Central Italy
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.
Where to Stay
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.
Sub-regions
Each sub-region of Tuscany has its own character. Pick the one calling your name.
Best Villas
Chianti
3 Beds·3 Baths·6 Guests
From €15,300 / week
Lucca
4 Beds·5 Baths·8 Guests
From €7,495 / week
Chianti
5 Beds·6 Baths·10 Guests
From €7,060 / week
Chianti
5 Beds·5 Baths·10 Guests
From €11,415 / week
Siena
5 Beds·5 Baths·10 Guests
From €12,000 / week
Siena
6 Beds·5 Baths·12 Guests
From €12,145 / week
Chianti
6 Beds·7 Baths·12 Guests
From €13,230 / week
Chianti
6 Beds·5 Baths·12 Guests
From €8,855 / week
Cortona
6 Beds·5 Baths·12 Guests
From €5,005 / week
Lucca
7 Beds·7.5 Baths·14 Guests
From €11,995 / week
Chianti
7 Beds·7 Baths·14 Guests
From €30,560 / week
Siena
7 Beds·7 Baths·12 Guests
From €14,450 / week
Chianti
7 Beds·7 Baths·14 Guests
From €19,895 / week
Chianti
7 Beds·6 Baths·14 Guests
From €28,570 / week
Lucca
8 Beds·10 Baths·15 Guests
From €14,995 / week
Siena
8 Beds·7 Baths·16 Guests
From €32,000 / week
Chianti
8 Beds·8 Baths·16 Guests
From €11,460 / week
Lucca
8 Beds·8 Baths·16 Guests
From €14,995 / week
Chianti
8 Beds·7.5 Baths·16 Guests
From €32,000 / week
Cortona
9 Beds·12 Baths·18 Guests
From €9,450 / week
Siena
10 Beds·11 Baths·20 Guests
From €25,000 / week
Cortona
10 Beds·10.5 Baths·20 Guests
From €19,000 / week
Chianti
10 Beds·10 Baths·20 Guests
From €15,000 / week
Lucca
12 Beds·12 Baths·24 Guests
From €23,200 / week
Chianti
12 Beds·11 Baths·22 Guests
Rates on request
Lucca
12 Beds·14 Baths·24 Guests
From €21,995 / week
Siena
20 Beds·20 Baths·36 Guests
Rates on request
Lucca
51 Beds·51 Baths·101 Guests
From €94,000 / week
Experiences
Chianti Classico or Brunello country: a tour of the cellars, then four courses under the pergola above the vines.
Out with a hunter and his dog in the oak woods, then lunch where what you found goes straight onto the pasta.
Shop a town market with a chef, then cook the Tuscan canon in your own villa kitchen: pici, panzanella, bistecca alla fiorentina.
San Gimignano's towers, Volterra's alabaster, Pienza's pecorino, Montepulciano's cellars, each less than ninety minutes from most of our villas.
The most photographed valley in Italy: cypress ribbons, the village of Monticchiello, and the thermal pools at Bagno Vignoni.
Day-trip to the Uffizi or the Campo, then come home to your own pool for the evening.
Travel Advisor
From the right villa to private chefs, boat charters, and bespoke experiences, we take care of every detail.
Beyond the Villa
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.
The Campo, the striped Duomo, and the Crete Senesi just below — an easy day from the Chianti and Siena hills.
The towers of San Gimignano in the morning, a saffron-pasta lunch, Volterra's alabaster workshops in the afternoon.
The UNESCO valley of the postcards: pecorino at Pienza, Brunello at Montalcino, Vino Nobile at Montepulciano.
Cycle the walls of Lucca, then thirty minutes on to the Leaning Tower and the Campo dei Miracoli at Pisa.
Forte dei Marmi and the Tuscan beaches, about an hour from the Lucca hills for a day of sand and sea.
Climate
| 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 it is
Travelers Ask
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
Each region is hand-picked, walked, and slept in by us first. See which one is calling.
“A fabulous experience in every way. Thank you for all your help in working with us to choose the perfect villa and for all the recommendations. A trip to remember.”Doorways Client · Villa Larianella
“Our experience with Doorways was exceptional — La Casetta and The Farmhouse were impeccable, and the owners’ hospitality was off the charts. Two of the most magical properties in all of Umbria. Can’t wait to return!”Doorways Client · Sogno Casetta & Farmhouse
“My longtime dream of renting a villa with friends in Tuscany became a reality thanks to Susan and Doorways. Villa Laura was the perfect property — and Susan is trustworthy, professional, and passionate about her stunning properties.”Doorways Client · Villa Laura
“Awesome! Great central location and splendid views. A great, great place. This was my second time with Doorways and it was even better than the first!”Doorways Client · Poggio delle Rose
“We absolutely loved the villa on Lake Como. The local concierge devised a fabulous itinerary, and each of the services — provisions, chefs, tours on the lake — was exceptional. Our first time renting a villa, and we would highly recommend.”Doorways Client · Lake Como
“Phenomenal. The villa was a restful, beautiful place to stay, with spectacular views in Tuscany. Fresh herbs outside the door, a wood fire, more amazing views, and a quick dip in the pool. The four of us loved it — go, enjoy!”Doorways Client · Tuscany
“We couldn't have been better-taken care of! This was a very special experience — one that will be etched in our hearts forever.”Doorways Client · Villa Plaisir
“Three-sixty views over golden wheat fields and sunflower crops, a beautifully kept pool, an olive grove and fruit trees. And Mariela the housekeeper — what a wonderful person. The grounds, the views and the pool: magnificent.”Doorways Client · Villa Molinazzo
“I cannot speak highly enough of Doorways! Susan planned our stay and our wedding at Villa Laura in Cortona, and it was beyond our wildest dreams. Sophie the house manager gave us the best week of all our lives.”Doorways Client · Villa Laura · Wedding
“From arrival to departure, the week was filled with incredible hospitality, warmth and beauty. The description and photos did not do the experience justice. Xenia has created something truly special, and the Chianti hills were idyllic. Belissimo!”Doorways Client · Il Casolare
“Villa Mida is a delightful surprise — amazing water views, a unique indoor spa, attentive staff. After full days exploring the Amalfi Coast it was wonderful to return to a soothing setting to recharge. We can’t wait to return!”Doorways Client · Villa Mida
“This villa was amazing — everywhere you looked was a “wow” moment. Pool, hot tub, outdoor kitchen, king-size beds with double shower heads. Bocce, foosball, ping pong. Thanks Susan for recommending this property for the four couples.”Doorways Client · A Tuscan Villa
“The villa was spectacular. The service from the property manager and maid was first class, and the modern amenities were much appreciated. A five-star luxury experience.”Doorways Client · Villa Brezzablu
“10/10 would highly recommend. Susan is the utmost professional, full of knowledge, and she really gets to know you. Her trip planning and the details she provides are very valuable. A must if you want a unique and tailored experience!”Doorways Client · Doorways Client
“We had the absolute best experience working with Susan. We stayed at CasaCau in Roma — wonderful accommodations, delicious breakfast every morning, and the location was absolutely amazing — just down the road from the Fontana di Trevi. A real gem!”Doorways Client · CasaCau
“La Poggiolaia is a beautiful property with an amazing pool — and the sunsets are stunning.”Doorways Client · La Poggiolaia
“Comfortable in every way — and the chef was outstanding. Walking, eating, exploring… just entering into the beauty and culture of Italy.”Doorways Client · Casa del Fattore
