# Chianti Villas 2027: Luxury Villa Rentals | Doorways > Luxury villas in the Chianti hills between Florence and Siena: vineyard estates, farmhouse pools and the SS222 wine road from your door. Source: https://villavacations.com/destinations/chianti/ ![Chianti villas — hand-selected luxury rentals](https://villavacations.com/wp-content/uploads/2026/06/chianti-hero-amarika.jpg) Classic Tuscany # Chianti Luxury Villa Rentals Cypress-lined drives, family vineyards at golden hour, and a glass of Sangiovese with the hills going pink. The Chianti hills between Florence and Siena are the Tuscany of the postcards — for good reason. Cypress-lined gravel roads, stone farmhouses behind iron gates, and family vineyards that have been making wine for ten generations. Stay in a villa here and the day finds its own rhythm. Morning coffee under a pergola, a long lunch at the winery you can see from your bedroom window, a swim in your own pool, dinner driven down to Greve or Panzano or eaten at the kitchen table with what your chef bought at the market that morning. Want a base nearer the historic city? Our [villas near Siena](https://villavacations.com/destinations/siena/) are forty-five minutes south. Villas Hand-selected stays in Chianti [Browse Villas →](https://villavacations.com/villas/?region=Chianti) Best Villas ## Best villas in *Chianti* ![Villa Benvista](https://villavacations.com/wp-content/uploads/2026/06/Villa-Benvista-hero-1024x682.webp) Chianti ### Villa Benvista 3 Beds·3 Baths·6 Guests From €15,300 / week ![La Novellina](https://villavacations.com/wp-content/uploads/2026/06/La-Novellina-hero.webp) Chianti ### La Novellina 5 Beds·6 Baths·10 Guests From €7,060 / week ![Villa Danica](https://villavacations.com/wp-content/uploads/2026/06/Villa-Danica-hero-1024x683.webp) Chianti ### Villa Danica 5 Beds·5 Baths·10 Guests From €11,415 / week ![Villa Fontanella](https://villavacations.com/wp-content/uploads/2026/06/Villa-Fontanella-hero-1024x640.webp) Chianti ### Villa Fontanella 6 Beds·7 Baths·12 Guests From €13,230 / week ![Villa Leonardo](https://villavacations.com/wp-content/uploads/2026/10/20181227_125401jpg-1024x682.jpg) Chianti ### Villa Leonardo 6 Beds·6 Baths·12 Guests From €6,855 / week ![Villa Morea](https://villavacations.com/wp-content/uploads/2026/06/Villa-Morea-hero-1024x683.webp) Chianti ### Villa Morea 6 Beds·5 Baths·12 Guests From €8,855 / week ![Villa Amarika](https://villavacations.com/wp-content/uploads/2026/06/Villa-Amarika-hero-1024x682.webp) Chianti ### Villa Amarika 7 Beds·7 Baths·14 Guests From €30,560 / week Chianti ### Villa Colli 7 Beds·7 Baths·14 Guests From €19,895 / 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 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 Chianti ### Villa Montosca 10 Beds·10 Baths·20 Guests From €15,000 / week Chianti ### La Poggiolaia 12 Beds·11 Baths·22 Guests From €16,250 / week [View All Villas in Chianti](https://villavacations.com/villas/?region=Chianti) 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 $582 per person Full day · private · tastings included ### 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 From $1,696 per group Half day · private · tastings included ### Chianti Excursion with Wine Tasting from Florence Private tour: Chianti Excursion with Wine Tasting from Florence. Led by Context Travel's local expert in Florence. Book this experience From $543 per person Full day · private ### Full-Day San Gimignano and Volterra Day Trip from Siena San Gimignano's towers, Volterra's Etruscan museum and alabaster workshops. The medieval-Etruscan double bill of the Tuscan hills west of Siena. Private, priced per group: $2,494 for 2, about $543 per person for 6. Book this experience From $2,718 per group Full day · private · tastings included ### Full-Day Tuscany Day Trip from Florence with Wine Tasting Private tour: Full-Day Tuscany Day Trip from Florence with Wine Tasting. Led by Context Travel's local expert in Florence. Book this experience From $376 per person Half day · private · tastings included ### Chianti Excursion with Wine Tasting from Siena Two cantinas in Chianti Classico, a long lunch between them, the SP408 road through the cypresses. A working-vineyard day, with a sommelier driver. Private, priced per group: $1,764 for 2, about $376 per person for 6. Book this experience From $1,557 per group Half day · private · tastings included ### Half-Day Tuscany Carmignano Wine Tasting Tour from Florence Private tour: Half-Day Tuscany Carmignano Wine Tasting Tour from Florence. Led by Context Travel's local expert in Florence. Book this experience [See all Siena experiences 5 private tours](https://villavacations.com/experiences/siena/) [See all Florence experiences 24 private tours](https://villavacations.com/experiences/florence/) Disclosure: experiences are delivered by [Context Travel](https://www.contexttravel.com/?ref=Doorways_Villa_Vacations). 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* ### Private vineyard tour and tasting A morning at a small Chianti Classico producer — Castello di Ama, Felsina, Fontodi, or a family estate without a sign on the road. Cellar tour, four wines, and lunch with the winemaker. ### Cooking class at a Chianti farmhouse A nonna and a long wooden table. Fresh pici, ribollita, tiramisu, and a bottle of the house red. Half a day, ending with the meal you made. ### Truffle hunt with dogs An hour east toward Casentino with a truffaio and his Lagotto Romagnolo. Two hours of slow walking in the woods, then truffle pasta for lunch at the farm. ### Drive the Strada Chiantigiana (SR222) The two-lane road from Florence to Siena that threads through every postcard view of Chianti. Sixty kilometres, half a day if you stop for lunch, a whole day if you stop for tastings. ### Olive harvest at a family frantoio Late October and early November. Pick olives in the morning, watch them go into the press in the afternoon, taste the green-gold oil within hours of pressing. ### A morning at the Greve market Saturday and Tuesday mornings in Piazza Matteotti. Cheeses, cured meats, fresh ricotta, vegetables from the surrounding farms — the building block of every great Tuscan dinner. 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. [Email a travel advisor](https://villavacations.com/contact-us/) [Call 1 (800) 409-4346](tel:+18004094346) Beyond the Villa ## Day *trips* ### Florence Forty-five minutes north. The Duomo, the Uffizi, dinner in San Frediano, and back to the villa by midnight. Tickets booked ahead, our driver waits. ### Siena Forty-five minutes south. The Campo, the Duomo, an hour in the Sant'Antimo or Crete Senesi just below, lunch at a trattoria your concierge knows. ### San Gimignano & Volterra The towers of San Gimignano in the morning, a saffron-pasta lunch, then Volterra's Etruscan walls and alabaster workshops in the afternoon. ### Arezzo & Cortona An hour east. The Piero della Francesca frescoes in San Francesco, then dinner with Frances Mayes country views from Cortona's medieval centre. ### Val d'Orcia & Montepulciano Ninety minutes south to the most photographed valley in Italy. Pienza for pecorino, Montalcino for Brunello, Montepulciano for Vino Nobile. ### Pisa & Lucca A full day west. The Leaning Tower at dawn before the crowds, then Lucca for a bicycle ride around the walls and dinner in the centro storico. Climate ## Average *monthly highs* | January | February | March | April | May | June | July | August | September | October | November | December | | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | | 50°F | 53°F | 59°F | 65°F | 73°F | 81°F | 86°F | 86°F | 78°F | 67°F | 56°F | 51°F | Source: long-term monthly averages for the region. Sea temperatures stay comfortable for swimming May through October. Where it is ## Chianti on the *map* 13 villas in Chianti. Tap a pin to see the villa; locations are approximate. [See all our villas on the map](https://villavacations.com/villa-map/). Travelers Ask ## Frequently asked *questions* Chianti is wine country, but that's only half of it. The region between Florence and Siena — the Chianti Classico zone, marked by the black-rooster Gallo Nero — is one of the most beautiful agricultural landscapes in Europe: cypresses, olive groves, oak woods, and roughly a thousand small wineries, most of them family-run. The towns are tiny and unhurried. Greve in Chianti is the unofficial capital, with its weekend market in the triangular piazza. Castellina, Radda, and Gaiole are even smaller — stone villages on hilltops, with a single trattoria, a single enoteca, a single butcher (Antica Macelleria Cecchini in Panzano, the most famous in Italy). Volpaia is a medieval hamlet inside a working winery. The food is essentially the food the contadini ate two hundred years ago, only better-sourced now: bistecca alla fiorentina, pici cacio e pepe, ribollita, pappa al pomodoro, pecorino di [Pienza](https://villavacations.com/destinations/siena/) with chestnut honey. Lunch at a vineyard is the meal of the trip, every trip. And the wine — Sangiovese-based, big, structured, made for food. The classic stops are Antinori in the Bargino visitor centre, Castello di Brolio (where the Chianti formula was invented in 1872), Castello di Ama for the modern style, Felsina, Fontodi, Querciabella. Our concierge books tastings at the producers that don't take walk-ins. For Chianti we love May, June, and September — long warm days, settled weather, and the vineyards either in flower or full of fruit. July and August are stunning but hot (highs in the mid-to-upper 80s°F); August also coincides with Italian holidays so the smaller producers close. Late September through mid-October is the vendemmia — the wine harvest — and arguably the most beautiful time in Chianti: cool mornings, warm afternoons, vineyards turning gold, festivals in every village. Chianti has a classic inland Mediterranean climate: hot dry summers and cool wet winters. Average monthly highs range from around 50°F in January to 86°F in July and August. May through September is reliably warm and sunny; pool weather is mid-May through late September. Spring and autumn are mild but can carry rain. Winter is grey, quiet, and a beautiful time if you want a fire in the villa. Bistecca alla fiorentina (a three-finger-thick Chianina T-bone, served rare with olive oil), pici cacio e pepe, ribollita, pappa al pomodoro, fresh pecorino with chestnut honey, panzanella in summer, wild boar ragù in autumn. The famous addresses: Officina della Bistecca and Solociccia in Panzano (both Dario Cecchini), Osteria di Passignano at Antinori, Locanda di Pietracupa above Greve, La Bottega in Volpaia. Our concierge books any of them. For a first visit: Antinori Bargino (the modern flagship), Castello di Brolio (history), Castello di Ama (modern art + wine), Felsina, Fontodi, Querciabella, Castello di Volpaia. For smaller family estates without signage we can arrange private visits — that's where Chianti is most itself. Cooking classes with a nonna, truffle hunts with dogs, olive-oil tastings at the frantoio, market mornings in Greve or Panzano, cycling the hills (e-bikes are easy here), antique markets in nearby Arezzo (first Sunday of every month), and the Anghiari and Lucignano hilltop villages most travellers never reach. Florence (45 minutes north), Siena (45 minutes south), San Gimignano and Volterra (one hour west), Arezzo and Cortona (one hour east), and the Val d'Orcia — Pienza, Montalcino, Montepulciano — about ninety minutes south. Yes. Public transport in Chianti is essentially nonexistent — the small villages and the wineries that make Chianti worth the trip are all reached by car or by private driver. We arrange driver service for full days (vineyard tours, dinner out) and we recommend a small rental car for the villa stay itself so you can explore on your own. Our Chianti villas run from about €7,000 a week for a five-bedroom farmhouse like La Novellina to about €32,000 a week for an eight-bedroom estate like Villa Tavernaccia. For couples, the cottages at La Poggiolaia start at €1,050 a week. Villa Montosca sleeps 20, and the whole of La Poggiolaia sleeps 22. Villa Tavernaccia, Villa Chiara and Casa Bachicche each sleep 16, and Villa Amarika, Villa Colli and Villa Trionfante sleep 14. [See our full Italian Villa Rentals FAQ →](https://villavacations.com/italian-villa-rentals-faq/) Chianti — Reading ## From the *journal* DAY TRIP IDEAS ### Day Trip Ideas from Chianti FOOD & WINE ### The Olive Harvest in Italy: Three Weeks That Become a Year of Better Cooking FOOD & WINE ### Wine Tasting & Buying in Tuscany Explore ## Other *destinations* Each region is hand-picked, walked, and slept in by us first. See which one is calling. ### Amalfi *Coast* Costiera Amalfitana ### *Cortona* Under the Tuscan Sun ### *Florence* Renaissance Tuscany ### Lake *Como* Lakeside Elegance [See all destinations](https://villavacations.com/destinations/) --- Doorways Villa Vacations, Italian villa specialists since 1994. Book through a travel advisor: https://villavacations.com/contact-us/