The Alighieri
4 guests
2 bedrooms
Torrita di Siena, Siena
This converted Tuscan home provides a great base to explore one of Italy’s most iconic areas from. Though the interior perhaps lacks a bit of cosiness, it is well-kept and provides you with all you need for a comfortable stay, including a fully-equipped kitchen and a nice open-plan dining area which leads onto a private terrace.
Il Doppio
6 guests
6 bedrooms
Montepulciano, Siena
There's nothing more magical and romantic than the sight of an ancient hilltop Tuscan town, surrounded by rolling hills and cypress trees, and here it's what you'll be waking up to each morning. Set just outside the walls of Montepulciano, surrounded by vineyards and olive trees, this traditional farmhouse has been lovingly modernised by your host to create a perfect, authentic experience of life in this beautiful region.
Sunflower Sunset
8 guests
4 bedrooms
Pienza, Siena
In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside.
Ethereal Tuscan View
4 guests
2 bedrooms
Monticchiello, Pienza
Tucked within the medieval walls of Monticchiello, this Tuscan flat makes for an authentic countryside escape. With terracotta tiles, wood-beamed ceilings and a cosy fireplace, the interiors feel warm and welcoming – while the private garden, complete with dining area and barbecue, invites sunny afternoons relaxing and sunset aperitivos.
Explore the 3254 most perfect homes in our collection
Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Pienza, Siena, Tuscany, Italy. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Pienza Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.
