Best Luxury Villas in Tuscany to rent

Tuscany is the queen of the Italian regions, with 7 UNESCO world heritage sites, amazing art, landscape, food and wine. The perfect place for a luxury villa holiday, a chance to soak up the beauty of the region with the help of chefs, winetasting tours, cookery courses and city tours.

Here is our selection of Five Best Luxury Villas in Tuscany. They all have Private Pools, and we've also selected them on the basis of service - a luxury villa needs to have a high level of service, with an on-site concierge as well as our own concierge service.

These are all houses that we've visited - many times in most cases - so feel free to ask us any questions about the houses themselves or about the area!

1. Pipistrelli

Only a few kilometres south of Siena, Pipistrelli is a stunning conversion of a large Tuscan farmhouse. A New York designer turned this ancient secular building into a stylish luxury villa for 14, with an infinity swimming pool that looks out over the valley of the Merse river. The setting is utterly Tuscan and fabulously private - the drive up to the house crosses olive groves on a track lined with cypresses before diving into a dark holm oak forest that protects your privacy and makes you feel snug and safe from the world. Then the view from the pool opens out onto a valley with no buildings, just a river snaking through.

View over the Merse
Infinity Pool over the Merse

The house is part of the estate of Montestigliano and has the same fabulous concierge who can organise meals, tours, babysitting, and anything else you might need.

This is a popular villa - book early!

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2. Valdera

Tuscany is known for its amazing landscape and fabulous views. This luxury villa has some of the best, looking out over the Valley of the river Era towards the ancient Etruscan hill-top city of Volterra. I love the Villa Valdera because the owner really takes care over everything she does - the houses has large bedrooms, everyone of them ensuite, the kitchen is a chef's delight and there are lots of spots to sit and relax around the house. Visitors also love it because the tiny hamlet nextdoor has a restaurant that's just an easy stroll away. There's a great pleasure in leaving the car on the driveway and just walking out for dinner in the evening.

Valdera Luxury Tuscan villa near Valdera

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3. Cipressi

This is a new arrival for us and is stunning. Very close to Siena, on the road that heads out west, between Chianti and the Valdorcia. The house comes with everything that you'd want in a luxury villa, yet has still been converted with a light touch, leaving enough of the old farmhouse to give you an authentic Tuscan experience.

Cipressi is a very elegant villa near Siena

As with all these villas, services are not a problem - chefs, cookery courses, massages, city tours can all be easily arranged.

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4. Podere Castello

The forested hills of Chianti have long exerted their siren call over lovers of good wine, good food and beautiful views. Podere Castello is set in a privileged position, high on a hill with views of vineyards, forests of evergreen oak, and the fortified church that once protected this small hamlet.

Today this ancient stone farmhouse has been transformed into an elegant home for fourteen guests in spacious en-suite bedrooms. One of these bedrooms is fully accessible, making this house ideal for groups or families where somebody has limited mobility. The private swimming pool has stepped access so all can enjoy the views of Chianti from the infinity edge.

Podere Castello, luxury for 14 in Chianti

There is another luxury Chianti villa close by that can be taken with Podere Castello if you have a larger party; Borgo Castello sleeps 20 and also has a pool and jacuzzi.

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An aerial sketch of Borgo Castello

5. Villa Alessandro

This luxury Tuscan villa sleeps 11 and is set in a privileged position on the slopes of Mont'Albano, above Monsummano Terme. The views are spectacular and can be enjoyed from the covered loggia or from the large private swimming pool, with an infinity edge and a large hydromassage area for 8 guests.

Villa Alessandro above Montecatini Terme

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To see more luxury villas, have a look at our entire collection here: Luxury Villas in Italy