For those dreaming of a perfect fall getaway, we have the perfect curation of villas in Tuscany. Featuring views over landscapes that will transform into gorgeous golden and russet shades throughout the season, cosy interiors with fireplaces for snuggling up with a good book or a movie, and pretty gardens where you can still enjoy hearty meals al fresco for much of the season, these properties really allow guests to enjoy the beauty of Tuscany at this time of the year and to really lean into everything that we love about autumn! So, check out these perfect vacation rentals in Tuscany and plan an autumn break filled with stunning scenery, incredible harvest delicacies, gorgeous wines, and cooler weather that makes getting out and exploring dreamy landscapes like the Val D’Orcia, historic towns like Siena, and Florence’s endless list of tourist attractions more pleasant.
Barberino di Mugello
Sleeps up to 9
5 bedrooms
3 bathrooms
Surrounded by trees and greenery that will change shades throughout the season and put on a wonderful show, this villa boasts spacious but cosy interiors, open fireplaces, and a beautiful garden with several areas to sit out and enjoy the scenery. The area of Mugello in which the property is located is 40km north of Florence and a stone’s throw from the Apennines. A poetic, lush landscape, it has historically produced artists, is dotted by pretty towns with architectural wonders, and boasts delicious ingredients like flavourful mushrooms, chestnuts, milk, and more and delightful regional dishes made with them. The pool closes on the 15th of September but can be open outside this time frame upon request. With half of September 2026 still available and all of October and November currently free, it is an ideal time to book an autumnal getaway in Tuscany at this gem.
Botinaccio
Sleeps up to 6
2 bedrooms
2 bathrooms
This sweet villa, meanwhile, offers sweeping views over the lush landscape of the countryside 2km outside the centre of the town of Botinaccio. Just 27km from Florence, you have easy access to the city and all of its delights while still getting to escape from everything for a little while. The private pool at this villa is officially open until the end of September but can be extended and from the water you can enjoy those panoramic views over the surrounding olive groves, fields, hills, winding roads, and more. Al fresco dining on the terrace will also allow you to soak up the typical Tuscan scenery as it transforms with the season. Indoors, the exceptionally pretty interiors with exposed beam ceilings, stone feature walls, an open fire, bright colours, a country kitchen, and plush furnishings are all ideal for cosy evenings at home after days of exploring. September and October 2026 are both booked up but all of November is still free so book now if you’re interested before the final dates are snapped up!
San Giovanni D'asso
Sleeps up to 5
3 bedrooms
3 bathrooms
Located in the pretty and historic town of San Giovanni D'asso and boasting views over the famously lush and picturesque Val D’Orcia, Casa La Crete is ideally positioned for making the most of autumnal scenery and planning perfect days out in Tuscany. The villa is an easy day-trip distance from the renowned wine towns of Montalcino and Montepulciano and from the historic gem that is Siena. Plus, those aforementioned views can be enjoyed readily from the lovely terrace where there are plants and flowers, sweet decorative touches, a nice area to dine al fresco, a pool (open until the 15th of October), and sun loungers. Inside the charming stone and brick villa itself, you will find evocative and cosy Tuscan interiors with an open-plan living space, a large fireplace, exposed brick arches and exposed beam ceilings, thoughtful touches, and welcoming bedrooms. Currently, there are a handful of days free in both September and October and all of November is available so snap up your stay and come explore the natural beauty and culinary delights of the surrounding area before returning home to this sweet villa with truly spectacular views.
Torri
Sleeps up to 8
3 bedrooms
2 bathrooms
This charming stone villa boasts a private swimming pool (officially open until the 30th of September) in a lush and manicured little garden with a lovely area to dine al fresco on the terrace or on the porch. Located in the quaint town of Torri, just 14km from Siena, you get to enjoy natural surroundings and peace and quiet without giving up convenience or easy access to incredible attractions. Not only can you enjoy the well laid-out garden but the cosy interiors are ideal for a fall stay in a holiday rental in Tuscany with a big open fireplace, charming traditional details like brick arched ceilings and exposed stone walls, and incredibly plush and welcoming bedrooms. With all of autumn 2026 currently free to book, as well, it is an ideal option for securing the exact dates you prefer for an escape this year.