Perfect Tuscan Vacation Rentals For A Cosy Autumn Getaway

Villa Della Meletta, interior

Maybe you just didn’t get around to making a holiday happen this summer, perhaps you were put off by busy airports and tourist crowds, you might simply be in need of another vacation during mid-term break, or you could just love travelling in the fall – and why wouldn’t you? Fall is a perfect time to plan a vacation in Tuscany for lots of people and lots of reasons. You avoid the queues and crowds of the height of summer, the weather remains mild if changeable and the cooler temperatures are conducive to more pleasant exploration of towns and the countryside, prices for many things lower outside of the peak tourist season, and Tuscany’s rolling hills and pastoral scenes are even more lovely when the trees turn an array of gold and red hues. So, if you’ve been dreaming of an autumnal break then we highly recommend Tuscany as a destination and this curation of incredible Tuscany villas with availability over the next couple of months, in particular:

Villa Della Meletta

Villa Della Meletta (available from €293 - €512 per night)


Villa Della Meletta is a truly gorgeous and perfectly located villa in the Tuscan countryside that is 8km from the charming town of Certaldo and within ready access of San Gimignano, Florence, and Siena. Those, therefore, who want a good base from which to make the most of that mild autumn climate in order to explore these gorgeous cities will find that Villa Della Meletta is a perfect fit! However, even if you aren’t going very far throughout your stay, there is plenty to enjoy right at the villa itself; from the pretty and manicured gardens to the luxurious pool area to the bright and inviting interiors of the house. Renovated in 2015, Villa Delle Meletta appears to be a charming and traditional Tuscan stone villa from the exterior but boasts elegant and stylish interiors that have been modernised for your convenience while retaining plenty of local flare and traditional influences. The warm interiors, exposed-beam ceilings, fireplace, bright kitchen, and three cosy bedrooms (sleeping up to eight people in total) are all perfectly designed for sharing meals made with delicious seasonal ingredients from the region, curling up with a good book and some coffee, sitting together to watch spooky films in the living room, and generally enjoying all of the best parts of fall while on holiday in Tuscany

Villa Elly

Villa Elly (available from €540 - €694 per night)


Another very bright and welcoming villa, this gorgeous property is more modern and a more recently built house that features lots of big windows that allow light to stream in (and make the most of as days shorten) and allow guests to admire all of the wonderful surrounding autumnal foliage. Sleeping up to eight in 3 bedrooms, Villa Elly is located just 5km away from San Gimignano, 44km from Siena, and within day trip distance of plenty of other parts of the region, again making it very easy to go and see some of Tuscany’s most beloved towns and attractions during your vacation in the region. Spacious lawns provide ample room for any kids or kids at heart to enjoy the pretty gardens and play various games, while the impressive pool area remains open even through the winter. Many pools close for the colder months as you might see while browsing listings and though the pool at Villa Elly cannot be heated, it can still be used if you have a warm day or are less bothered by the colder water. Inside, Villa Elly features a big, double-height living/dining/kitchen space with a massive fireplace that makes for the perfect room for those holidaying in fall to enjoy cooking, dining, and spending time together in a cosy and welcoming setting. When you are done socialising or going on outings for the day, the simple but relaxing bedrooms are perfect for enjoying some restful sleep and, if you need more help unwinding, then you can check out the sauna room (which is always open and ready to be used without an extra charge or prior notice required). So, if you’re looking for a dreamy setting in which to unwind this fall, Villa Elly surely ticks all of your boxes!

Terrace, Lion Nero

Lion Nero (available from €320 - €565 per night)


Located right in the heart of Florence, this 3-bedroom luxury apartment boasts plush and stylish elegant interiors that beg for fall days of lying around with a hot drink and a good book, views over the city’s iconic Duomo from the terrace (an ideal spot to enjoy the sunset over Florence’s beautiful skyline while drinking a delicious bottle of Tuscan wine, as pictured), and easy access to all of the most famous attractions and sights in the city. If you are looking to make the most of the comparative peace of Florence during the autumn months and want to explore all that the city has to offer without the tourist crowds of the summer, giving you time to see even more – then this is an ideal place to stay! Enjoy the bright and airy interiors decorated with interesting works of art, antiques, and modern touches, the two spacious marble bathrooms with waterfall showers (and the views of gorgeous historic Florence while you brush your teeth), the relaxing and pretty bedrooms, the sleek and modern kitchen, and that astonishing terrace that takes in a panoramic view of the city’s skyline. 

Casa del Colle

Casa del Colle (available from €148 - €210 per night)


A true mountain escape, this pretty little gem of a Tuscan villa is located in the hillside 10km from Viareggio and the coast. Surrounded by trees and with a stone-clad exterior, pretty little wooden shutters, a terracotta roof, a little porch, and several little outdoor seating areas to dine al fresco or enjoy a coffee while breathing in the fresh mountain air, this truly is an idyllic spot for a cosy fall break. Inside, it is just as warm, pretty, welcoming, and picturesque with an open-plan living and dining space featuring a prominent corner fireplace, exposed-beam ceilings, comfortable furnishings, lots of cute little details – such as the decorative plates mounted in a wooden display case on the wall – and the traditional and sweet compact kitchen with its delicately patterned tiles. Upstairs, there is a double bedroom and a twin bedroom, both decorated in charming traditional styles, and there is also a bathroom with a shower in addition to the WC downstairs. Outside, in the garden, there is a little bright and welcoming chalet with a kitchenette and a pull-out bed that allows for an additional two guests to be accommodated at the property. Utterly delightful, like a house from a fairytale or a storybook, this pretty little villa is immersed in nature and a perfect place to escape to during the autumn to get cosy, enjoy beautiful surroundings and walks, spend days exploring Tuscany, and to generally get far away from your daily life and concerns.


So, if you are thinking of planning a fall getaway in Tuscany then we have you covered: from city breaks, to storybook gems in dreamy settings, to perfectly located and spacious houses ideal for spending time together, there are a whole host of perfect and cosy settings for you to choose from!


 Most Popular Holiday Villas In San Gimignano   View more vacation rentals

  Villa Diletta

 Sleeps 5
 Bedrooms 2

  Villa Cafaggiola

 Sleeps 7
 Bedrooms 3

  Casa Andrea

 Sleeps 4
 Bedrooms 2