The Chianti Hills
8 guests
4 bedrooms
Gaiole in Chianti, Siena
This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves.
Sunlight in Tuscany
5 guests
2 bedrooms
Siena, Tuscany
This charming home was renovated from the owner’s ancient stable. It’s now a delightful holiday home perfect for a family or a group of friends.
Bellissima Casa
4 guests
2 bedrooms
Sovicille, Tuscany
Restored by an Italian architect with a gentle touch, this villa has been updated and split into more modern apartments, but without ever compromising on the original charm. By honouring the villa's history – and thereby retaining its character – the home feels traditionally Tuscan with its terracotta tiles and wooden beams.
Chianti Kisses
8 guests
4 bedrooms
Castelnuovo Berardenga, Siena
Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below.
Explore the 3974 most perfect homes in our collection
Looking for guesthouse style accommodation in Siena, Tuscany, Italy? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Siena, Tuscany, Italy has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
