Haute Retreats offers more than 100 luxury villas across Tuscany, from Chianti farmhouses and Val d’Orcia estates to staffed villas outside Florence and houses near the sea in the Maremma. Our team visits every villa before we offer it, and every villa on this page has a pool. 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.
Search live availability · or call +1 888 279 6444 , or WhatsApp our Italy office — our concierge will curate a Tuscany selection for you.
Collection updated September 2026
Our signature Tuscany houses, each the one we suggest first for a different kind of week: a chef-led week in Chianti, a Medici estate with full staff, and a house for up to twenty-two.
A thirteenth-century house at the centre of Chianti, with a magnesium salt-water infinity pool, a courtyard of lemon trees and a 14th-century pizza oven built into the wall. The estate grows its own olive oil, vegetables and eggs, and that is what the kitchen cooks with. Includes a chef for one meal a day, a Saturday welcome dinner and a Wednesday pizza night.
View Villa Le Masse ›
A Peruzzi de’ Medici estate in the Chianti hills between Florence and Siena, fully staffed with a chef included in the rate — the reference point in our Tuscany collection for historic architecture with modern service.
View Villa I Busini ›
Nine bedrooms across a main stone farmhouse and two guest houses, ten minutes from Castellina in Chianti and fully renovated in 2021. Three hectares of olive groves, and a west-facing pergola terrace with a table for twenty — so dinner comes with the sunset. The most capable house here for a reunion or a wedding party.
View Villa Zietta ›Start with the part of Tuscany that suits the week, then choose the house. Each area opens onto its full collection, with three villas to begin with.
Wine CountryVineyards, wine estates and hill villages between Florence and Siena — the heart of Tuscan villa life.
By town: Panzano · Greve in Chianti · Tavarnelle Val di Pesa
See all Chianti villas ›
Renaissance CityEstates in the hills around the city, close enough for the Uffizi in the morning and dinner back at the villa.
Medieval HillsMedieval Siena and the hills of the Valdelsa, from Casole d’Elsa to the towers of San Gimignano.
By town: Casole d’Elsa
See all Siena villas ›
Brunello CountryThe Val d’Orcia of the postcards, with Brunello in Montalcino and Vino Nobile in Montepulciano.
By town: Montepulciano · Castiglion del Bosco · San Casciano dei Bagni
See all Val d’Orcia villas ›
Walled CityWalled Lucca, the spa town of Montecatini and the Pisan hills, with the sea within the hour.
Tuscany by the SeaSouthern Tuscany with the sea: open country, hill towns and the beaches of the Argentario coast.
Six ways to narrow the search, each with its own guide.
Every villa on this page has a pool. Several are heated, the one at Via del Mare looks out to sea, and Podere Tesoro adds an indoor pool.
Villa I Busini includes a chef, and Villa Le Masse a chef for one meal a day. At most of our other villas we can arrange one for as many meals as you like.
A house manager, a chef and daily housekeeping, so nobody in the group has to run the week.
Villa Davinia sleeps 32, Medea 28, Villa Cetinale 27 and Villa Zietta 22: room for the whole family under one roof.
Room for three generations, and a concierge who sorts the cots, the high chairs and the cooking class before you land.
Villas in the hills outside the city, such as Casa Bachicche and Villa Matteo, so the Uffizi and dinner by the pool fit in one day.
Tuscany stays are planned by our founder, Sabrina Piccinin, and her team in Italy. Call, WhatsApp or email, and you will speak to someone who knows the houses.
The gate is already open when the car turns off the strada bianca. Bags go up without being asked about. Somebody has decided which room the grandparents should have, and they were right. On the table there is wine from the estate three kilometres down the hill, because a conversation in April mentioned that you preferred Sangiovese to anything imported.
None of that is luck, and none of it is improvised on the day. It is the part of a villa holiday a guest is never meant to see.
“Luxury, at its highest level, is invisible. When something is done truly well, the client never notices the effort.”
Sabrina Piccinin, Founder & CEO — interviewed in EGW Luxury Magazine, The Legacy IssueOur work on your stay begins three weeks out, not on arrival day. Menus and dietary needs go to the chef. Bedrooms are allocated around who is travelling — light sleepers away from the terrace, grandparents on the ground floor, teenagers where the wifi actually reaches. Transfers are timed to your flight rather than to a checkout hour. Cots, high chairs, provisioning, the cook’s market day, the vineyard that needs booking six weeks ahead in September: all of it is settled before you land, by one specialist who has been to the house.
A family moving between Florence, the coast and Lake Como should not have to coordinate a villa company, an aviation provider, a chef, a local concierge and a driver separately. One point of contact stays with you across the whole journey, reachable by phone, WhatsApp and email while you are travelling — and where a private jet or a yacht is part of the plan, it is arranged inside the same system rather than alongside it.
We will not add more villas to the collection than our team can genuinely know, evaluate and stand behind. That is a limit on growth, deliberately, and it is the reason a specialist can tell you which house has the privacy its photographs imply and which one only looks large in the plan. Anyone can show you a thousand villas in Tuscany; the useful thing is knowing which four are right for your week. EGW Luxury Magazine reports that approach has produced an 80 percent guest return rate — which in a business built on discretion says more than any award.
What is left, when it is done properly, is a week in which nobody in your family has to organise anything. That is the whole ambition.
Tuscany ranks first in the Billionaire Villa Index 2026 — ahead of Turks & Caicos, Lake Como and the Amalfi Coast. Our own booking data shows why: no region in the collection has deeper staffed inventory, or holds demand later into the year.
Read the Index ›Tuscany is big enough that the area you choose shapes the week as much as the house does. The Maremma coast is about two hours by car from Florence, so most guests pick one base, or two for a longer stay, one in the north and one in the south. Every one of our villa rentals in Tuscany is visited by our team before it is offered, which is how we can tell you which house suits which week.
Most Tuscany villas are let by the week, often Saturday to Saturday, with a seven-night minimum in summer. The countryside is the point, so plan on a car, or let us arrange a driver for the days in Florence and Siena and transfers from Florence, Pisa or Rome airports. Currency is the euro; voltage is the 220–240V European standard. Our concierge books the chef, the wine tastings and the restaurant tables before you land.
Blooming vineyards, mild weather (63–79°F) and fewer crowds — the ideal time for a countryside villa stay.
Long days by the pool and dinners outside, and Siena’s Palio on 2 July and 16 August. The busiest weeks, so the best houses go first.
Harvest season — the grape and olive harvests, soft light and the most beautiful Tuscan colours of the year.
White truffles around San Miniato in November, new olive oil and fireplaces. Fewer villas stay open, so book Christmas early.
From Florence and the Chianti hills to Siena, Lucca and the golden Val d’Orcia — every corner of Tuscany within easy reach, each with its own character and its own collection of villas.
We quote rates for your dates rather than publishing them, because the same house can differ widely between May and August, and with the level of service you choose, from a serviced farmhouse to a fully staffed estate with a chef. Most Tuscany villas are let by the week, with a seven-night minimum in summer. Tell us your dates and your group and we will send a shortlist with current rates within 24 hours.
At this level, almost always. Every villa on this page has a pool: several are heated, Villa Le Masse has a salt-water infinity pool, the pool at Via del Mare looks out to sea, and Podere Tesoro adds an indoor one. If a pool used by your group alone matters, say so when you ask and we will only suggest houses where it is.
Yes. At Villa I Busini a chef is included in the rate, and at Villa Le Masse the rate includes a chef for one meal a day, a Saturday welcome dinner and a Wednesday pizza night. At most of our other Tuscany villas we can arrange a private chef for as many meals as you like, from a single dinner to three meals a day, and we send your menus and dietary needs ahead.
For a family or a group staying a week, a villa: you have the whole house, meals happen when and where you want them, and nobody has to meet in a lobby. A hotel makes more sense for one or two nights in Florence or Siena, or for a couple who wants a restaurant and a spa downstairs. Many guests do both: two nights in the city, then a week at the villa.
Chianti for vineyards and wine estates; Florence for culture and Renaissance charm; Siena and the Valdelsa for medieval hill towns; the Val d’Orcia, with Montalcino and Montepulciano, for golden landscapes and great wine; Lucca and the west for walled-city elegance; and the Maremma for the sea. Our holiday villas in Tuscany span all six, so the area you choose sets the pace of the week rather than limiting the house.
The best time is mid to late spring (April to May) and early autumn (September to October). These seasons offer mild weather, stunning scenery and fewer tourists, perfect for a relaxed, authentic experience. July and August are the busiest weeks, and the large estates book first.
It depends on your group and your week, but our three signature houses cover most wishes: Villa I Busini, a fully staffed Peruzzi de’ Medici estate with a chef included; Villa Le Masse in Panzano, for a Chianti week with a chef for one meal every day; and Villa Zietta near Castellina in Chianti, for a group of up to twenty-two.
Usually, yes. Most villas are in the countryside, and a car is the easiest way to reach the villages, wineries and restaurants around them. If nobody wants to drive, we arrange drivers for the days in Florence or Siena, and transfers from Florence, Pisa or Rome airports.
For June to September, nine to twelve months ahead: the large and fully staffed estates are usually the first to go. For spring and autumn, three to six months is often enough. Shorter notice can still work, so ask us: we know which houses still have weeks open.
It depends on how much help you want. Large booking sites list thousands of houses and leave the arrangements to you and the owner. Specialist villa companies list fewer houses, have been to them, and handle the chef, the transfers and anything that goes wrong during the stay. Whichever you use, check that someone has visited the house, that rates and terms are in a written agreement, and that recent reviews talk about the service, not only the photos. We visit every villa we offer, and our guests rate us 5.0 on Trustpilot.
“Sabrina organised the most luxurious, professionally arranged vacation for our family. We have rented villas around the world and this was the best by far.”
“If you want the most amazing time, go with Haute Retreats. Sabrina is understanding, kind, patient and very true to her word.”
“Sabrina was amazing. She found us the perfect villa and the staff were amazing. Best trip I have ever been on — highly recommended.”
Verified reviews from Trustpilot , where Haute Retreats is rated 5.0 out of 5. Nominated in the 2026 Condé Nast Traveler Readers’ Choice Awards.
No payment required — just tell us your preferences and our concierge team will reply within 24 hours with a curated shortlist of 3–5 villas .