Chianti · Val d'Orcia · Florence · Siena
Luxury villas Tuscany — the timeless beauty of central Italy.
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 and our concierge will curate a Tuscany selection for you.
From Chianti to Val d'Orcia
Discover the most charming corners of Tuscany — each offering its own luxury villas, cultural treasures and unforgettable Tuscan views.

Renaissance City
Historic architecture and cultural richness, with elegant estates in the surrounding hills.
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Wine Country
Vineyards, wine estates and countryside tranquillity — the heart of Tuscan villa life.
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Medieval Hills
Medieval hill towns and the golden Val d'Orcia — the Tuscany of postcards.
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Authentic Charm
Walled-city elegance and authentic charm, off the beaten path among olive groves.
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Hilltop Wine Town
Renowned for its Vino Nobile and sweeping Val d'Orcia views — a wine lover's base.
Discover ›The Full Collection
Explore every villa across Chianti, Florence, Siena, Lucca and the Val d'Orcia.
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Featured Properties
A handpicked selection of our finest luxury villas Tuscany — private chefs, fully staffed estates and homes within walking distance of charming towns.

Chianti · Florence
from $14,500 / night

Chianti · Florence
from $9,600 / night

Barberino Val d'Elsa · Chianti
from $4,600 / night
Why Book With Haute Retreats

Destination Guide
Step into the timeless beauty of central Italy with our curated collection of luxury villas Tuscany. 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.
When to Visit
April–May brings blooming vineyards, mild weather (63–79°F) and fewer crowds — the ideal time for a countryside villa stay.
Long golden days, festivals and warm evenings. Perfect for poolside living and exploring hilltop towns at dusk.
September–October is harvest season — the grape and olive harvests, soft light and the most beautiful Tuscan colours of the year.
The Map
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.
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Guest Reviews
"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.
The Tuscany Journal
Begin the Conversation
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.