Discover To Tuscany’s exquisite holiday rental villas set amidst rolling hills and Cypress trees.

Absence makes the heart grow fonder as the old adage goes. And, though our fondness for sun-drenched escapes to Tuscan idylls was hardly in need of rekindling, a two-year pandemic-induced hiatus has proven that absence does, indeed, make the prospect more longed-for than ever before.

As is well-documented, travel has been one of the hardest hit sectors amidst landscape of commercial damage wrought by the Covid-19 crisis. However, looking ahead, there are reasons to be cheerful, both for the industry and for those who have dutifully foregone foreign holidays throughout.

At the tail end of last year, research revealed that 57 per cent of British adults planned to take an overseas holiday in the next twelve months, a statistic that amounts to a 46 per cent rise on the previous year. The message is clear: confidence is returning – and that data was gathered even as the Omicron variant was on the rise. Now, as we pass its peak, the boom may yet be even greater than predicted.

It is a trend that has been more than amply reflected in the sheer volume of enquiries experienced by To Tuscany, specialists in sourcing the most exquisite Tuscan villas for holiday rental, which reports pre-pandemic levels of interest.

Founded at the turn of the millennium, it is run by married couple, Sean and Sabina, who opened the doors to their very first rental in a restored Chianti winery and haven’t looked back since; twenty years later, they have gathered considerable expertise and some 500 more villas, all of which retain the personal touch that made their inaugural venture so special.

For those who spent the various lockdowns dreaming of hefty medieval farmhouses set amidst Cypress tree-studded landscapes, all flooded with a Tuscany’s golden light (who didn’t?), now is the time to discover To Tuscany’s exceptional roster of properties.

Here we pick five of our very favourites.

Casa all'Erta

The classic Tuscan view should, by rights, feature at least one vineyard amidst rolling green hills. Situated on an estate belonging to the San Polo in Rosso castle, Casa All’Erta delivers spectacularly on that front; the ridge upon which it picturesquely sits lies between Chianti Classico vineyards, olive groves and oak forests, all carved through with streams and ancient mule tracks. For walkers, it is heaven. Happily, the same is true for the merrily indolent, too. Its exquisite situation is matched by the beauty of the property itself, which contains six double bedrooms (thus sleeping twelve), seven bathrooms and a private swimming pool. For those who want to unwind to the full, there is a sauna and a Turkish bath. But to simply watch the ways in which the landscape changes through the days as it is doused in morning, then afternoon, then evening light, would be plenty to sustain us – whether from the vantage point of the pool or the terrace. Book it here.

Podere Campi

Holidaymakers who enjoy their down time with a side helping of history will surely relish Podere Campi. In a former life, this magnificent stone structure served as a priest’s house and a strategic hilltop watchtower. The legacy of the latter is, of course, unsurpassed views across vineyards, olive groves and valleys. Nestled in woodland, it offers welcome shade in the heat of the day for sleeping and reading, while the medieval delights of Siena, San Gimignano and Florence are within easy reach for a day trip.

When not on cultural excursions, the beautiful house offers plenty by way of pleasurable distraction. Lying by its pool, situated on the lower garden terrace, would be a wholly reasonable use of a full day; by the time evening falls, one would only need wander up to the upper terrace for aperitivo hour under the shelter of a centuries-old mulberry tree, and watch the sun as it melts into the hills.

Sleeping ten to twelve people, the villa is arranged across three buildings, each of which blends country comfort with a minimalist sensibility. An ideal place for those travelling with friends or family who enjoy being together but having their own space, too. Book it here.

Lo Spicchio

New for 2022 comes this wonderful villa, which is perfect for those looking for a dreamy and cosy Tuscan idyll for two. Right in the heart of Chianti, it is situated a few minutes’ drive from the lovely Radda amidst the undulating verdant patchwork of olive groves and vineyards that is so characteristic of the area. There is a small hamlet within walking distance for a morning coffee; otherwise, we would hole ourselves up and revel in the gloriously green garden, private pool and ravishing views. Book it here.

La Mita

La Mita lies on the border of Tuscany and Umbria, just on the Tuscan side of the Niccone Valley. A beautiful and homely simple stone villa, it has three bedrooms (sleeping four to six) and exudes the rusticity and charm synonymous with the region.

The garden and private pool make this a great choice for a family, while the view is inspiring for anyone looking for a Tuscan getaway. The town of Mercatale di Cortona is just 10km away, while the beautiful towns of Perugia (35km) and Arezzo (50km) are within striking distance, too. Book it here.

Mulinaccio di Badia

Mulinaccio di Badia is the ultimate destination for oenophiles. Set on the sloping vines of the famous wine estate of Gaiole in Chianti, the villa overlooks the region’s famous seven castles, each of which is dotted amidst vineyards. An ancient stone farmhouse, it is framed by woods and Cypress trees, while its interiors are rustic and homely, thanks to the abundance of classic beams, terracotta tiles and shuttered windows. There are five bedrooms, a private pool and a beautiful al fresco area for dining amid the glorious setting. For those who cannot break with their fitness regimes, there is a gym; for everyone else, the order of the day is to sip exceptional local wines on the terrace. Opposite the main building is an open-sided barn which accommodates a kitchen and dining area in which to enjoy the region’s much-loved and lauded cuisine. Siena is just 25km away and Florence is 50km. Book it here.

By Nancy Alsop
January 2022

Nancy Alsop


Nancy is a magpie for the best in design and culture.