
The Vine Vineyard
18 guests
11 bedrooms
Castelnuovo Berardenga, Siena
This gorgeous home boasts its own private pool and breathtaking valley and vineyard views. Ideal for families and large friend groups, there's plenty of space indoors and out.

The Vine Vineyard
18 guests
11 bedrooms
Castelnuovo Berardenga, Siena
This gorgeous home boasts its own private pool and breathtaking valley and vineyard views. Ideal for families and large friend groups, there's plenty of space indoors and out.

Golden Meadow
10 guests
5 bedrooms
Gaiole in Chianti, Siena
Nestled in the heart of Italy's Chianti region, this traditional Tuscan farmhouse, which was once a working mill, offers both character and charm. With wooden beams, exposed stone walls, and terracotta tiles, rustic appeal is aplenty here.

Super Tuscan
14 guests
7 bedrooms
Castelnuovo Berardenga, Siena
Whether you're swimming laps in the pool, lounging in bed or sipping a sundowner in the garden, this country home serves up breathtaking views from almost every angle. Surrounded by olive groves, world-famous vineyards and just a short drive from Siena, it’s a picture-perfect base for exploring the Chianti region.

Antipasti on the Patio
14 guests
6 bedrooms
Monteriggioni, Siena
Just 11km outside of Siena, nestled on a hilltop in the Tuscan countryside, you'll find this idyllic villa. It's a gorgeous spot with over a thousand square metres of grounds to explore, and plenty of space for your friends and family to roam.
Explore the 1952 most perfect homes in our collection
All Plum Guide houses in Siena, Tuscany, Italy have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each house in Siena, Tuscany, Italy before approving it, so you can book with peace of mind.