Chianti · Florence · Siena · Val d’Orcia · Lucca · Maremma
Luxury Villas in Tuscany for Rent
Vineyards and hill towns, Renaissance cities and a quiet stretch of sea.
Dates not fixed yet? Tell us your 2027 month
2027 dates are open
2027 in Tuscany: the weeks that book first
Luxury travelers are booking further ahead than a year ago: in October 2026 Travel Weekly reported that a leading luxury operator’s median lead time in the US market has lengthened by 20%, and at Virtuoso Travel Week in August, advisors reported future leisure sales one and two years out up 50%.
For June to September and the holidays the large estates in Chianti, the Val d’Orcia and around Lucca are confirmed 9 to 12 months before arrival, so the summer of 2027 is being reserved now. Choose a week to see which villas are free, or tell us your month and how flexible you are.
Haute Retreats offers more than 100 luxury villas in Tuscany, from Chianti farmhouses and Val d’Orcia estates to staffed villas outside Florence and Lucca and houses by the sea in the Maremma. Every villa is visited by our team before we offer it, every villa on this page has a private pool, and every booking includes a 24/7 concierge. Tell us your dates and your group: a Tuscany specialist replies within 24 hours with three to five villas that fit, and their current rates.
Signature villas
Three signature Tuscany villas
A starting point, chosen to show the range: a Chianti house where the chef comes with the rent, a Renaissance estate outside Florence with a butler, and a Baroque villa near Siena for a large group.
Villa Le Masse
A stone house among the vineyards and olive groves of Panzano, with a magnesium salt-water infinity pool and a courtyard of lemon trees and jasmine around a historic wood-fired pizza oven. A chef cooks lunch or dinner every day, with a Saturday welcome dinner and a Wednesday pizza night. Seven-night minimum for most of the year.
Villa I Busini
A Renaissance estate of 40 hectares, half an hour by car from Florence, with frescoed salons, a library, a chapel, a tennis court and an infinity pool built from Tuscan stone. A butler, daily housekeeping and a Tuscan breakfast come with the stay, with a cook and a server for lunch or dinner.
Villa Cetinale
A 17th-century Roman Baroque villa 14 kilometers from Siena, with a formal garden, a private chapel, a tennis court and two kitchens. A private chef cooks every meal, with waiters and a porter, so the house runs like a private hotel. Seven-night minimum for most of the year.
Where to stay
Tuscany villas by area
Tuscany is large enough that the area shapes the week as much as the house does. This is how our specialists match a group to a part of the region.
Chianti
The wine country between Florence and Siena, around Panzano, Greve, Radda and Castellina: Chianti Classico estates, stone villages and long lunches under a pergola.
- Zietta9 bedrooms · sleeps 22
- Palladia6 bedrooms · sleeps 12
- Casale Felicità5 bedrooms · sleeps 10
Florence and its hills
Villas in the hills a short drive from the city, close enough for the Uffizi in the morning and dinner by the pool. Villa Ione is about 20 minutes from the historic center, and the top terrace of Villa Matteo looks across to the Duomo.
- Villa Matteo10 bedrooms · sleeps 22
- Villa Ione5 bedrooms · sleeps 10
- Casa Bachicche8 bedrooms · sleeps 16
Siena and the Valdelsa
The hills around Siena and Casole d’Elsa, within reach of Monteriggioni and San Gimignano, with some of our largest houses for reunions and weddings.
- Villa Elsa16 bedrooms · sleeps 32
- Villa Montosca10 bedrooms · sleeps 20
- Casale Cetena Rossa8 bedrooms · sleeps 16
The Val d’Orcia and Montepulciano
The UNESCO-listed valley of Montalcino and Pienza, where the Brunello comes from, and the hills of Montepulciano, with Bagno Vignoni a short drive away.
- Villa Teresa6 bedrooms · sleeps 12
- Il Principe7 bedrooms · sleeps 12
- Montalcino Palazzo4 bedrooms · sleeps 8
Lucca and the west
The countryside around walled Lucca, about half an hour from the beaches of the Versilia and close to Pisa airport. At several houses here a chef cooks breakfast and one other meal.
- Villa Contrada12 bedrooms · sleeps 24
- Medea14 bedrooms · sleeps 28
- Bernardini7 bedrooms · sleeps 14
The Maremma
Southern Tuscany on the coast: the Argentario and the lagoon of Orbetello, hill towns such as Capalbio and Pitigliano, and, at Via Del Mare, a path down to the sea.
- Via Del Mare10 bedrooms · sleeps 22
- Veltuna7 bedrooms · sleeps 14
- La Tenuta7 bedrooms · sleeps 16
Which part of Tuscany is right for you?
The short answer, area by area. A specialist will refine it once we know your dates and your group.
| Area | The feel | Best for | Our villas there |
|---|---|---|---|
| Chianti | Vineyards and stone villages | Wine, first visits, a central base | Villa Le Masse, Zietta, Palladia, Casale Felicità |
| Florence and its hills | The city close by | Art, restaurants, short drives | Villa I Busini, Villa Matteo, Villa Ione, Casa Bachicche |
| Siena and the Valdelsa | Medieval towns, large estates | Reunions, weddings, large groups | Villa Cetinale, Villa Elsa, Villa Montosca |
| The Val d’Orcia and Montepulciano | Open, quiet landscape | Wine, quiet and slow days | Villa Teresa, Il Principe, Montalcino Palazzo |
| Lucca and the west | A walled city, the coast nearby | Staffed stays, beach days | Villa Contrada, Medea, Bernardini |
| The Maremma | The sea and the hill towns | Beaches, space, privacy | Via Del Mare, Veltuna, La Tenuta |
Find the right villa
Find the right Tuscany villa
The questions guests ask us most, with the page that answers each one.
- Tuscany villas with a chefEleven villas where the chef is part of the rent, and exactly what each kitchen covers.
- Staffed villas in TuscanyWhat a staffed stay includes, compared house by house.
- Large villas for reunionsHouses for families and friends traveling together, and how to choose one.
- Villas near FlorenceHillside houses a short drive from the Renaissance city.
- Villas in ChiantiOur Chianti collection, between Florence and Siena.
- Michelin-starred restaurants in TuscanyWhere to book a table, from Florence and the wine country to the coast.
Celebrations for 20 to 40 guests
Tuscany villas for weddings and milestone birthdays
Celebration travel, from weddings and anniversaries to milestone birthdays, ranks second among the ultraluxe experiences in Virtuoso’s 2027 Luxe Report, drawn from more than 3,100 travel advisors in over 50 countries, and Italy ranks second among the destinations for 2027, after Japan. Our own calendar agrees: for 2027 our specialists are already planning two such weeks near Lucca, a 60th birthday for 32 guests in May and a 40th birthday in June. These are the houses we suggest for a party of 20 to 40, with what each offers for the dinners and the day itself.
Villa Rinascimento
A 14th-century hamlet 15 minutes from Florence, with 20 bedrooms in five buildings among 30 acres of vineyards, olive groves and woods, a spa, two pools and a helipad.
For the celebration. A frescoed chapel by Ridolfo del Ghirlandaio for a wedding or a milestone event, and a buffet breakfast every day in the villa’s own restaurant. The villa plans the event with you, and an event fee applies.
Villa Elsa
A restored grand villa in the hills near Siena, with a tennis court, a bocce court, a sauna, a whirlpool and several terraces for dining outdoors.
For the celebration. A coordinator and four members of staff six days a week, breakfast every day and a welcome cocktail with appetizers on Saturday; a cook can be added for the dinners. The house was made, it says, for reunions, anniversary parties and weddings.
Daniela
Eleven traditional bedrooms and a new wing of five, in an Italian garden with a large private pool, a 10-minute drive from Lucca.
For the celebration. A dining room that seats 22, a shaded patio and a professional kitchen, a continental buffet breakfast every day and, on weekly stays, a welcome buffet dinner with local wine. The cook comes from the villa’s own staff.
Davinia
A restored hamlet in the Chianti hills, with a pool facing the vineyards and olive groves, a spa, and salons and dining rooms for every season.
For the celebration. A panoramic terrace for dinners outdoors, an outdoor bar and a barbecue area. The house names weddings and milestone celebrations among the occasions it was made for, and meals are cooked by its own staff, with no outside suppliers.
Villa Cetinale
Parts of the villa date from 1651, with stately gardens around it. Fully staffed, with a private chef for every meal, the cost of the food aside.
For the celebration. The gardens take up to 120 people for a ceremony, cocktails, dinner and dancing, with the limonaia for about 70 if it rains, and a civil ceremony can be held in the garden. The house chef cooks for up to 30; beyond that, a caterer. An event fee applies, set by the number of guests.
Villa Contrada
An 18th-century residence with a lemon-tree courtyard and a park that runs out to the olive groves. Fully staffed, with a private chef for breakfast and one main meal a day.
For the celebration. A banquet room that seats the whole party at one table, a wine library for tastings and room for a long table under the trees. The house arranges pizzaiolo parties, cakes from a Lucca pasticceria, musicians, flowers and photographers.
Two more for 22 guests
- Villa GalileoNear Lucca · 11 bedrooms · sleeps 22A private chapel available for weddings, a banquet room, and a chef for breakfast and for lunch or dinner. Fully staffed.
- Podere TesoroNear Siena · 10 bedrooms · sleeps 22A main house and a guest house, with an events barn that has its own professional kitchen, an events terrace and a 22-meter infinity pool.
Events need the owner’s approval
A wedding, a party with outside guests or music late into the evening needs the owner’s approval, and many houses charge an event fee. We confirm what is allowed, and the fee, in writing before you book.
Who cooks
Most of these houses cook with their own staff, and some accept no outside suppliers. For a bigger table a caterer takes over: at Villa Cetinale the house chef cooks for up to 30.
Ceremonies
Villa Rinascimento has a frescoed chapel and Villa Galileo a private chapel available for weddings; at Villa Cetinale a civil ceremony can be held in the garden.
More guests than bedrooms
These villas sleep about two guests to a bedroom. If more will come to dinner than can stay, we look for a second house nearby for the rest of the party.
Book 9 to 12 months ahead for June to September, and 6 to 9 months ahead for spring and autumn. For company offsites and wellness retreats in Tuscany and beyond, see our group retreat villas.
Speak to a specialist
Speak to a Tuscany villa specialist
Tell us who is coming, the dates and what the week is for, from a family summer in Chianti to a wedding near Siena. The specialist who plans the stay replies within 24 hours with a private shortlist of houses our team has visited, and stays with you until you fly home. Behind every stay is our concierge team, led by Monica.
- Toll-free, US and Canada+1 888 279 6444
- Miami+1 305 432 1731
- WhatsApp, 24/7+39 333 206 5514
- Email[email protected]
The Haute Retreats difference
What a stay with Haute Retreats includes
Tuscany has thousands of villas to rent. What we add is knowing the houses, the planning before you arrive and the people on the ground while you are there.
Every villa visited by our team
We visit every Tuscany villa before we offer it, so the specialist who answers you knows the house, the rooms and the road to it, not only the photographs.
The Haute Standard
A 21-day pre-arrival protocol on every booking: preferences and dietary needs captured, the house team briefed, provisioning set, transfers timed to your flights, and a written run-of-stay before you leave home.
Every hour of service in writing
Staff and hours differ from villa to villa, and we set them out before you pay. At Villa Contrada, for example, the chef cooks breakfast and one other meal six days a week, with Wednesday off, and housekeeping comes every morning except Sunday.
A welcome in person
Every guest is greeted in person on arrival with a welcome amenity chosen for the house, and a member of the local team is on hand throughout the stay, while your 24/7 concierge books the chefs, the wine tastings, the drivers and the tables.
Destination guide
Tuscany villa rentals: the complete guide
Renting a villa in Tuscany is the way to live the region rather than tour it: breakfast on your own terrace, a wine estate down the road, a hill town in the afternoon and dinner by the pool. Tuscany ranks first in our Billionaire Villa Index 2026, ahead of Turks and Caicos and Lake Como.
Where the best villas are
Our villas cluster in six places. Chianti, between Florence and Siena, is vineyard country and a central base. The hills around Florence keep the city within half an hour. Around Siena and Casole d’Elsa are some of the largest estates, built for reunions and weddings. The Val d’Orcia, around Montalcino and Pienza, and the hills of Montepulciano are open and quiet. Around Lucca, several villas come with a chef, and the Versilia beaches are about half an hour away. In the south, the Maremma brings Tuscany down to the sea.
Villas for families and large groups
Most of our Tuscany villas have five to ten bedrooms. For larger groups, Villa Rinascimento sleeps 37, Villa Elsa and Daniela 32 each, Davinia 30, Medea 28, Villa Cetinale 27 and Villa Contrada 24, and Zietta, Villa Matteo and Via Del Mare each sleep 22. Zietta spreads its nine bedrooms across a main house and two guest houses, and Villa Contrada and Villa Galileo near Lucca have the use of tennis, soccer and volleyball fields.
Getting to Tuscany
Florence and Pisa airports serve most of the region, and Rome is the gateway to the south: Via Del Mare, on the Maremma coast, is about an hour and forty minutes from Rome airport. From the United States, guests connect to Florence or Pisa through a European hub, fly into Rome, or fly private. Most villas are in the countryside, so plan on a car, or let your concierge arrange a driver for the days in Florence and Siena, and transfers timed to your flights.
Staff, chefs and minimum stays
Housekeeping is part of most Tuscany villa rentals, and its hours are set out for each house before you book. At eleven of our villas a chef is part of the rent, among them Villa Le Masse, Villa I Busini, Villa Cetinale, Villa Contrada, Bernardini, Il Principe, Veltuna and Via Del Mare; at most of our other houses we arrange a chef for as many meals as you like. Several villas ask for seven nights for most of the year, including Villa Le Masse, Villa Cetinale, Villa Contrada and Medea, and Zietta books Saturday to Saturday. We confirm the minimum for your dates in writing.
When to go
The best time to visit Tuscany
Tuscany is a villa destination all year. Each season suits a different trip.
Spring
Wildflowers, mild days of about 59 to 77°F and fewer visitors than in summer, with Easter in Florence and the Scoppio del Carro.
High summer
Long days by the pool, the Palio in Siena on July 2 and August 16, and Puccini under the stars at Torre del Lago. The weeks that book first.
The harvest
The grape and olive harvests, golden hills and, in October and November, the truffles of San Miniato.
Winter
Christmas markets in Florence and Siena, the Uffizi without the crowds, and long dinners of ribollita and bistecca alla fiorentina.
Book 9 to 12 months ahead for June to September and the holidays, and 6 to 9 months ahead for spring and autumn.
September and October
Villa rentals in Tuscany in September and October
Fall has become a season of its own. In August 2026 Virtuoso, the luxury travel network, reported fall bookings up 59% on the year before and fall bookings to Europe up 49%, with Italy second only to the United States among the most-booked countries for fall. In Tuscany, September and October are the months of the harvest.
The weather
Florence averages 79°F by day in September and 68°F in October, with nights of about 57°F and 50°F. September is still a month for long lunches outside and the pool; October has more rain, and a heated pool or a fireplace is worth asking for.
The harvest
In Chianti the Sangiovese grapes are picked between September and October, and the Expo del Chianti Classico fills the main square of Greve in Chianti on the second weekend of September. From late September the olive harvest begins, and the new oil is pressed through the autumn.
The villa for the season
For the harvest, choose a house among its own vines and olive trees; for October, a heated pool or a spa. Each of these four has at least one of them.
Four Tuscany villas for the harvest
- ZiettaCastellina in Chianti · 9 bedrooms · sleeps 22Three hectares of its own vineyard, olive and fruit trees, and a heated infinity pool; the heating charge is confirmed at booking.
- PalladiaRadda in Chianti · 6 bedrooms · sleeps 12The Carleone vineyard begins at the edge of the garden, and the pool is heated.
- Villa TeresaNear Montepulciano · 6 bedrooms · sleeps 12A running track through the vineyards, and an indoor spa with a heated pool, a sauna and a hammam.
- La TenutaThe Maremma · 7 bedrooms · sleeps 16A working estate that makes more than 60,000 bottles of wine and 10,000 liters of extra virgin olive oil a year, with a sauna and a Jacuzzi.
Book 9 to 12 months ahead for September, and 6 to 9 months ahead for October.
Questions
Tuscany villa rentals: your questions answered
What is the best area to rent a villa in Tuscany?
It depends on the trip. Chianti is a central base, between Florence and Siena; the hills around Florence suit art and restaurants; Siena and the Valdelsa have large estates for reunions; the Val d'Orcia is open and quiet; Lucca has several villas with a chef included; and the Maremma is Tuscany by the sea.
How far in advance should we book a villa in Tuscany?
Nine to twelve months ahead for June to September and the holidays, and six to nine months ahead for spring and autumn. The large estates and the weeks of July and August go first. Our 2027 calendar is open: tell us your month and how flexible your dates are, and we confirm which villas are free within 24 hours.
Is September or October a good time to rent a villa in Tuscany?
Yes, it is the harvest season. In Chianti the Sangiovese grapes are picked between September and October, the Expo del Chianti Classico is held in Greve on the second weekend of September, and the olive harvest begins from late September. Florence averages 79°F by day in September and 68°F in October, with more rain in October, so a heated pool or a spa matters: Zietta, Palladia, Villa Teresa and La Tenuta are four of our villas for the harvest. Book 9 to 12 months ahead for September and 6 to 9 months ahead for October.
Can we celebrate a wedding or a milestone birthday in a Tuscany villa?
Yes, at villas that accept events, with the owner's approval and usually an event fee, confirmed in writing before you book. For 20 to 40 guests, Villa Rinascimento near Florence has a frescoed chapel for weddings and milestone events, Villa Cetinale near Siena hosts up to 120 people in its gardens and allows a civil ceremony there, and Villa Contrada near Lucca has a banquet room that seats the whole party at one table.
Are there villas in Tuscany for large groups?
Yes. Villa Rinascimento sleeps 37, Villa Elsa and Daniela 32 each, Davinia 30, Medea 28, Villa Cetinale 27 and Villa Contrada 24, and Zietta, Villa Matteo and Via Del Mare each sleep 22. Most of our other Tuscany villas have five to ten bedrooms.
Can we rent a villa in Tuscany with a private chef?
Yes. At eleven of our Tuscany villas a chef is part of the rent and you pay only for the food: at Villa Cetinale the chef cooks every meal, and at Villa Le Masse lunch or dinner every day. At most of our other houses we arrange a chef for as many meals as you like.
Is there a minimum stay for Tuscany villas?
Often, yes. Villa Le Masse, Villa Cetinale, Villa Contrada and Medea ask for seven nights for most of the year, and Zietta books Saturday to Saturday. We confirm the minimum for your dates in writing.
Which part of Tuscany is best for families?
Chianti and the hills around Florence and Lucca, where the drives are short and the villages close. Zietta has room for 22 across a main house and two guest houses, and Villa Contrada and Villa Galileo near Lucca have the use of tennis, soccer and volleyball fields.
How do we get to a Tuscany villa from the United States?
Connect to Florence or Pisa through a European hub, fly into Rome, or fly private. Your concierge arranges the transfer from the airport to the villa, timed to your flight, and a driver for the days in Florence and Siena.
How much does it cost to rent a luxury villa in Tuscany?
It depends on the villa, the week and the level of service, from a serviced farmhouse to a staffed estate with a chef. We quote current rates for your dates, with the staff and services included set out in writing.
The journal
Plan your trip: our Tuscany guides
Plan your Tuscany villa stay
Tell us your dates and your group: a Tuscany specialist replies within 24 hours with three to five villas that fit, and their current rates.
Toll-free, US and Canada +1 888 279 6444 · Miami +1 305 432 1731
Collection updated October 2026