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.
Tuscan Flow
4 guests
2 bedrooms
Castelnuovo Berardenga, Siena
Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court.
Beneath The Autumnal Sun
10 guests
5 bedrooms
Castelnuovo Berardenga, Siena
Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide.
Tuscan Haven
2 guests
2 bedrooms
Sovicille, Tuscany
Situated a short drive outside the bustling medieval city of Siena, this villa offers a true escape in the Tuscan countryside. Originally constructed as a watchtower, its 12th-century exterior has been updated with a stunning glass pavilion that offers 270-degree views of rolling Tuscan hills covered in cypress trees and olive groves.
Explore the 3328 most perfect homes in our collection
Explore our incredible collection of Vacation Rentals for Autumn in Siena, Tuscany, Italy. Nothing gets past our experts, with each home being put through 3 rounds of vigorous testing before being accepted into our range. With everything from shower pressure to a space's design being inspected, it's no surprise that our collection is the best of the best. Each rental on our books come fully furnished, with a well-equipped kitchen, essential bathroom toiletries, and all linen included. Book your luxury Autumn Holiday Rental in Siena today, and mark the season with a trip to remember. Reach out to our team of friendly experts, too - they love nothing more than helping you find your dream home.
