Explore our handpicked villas in Tuscany across Chianti, Val d’Orcia, Florence and beyond — private pools, dedicated concierge and tailored experiences in one of Italy’s most captivating regions.
Live availability & pricing · or call +1 888 279 6444 , or WhatsApp our Italy office— our concierge will curate a Tuscany selection for you.
A handpicked selection of our finest luxury villas Tuscany — private chefs, fully staffed estates and homes within walking distance of charming towns.
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 ›Discover the most charming corners of Tuscany — each offering its own luxury villas, cultural treasures and unforgettable Tuscan views.
Historic architecture and cultural richness, with elegant estates in the surrounding hills.
Discover › Wine Country ChiantiVineyards, wine estates and countryside tranquillity — the heart of Tuscan villa life.
Discover › Medieval Hills Siena & Val d’OrciaMedieval hill towns and the golden Val d’Orcia — the Tuscany of postcards.
Discover › Authentic Charm LuccaWalled-city elegance and authentic charm, off the beaten path among olive groves.
Discover › Hilltop Wine Town MontepulcianoRenowned for its Vino Nobile and sweeping Val d’Orcia views — a wine lover’s base.
Discover › The Full Collection All Tuscany VillasExplore every villa across Chianti, Florence, Siena, Lucca and the Val d’Orcia.
View Collection ›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 ›Step into the timeless beauty of central Italy with our curated collection of luxury villas Tuscany. Every one of our villa rentals in Tuscany is visited before it is offered. At Haute Retreats we deliver more than holiday homes — unforgettable experiences across iconic destinations like Florence, Chianti, Siena and the Val d’Orcia. Each villa is handpicked for its architectural charm, premium amenities and stunning countryside views.
Family-friendly villas with poolside estates and safe outdoor spaces; romantic, secluded and fully serviced honeymoon villas; and group villas accommodating 18+ guests in comfort and style. Whatever the occasion, our Tuscany villa rentals offer an elevated way to experience the region.
Currency is the euro; voltage is the 220–240V European standard. Tuscany villas typically have a 7-night minimum, and many guests enjoy basing themselves in two regional spots — north and south — to explore fully. Our concierge arranges every transfer, chef and experience.
Blooming vineyards, mild weather (63–79°F) and fewer crowds — the ideal time for a countryside villa stay.
Festivals and warm evenings. Perfect for poolside living and exploring hilltop towns at dusk.
Harvest season — the grape and olive harvests, soft light and the most beautiful Tuscan colours of the year.
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.
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.
Not all villas include a private chef as standard, but many Haute Retreats properties offer chef service as an optional add-on. You can request a chef at the time of booking for a fully personalised culinary experience.
Absolutely. Many of our luxury villas in Tuscany are ideal for large families and groups, offering spacious accommodations, expansive outdoor areas and family-friendly amenities. Some villas host up to 18 guests comfortably.
Tuscany villa rentals range widely — from around $1,750 per night for charming countryside homes to $14,500+ per night for fully staffed historic estates. Most of our properties fall between $3,000 and $10,000 per night, with transparent pricing.
Chianti for vineyards and wine estates; Florence for culture and Renaissance charm; Siena and the Val d’Orcia for medieval hill towns and golden landscapes; Lucca and Montepulciano for authentic charm off the beaten path. Our holiday villas in Tuscany span all five, so the region you choose sets the pace of the week rather than limiting the house.
“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 — rated 5 out of 5.
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.