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Chianti

Villa Chiara

An eight-bedroom Chianti villa with infinity pool, private spa, and the kind of fireplaces you actually use — set among olive groves halfway between Florence and Siena.

8 Beds
8 Baths
16 Guests

About This Villa

A spacious two-floor Chianti villa with adjoining annex, set halfway between Florence and Siena among olive groves. Traditional Tuscan interiors keep the original terracotta floors, stone walls, beamed ceilings, brick arches, and wood-burning fireplaces. Sixteen guests across eight en-suite bedrooms.

8 bedrooms / 8 en-suite bathrooms across main villa + annex

All bedrooms with air conditioning

A spacious two-floor Chianti villa with adjoining annex, set halfway between Florence and Siena among olive groves. Traditional Tuscan interiors keep the original terracotta floors, stone walls, beamed ceilings, brick arches, and wood-burning fireplaces. Sixteen guests across eight en-suite bedrooms.

The outdoor centerpiece is an infinity-edge swimming pool with a built-in whirlpool, framed by olive trees and looking out over the valley. A private spa wing — heated Jacuzzi, sauna, cardio gym, and a massage room — sits within the villa for cooler-weather afternoons. Three kitchens, multiple dining areas indoors and out, and the kind of fireplaces you actually use in October.

The nearest serviced town is six minutes away by car; from there, the must-see Chianti villages of Castellina, Radda, and Gaiole are an easy loop. Florence and Siena are each roughly forty minutes — close enough for day trips, far enough that you sleep in deep countryside silence.

Included in the rate: electricity (excluding air conditioning), water, midweek towel changes, spa access, wifi, and weekly garden and pool maintenance.

Electricity (excluding A/C), water, wifi

Midweek towel changes

Private spa access (Jacuzzi, sauna, gym, massage room)

Weekly garden and pool maintenance

Check-in: between 4:00 pm – 7:00 pm – Check-out: before/by 10:00 am

Inspiration to get you dreaming

Your concierge can help arrange unforgettable experiences tailored to your stay.

Chianti

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.

Chianti

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.

Chianti

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.

Chianti

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.

Chianti

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.

Chianti

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.

Availability

Pricing is per week, Saturday to Saturday. Diagonal cells mark changeover Saturdays — morning departure / afternoon arrival.

Available Booked Changeover (Saturday)

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Bring your Italian dream
vacation to life

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Weekly stays begin on Saturday
From
€11,460 for 7 nights

Got questions? Read our FAQ →

Castellina in Chianti

Chianti countryside, halfway between Florence and Siena

From €11,460 / week

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