast if beach days matter most.

Are Tuscany villas with a private pool easy to find?

Yes in Chianti, Val d'Orcia and the Lucca hills, where many farmhouses have their own pool. On the Maremma coast and near Florence, more places share a pool with other houses on the same estate, so check the wording on the listing.

When are villa pools open?

It depends on the owner. Many open from late April or May to late September or early October. Pool dates are usually given on the listing; check them before you book an early-spring or late-autumn stay.

Can I book a villa for only three nights?

Sometimes. Many villas set a minimum stay and a fixed changeover day in summer, so short stays are easier outside July and August, or in a hotel or agriturismo.

How far ahead should I book a Tuscany villa?

For July and August, and for large villas that sleep ten or more, book as early as you can, often the winter before. For May, June and September a few months ahead usually leaves a good choice.

Keep planning Italy

Written and checked by

Triplarks Editorial

An editorial desk, not an invented persona: research, drafting and fact-checking are done by the same small team. Every number here carries the date it was read.

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