A Glass of Brunello
10 guests
5 bedrooms
San Miniato, Pisa
This rural, pet-friendly villa offers equal amounts of elegance and tradition. Accessed through an electric gate and up an avenue of olive trees, you'll enjoy privacy and tranquillity on the outskirts of Siena.
Siena Charm
8 guests
4 bedrooms
Siena, Tuscany
The quintessential Tuscan villa, this hillside four bedroom home looks out over the verdant Val d'Orcia. Ideal for families or friend groups seeking an authentic taste of Italian country life, the house sleeps eight and offers plenty of space for work, rest and play.
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.
Sunset on the Landscape
8 guests
4 bedrooms
Siena, Tuscany
Take a look at the amazing views of the Tuscan hills and Siena from this traditional home – they really do stop you in your tracks. The gardens are a dream as well – perfect for alfresco dining and drinks as the sun sets on the stunning landscape beyond.
Explore the 3726 most perfect homes in our collection
Browse our remarkable collection of luxury Vacation Rentals for Winter in Siena, Tuscany, Italy. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Siena. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.
