The long lunch at a wine estate
Chianti Classico or Brunello country: a tour of the cellars, then four courses under the pergola above the vines.
Central Italy
Tuscany Luxury Villa Rentals
Cypress-lined drives, a pool above the vines, and the long Tuscan lunch — in a villa we've walked, slept in, and chosen ourselves.
Tuscany is the Italy people mean when they close their eyes — the sculpted hills, the hill towns on their ridgelines, the wine that tastes like the view. It is also, for our money, the best place in the world to rent a villa. The region invented the form: noble families have been building country estates in these hills since the Renaissance, and the farmhouses, towers, and villas they left behind make the kind of vacation rental no hotel can imitate.
Every Tuscan villa in our collection is hand-selected and personally inspected — we know the owners, the housekeepers, and the road you'll take to dinner. Because we're a US-based, IATA-accredited agency, you book your villa in Tuscany with an American travel advisor in your own time zone, from first inquiry to the moment you're handed the keys.
Sub-regions
Explore by region
Each sub-region of Tuscany has its own character. Pick the one calling your name.
Best Villas
Best villas in Tuscany
Florence
Villa Elirenza
2 Beds·2 Baths·4 Guests
From €2,975 / week
Florence
Villa Florbianca
2 Beds·2 Baths·4 Guests
From €2,975 / week
Florence
Villa Nau
2 Beds·2 Baths·4 Guests
From €2,975 / week
Florence
Villa Rivarno
2 Beds·2 Baths·5 Guests
From €2,975 / week
Florence
Villa Turan
2 Beds·2 Baths·4 Guests
From €4,375 / week
Florence
Villa Arnova
3 Beds·3 Baths·5 Guests
From €4,375 / week
Chianti
Villa Benvista
3 Beds·3 Baths·6 Guests
From €15,300 / week
Florence
Villa Corte Nobile
3 Beds·3 Baths·6 Guests
From €3,675 / week
Florence
Villa Belcortese
4 Beds·4 Baths·8 Guests
From €4,375 / week
Lucca
Villa Frantoio
4 Beds·5 Baths·8 Guests
From €7,495 / week
Florence
Villa Scudo
4 Beds·4 Baths·8 Guests
From €4,375 / week
Chianti
La Novellina
5 Beds·6 Baths·10 Guests
From €7,060 / week
Chianti
Villa Danica
5 Beds·5 Baths·10 Guests
From €11,415 / week
Siena
Villa Hortus
5 Beds·5 Baths·10 Guests
From €12,000 / week
Florence
Villa Valorea
5 Beds·5 Baths·10 Guests
From €6,475 / week
Florence
Palazzo Sarzana-Fici
6 Beds·7 Baths·11 Guests
From €15,600 / week
Siena
Villa Aiola
6 Beds·5 Baths·12 Guests
From €12,145 / week
Chianti
Villa Fontanella
6 Beds·7 Baths·12 Guests
From €13,230 / week
Chianti
Villa Leonardo
6 Beds·6 Baths·12 Guests
From €6,855 / week
Chianti
Villa Morea
6 Beds·5 Baths·12 Guests
From €8,855 / week
Cortona
Villa Tullia
6 Beds·5 Baths·12 Guests
From €5,005 / week
Lucca
Casa Felice Matteucci
7 Beds·7.5 Baths·14 Guests
From €11,995 / week
Chianti
Villa Amarika
7 Beds·7 Baths·14 Guests
From €30,560 / week
Siena
Villa Araldica
7 Beds·7 Baths·12 Guests
From €14,450 / week
Chianti
Villa Colli
7 Beds·7 Baths·14 Guests
From €19,895 / week
Lucca
Villa Lenka
7 Beds·8 Baths·14 Guests
From €14,995 / week
Chianti
Villa Trionfante
7 Beds·6 Baths·14 Guests
From €28,570 / week
Chianti
Casa Bachicche
8 Beds·8 Baths·16 Guests
From €19,200 / week
Lucca
Casa Del Fattore
8 Beds·10 Baths·15 Guests
From €14,995 / week
Siena
Villa Cardinale
8 Beds·7 Baths·16 Guests
From €32,000 / week
Chianti
Villa Chiara
8 Beds·8 Baths·16 Guests
From €11,460 / week
Chianti
Villa Tavernaccia
8 Beds·7.5 Baths·16 Guests
From €32,000 / week
Cortona
Villa Ivana
9 Beds·12 Baths·18 Guests
From €9,450 / week
Siena
Villa Benessere
10 Beds·11 Baths·20 Guests
From €21,191 / week
Cortona
Villa Laura
10 Beds·10.5 Baths·20 Guests
From €25,000 / week
Chianti
Villa Montosca
10 Beds·10 Baths·20 Guests
From €15,000 / week
Lucca
Borgo Bernardini
12 Beds·12 Baths·24 Guests
From €23,200 / week
Chianti
La Poggiolaia
12 Beds·11 Baths·22 Guests
From €16,250 / week
Lucca
Villa Controni
12 Beds·14 Baths·24 Guests
From €21,995 / week
Siena
Villa Collina
20 Beds·20 Baths·36 Guests
Rates on request
Lucca
Coselli Estate
51 Beds·51 Baths·101 Guests
From €94,000 / week
Private experiences
Book a private experience
Expert-led private tours with Context Travel, priced per group, so the cost per person drops the more of you there are. Book direct, with no markup.
From$66 per person
Florence City Tour
A walking introduction to the historic center with a local historian — the Duomo, Piazza della Signoria, the Ponte Vecchio, and the small streets that connect them. The right way to start a week in Florence.
Private, priced per group: $349 for 2, about $66 per person for 12.
Book this experience
From$108 per person
Introduction to Siena Tour with the Duomo
A walk through medieval Siena with an art historian — the Duomo, the Campo, the Palazzo Pubblico, the contradas. Why this city stopped in the 14th century and was preserved by stopping.
Private, priced per group: $478 for 2, about $108 per person for 12.
Book this experience
From$77 per person
Introduction to Lucca Tour with Guinigi Tower
A walk inside the Renaissance walls with a local historian — the cathedral, the amphitheatre piazza built into the Roman ruin, the Guinigi Tower with the oak trees on top.
Private, priced per group: $415 for 2, about $77 per person for 12.
Book this experience
From$99 per person
Introduction to Pisa Tour with the Baptistery
The Campo dei Miracoli — the Tower, the Duomo, the Baptistery, the Camposanto — led by an art historian. Three hours, the right depth, then you go.
Private, priced per group: $544 for 2, about $99 per person for 12.
Book this experience
From$208 per person
Uffizi and Accademia Gallery Highlights Tour
Private tour: Uffizi and Accademia Gallery Highlights Tour. Led by Context Travel's local expert in Florence.
Private, priced per group: $865 for 2, about $208 per person for 8.
Book this experience
From$582 per person
Full-Day Tuscany Day Trip from Siena with Wine Tasting
Pienza, Montepulciano, the cypress road outside San Quirico, the abbey at Monte Oliveto Maggiore. The full Crete Senesi day with a local driver and a historian.
Private, priced per group: $2,572 for 2, about $582 per person for 6.
Book this experience
See all
Florence experiences
24 private tours
See all
Siena experiences
5 private tours
See all
Lucca experiences
1 private tour
See all
Pisa experiences
1 private tour
Disclosure: experiences are delivered by Context Travel. Bookings made through these links may earn Doorways a referral commission, at no additional cost to you. Doorways does not mark up Context Travel pricing.
Experiences
Activities & experiences
A private truffle hunt
Out with a hunter and his dog in the oak woods, then lunch where what you found goes straight onto the pasta.
Market morning, cooking afternoon
Shop a town market with a chef, then cook the Tuscan canon in your own villa kitchen: pici, panzanella, bistecca alla fiorentina.
Hill towns at golden hour
San Gimignano's towers, Volterra's alabaster, Pienza's pecorino, Montepulciano's cellars, each less than ninety minutes from most of our villas.
The Val d'Orcia drive
The most photographed valley in Italy: cypress ribbons, the village of Monticchiello, and the thermal pools at Bagno Vignoni.
Florence and Siena without the hotel
Day-trip to the Uffizi or the Campo, then come home to your own pool for the evening.
Travel Advisor
Let our specialists plan your trip
From the right villa to private chefs, boat charters, and bespoke experiences, we take care of every detail.
Beyond the Villa
Day trips
Florence
Forty-five minutes to an hour from most villas: the Uffizi, the climb up the Duomo, dinner in San Frediano, and home by midnight with a driver.
Siena
The Campo, the striped Duomo, and the Crete Senesi just below — an easy day from the Chianti and Siena hills.
San Gimignano & Volterra
The towers of San Gimignano in the morning, a saffron-pasta lunch, Volterra's alabaster workshops in the afternoon.
Val d'Orcia
The UNESCO valley of the postcards: pecorino at Pienza, Brunello at Montalcino, Vino Nobile at Montepulciano.
Lucca & Pisa
Cycle the walls of Lucca, then thirty minutes on to the Leaning Tower and the Campo dei Miracoli at Pisa.
The Versilia coast
Forte dei Marmi and the Tuscan beaches, about an hour from the Lucca hills for a day of sand and sea.
Climate
Average monthly highs
| January | February | March | April | May | June | July | August | September | October | November | December |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 49°F | 52°F | 58°F | 64°F | 71°F | 79°F | 85°F | 85°F | 78°F | 67°F | 56°F | 50°F |
Source: long-term monthly averages for the region. Sea temperatures stay comfortable for swimming May through October.
Where to Stay
Choosing your corner of Tuscany
Tuscany is the size of New Hampshire, and where you base yourself shapes the whole trip. These are the areas we know house by house.
Chianti is the classic. Vineyard villas between Florence and Siena, stone farmhouses above the Chianti Classico vines, wine estates at the end of white gravel roads. If it's your first Tuscan villa, start here.
Lucca is the walled city Puccini called home, ringed by some of the grandest historic villas in Italy, with the beaches of the Versilia coast twenty minutes west. The corner of Tuscany we know best of all.
Siena is medieval Tuscany. Villas in the sculpted clay of the Crete Senesi or the Chianti Senese vineyards, twenty minutes from the most beautiful piazza in Europe.
Cortona is Frances Mayes country: the hill town from Under the Tuscan Sun, and the home of Villa Laura, the actual estate where the film was shot, which we book.
Near Florence, the hills of Fiesole, the Mugello, and the first Chianti ridges put you in the countryside with the Uffizi thirty minutes away.
Where it is
Tuscany on the map
40 villas in Tuscany. Tap a pin to see the villa; locations are approximate. See all our villas on the map.
Travelers Ask
Frequently asked questions
Hand-selected villas in Tuscany generally start around €4,000–6,000 per week in high season for three- and four-bedroom houses with pools, €10,000–15,000 for larger estates sleeping ten to twelve, and €25,000+ for fully staffed properties for big groups. Spring and fall run 20–30% less than July and August. Every Doorways rate includes our travel advisor service, with no fee for working with us.
For a first trip, Chianti — central, classic, an hour from both Florence and Siena. For grand historic villas near a walkable city plus beaches, Lucca. For the medieval-landscape Tuscany of the photographs, Siena and the Val d'Orcia. For Under the Tuscan Sun country, Cortona. We'll talk it through with you, because matching travelers to the right corner of Tuscany is most of what we do.
Every villa in our collection does — it's one of our selection requirements. Many Tuscan rentals on the market rely on thick stone walls and shutters alone, which works until the hottest weeks of summer. We don't represent a villa unless it has proper air conditioning, so you never have to ask.
Yes. A villa vacation in Tuscany is a driving vacation: the roads are good, the distances are short, and the white-road drive to your own gate is part of the pleasure. We can arrange airport transfers and private drivers for your wine-tasting days.
For July and August, eight to twelve months ahead — the best villas in Tuscany are rebooked by returning guests before the season ends. For May, June, and September, four to six months. We sometimes have late availability, so it never hurts to ask.
May, June, and September. April brings wildflowers, October the grape harvest and the quiet after it. July and August are hot, busy, and wonderful anyway — that's pool-and-long-lunch season.
Both — it's what villas are for. We have family-friendly villas with fenced pools and room for the grandparents, and large-group estates that sleep sixteen or twenty, including Villa Laura of Under the Tuscan Sun.
Explore
Other destinations
Each region is hand-picked, walked, and slept in by us first. See which one is calling.
