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Chianti
An entire Tuscan estate above Certaldo — five restored apartments sleeping 22, with a shared pool and panoramic San Gimignano views.
Villa La Poggiolaia is a hilltop farmstead in Certaldo, in the heart of Tuscany's so-called golden triangle between Florence, Siena and Pisa, with views across olive groves toward the towers of San Gimignano. Owner Paola has personally restored every apartment — marble, tiles, light fixtures, antique family furniture — and the result is a relaxed, atmospheric, lived-in place that feels nothing like a hotel.
The estate is built around five independent apartments, all sharing the same Mediterranean-style swimming pool (6 × 14 m) and the same flower-lined garden paths. You can book any single apartment, several at once, or the whole property — twenty-two guests across twelve bedrooms is the maximum capacity, with private terraces and entrances for each apartment so no one has to share.
The converted barn — sleeps 8, fireplace, piano in the sitting area.
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Sleeps 4, two bedrooms, four-poster bed and two terraces.
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Sleeps 4, two bedrooms, pastel interiors, two terraces.
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Sleeps 4, two bedrooms upstairs, ground-floor kitchen.
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The smallest — sleeps 2, single-storey, couples-suitable.
View apartment →A housekeeper is on the property throughout your stay, and complimentary wine tastings at the family's own cellar are included for every guest. Final cleaning, A/C, baby cots and pool towels are billed separately on arrival.
Property
La Poggiolaia is a hilltop estate just outside Certaldo, in the so-called golden triangle between Florence, Siena and Pisa, surrounded by olive groves and vineyards with views toward the towers of San Gimignano. The estate's gardens, the Mediterranean-style swimming pool, and the wide private parking are shared among all five apartments.
The Five Apartments
Capanna (sleeps 8, 12 bedrooms): the largest, in the estate's converted barn — fireplace, piano in the sitting area, four double bedrooms and a smaller twin upstairs, two terraces (north and south).
Nandina (sleeps 4, 12 bedrooms): a two-storey apartment with a four-poster bed upstairs and a double (convertible to twins) on the ground floor; two outdoor areas.
Mahonia (sleeps 4, 12 bedrooms): pastel interiors, both bedrooms convertible to twins, two terraces flanking the apartment.
Lavanda (sleeps 4, 12 bedrooms): both bedrooms upstairs (en-suite), living room with kitchenette and outdoor access on the ground floor.
Roseto (sleeps 2, 12 bedroom): the smallest apartment, entirely on the ground floor, with a private south-facing terrace — designed for couples.
Outdoors
Shared Mediterranean-style swimming pool with Roman steps, 6 × 14 m, open 30 April through 25 October. Olive groves and vineyards across the property. Wide private parking. Flower-lined garden paths between the apartments.
Estate Services
A housekeeper is on the property throughout your stay. Complimentary wine tastings at the family's wine cellar are included for every guest. The estate is rented Saturday-to-Saturday.
Heritage
Owner Paola has personally restored each apartment, mixing marble, terracotta and tile work with antique family furniture. Tuscan-coloured walls, baroque mirrors, French windows that let the sun in.
All utilities (electricity, water, gas)
House keeper present on site throughout your stay
Free wine tastings at the family farm in the nearby wine cellar
Garden and pool maintenance
Mid-stay linen and towel change
Wi-Fi indoor and outdoor
Shared Mediterranean-style swimming pool (6 × 14 m, open 30 April – 25 October)
Shared washing machine (free use)
On request: pre-arrival grocery provisioning, private cook, cooking classes, airport transfers
Extras (paid locally on arrival): end cleaning · A/C and heating if required · baby bed €100/week · pool towels €10 per towel
Saturday-to-Saturday rentals only
Children welcome (baby bed available on request, €100/week)
No pets
No smoking inside
Five apartments can be booked individually or as the whole property (sleeps up to 22 across 12 bedrooms)
Pool open 30 April – 25 October
Wide private parking on the property
Hilltop estate; the access is a country lane
Check-in: from 4:00 pm · check-out: by 10:00 am
Italian tourist tax: approximately €1.50–€5.00 per person per night for the first 7 nights (paid locally in Euro cash)
Your concierge can help arrange unforgettable experiences tailored to your stay.
Chianti
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
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
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
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
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
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.
"We had a fabulous time. The (villa) couldn't have been more beautiful. We found all your restaurant selections to be wonderful and were so glad we had so many choices so close."
"Our piece of paradise – Poggio delle Rose – as beautiful as I remember it. One year has flown by. Believe me, there is no better place on earth."
"What a place! It is a heavenly place. It really is the most beautiful place we have ever stayed, in every sense. I can only imagine when the roses and lavender are in full bloom."
A charming corner of Italy with a rich history, scenic coastline, and easy access to nearby villages, beaches, and day-trip destinations. Your travel advisor can help you plan every excursion to make the most of your stay.
Travel Advisor
From the right villa to private chefs, boat charters, and bespoke experiences, we take care of every detail.
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