While lots of our villas are best enjoyed during the warmer months – our villas with pools in Tuscany, in particular – it is often true that many listings have something to offer in every season. The properties located in lush settings that feature views over the famous rolling hills and forests of Tuscany are especially lovely in the autumn as they treat guests to panoramas that change colours with the season. These are villas that received 5-star reviews from guests this fall and that are ideal whether you are coming when the spring first blooms, the sun is bright in the sky, the leaves begin to fall, or when it’s time to curl up by the fire...
Papiano, Casentino Valley
5 bedrooms
2 bathrooms
Sleeps up to 12
This charming stone villa in Tuscany boasts sweeping views over the lush Casentino Valley, dreamy traditional interiors with lovely original features, a fenced-off swimming pool with an outdoor shower and ample loungers with parasols, a playground, and several picturesque areas to dine al fresco. Divided into two apartments, it is ideal for a group looking to get away together but still have some personal space.
“I spent a weekend with 11 friends at Villa Renaccio. The villa is in a splendid location, offering an incredible view, and there are several nature trails for walking nearby. The apartments are cozy, clean, and equipped with everything you might need. The owners are extremely kind and helpful; I highly recommend this place.”
Francesca C.
Milano (Italia)
3 bedrooms
2 bathrooms
Sleeps up to 6
Framed by olive groves, this is another lovely stone villa with swimming pool in Tuscany that boasts picturesque and lush surroundings as well as wonderful spaces in which to enjoy those views in the gardens while lounging by the pool, dining, or simply sitting out and taking it all in. Paired with the traditional interiors and you have a perfect Tuscan getaway!
“We had a fantastic holiday in an outstanding property. Full marks for this delightful place, where we lacked nothing; for the excellent preparation and support provided by the agency; and for the incredibly kind hosts on-site, who look after their property with great care while remaining wonderfully discreet. Anyone seeking absolute peace and relaxation will certainly find it here. Thank you so much for such a wonderful time—we would love to come back!”
Margot S.
Grevenbroich (De)
Asciano, Orcia Valley
2 bedrooms
1 bathroom
Sleeps up to 4
A cosy and very pretty stone cottage located on a historic estate in the famously lovely Orcia Valley, Pieve di Sant Ippolito boasts shared access to a gorgeous kidney-shaped pool with a hot-tub built into one corner, lovely and perfectly manicured grounds, and bright and welcoming interiors that have wonderful original features. The owners live in a historic manor house on the estate and there is also a renowned church on the grounds that dates back to the 3rd-4th century and is home to a fresco by celebrated artists of the Umbrian School.
“Linda gave us a very warm welcome upon our arrival and gave us a tour of their magnificent home. It’s a true little paradise with no shortage of amenities designed for our comfort. Throughout our week-long stay, Linda was always there for us and attentive to our needs—checking to see if we were doing well and offering advice on places to visit. We have wonderful memories of that week—we were truly pampered. And if fate allows, on our next getaway to Tuscany, we’ll return to Linda’s place without hesitation. It’ll be a heartwarming reunion.”
Pascal M.
Langrolay sur Rance (Fr)
Castagnori
6 bedrooms
6 bathrooms
Sleeps up to 14
Exceptionally romantic, this beautiful and historic luxury villa in Tuscany combines elegant and modern décor with stunning interiors that boast incredible original features such as stone walls and exposed beam ceilings. Named for the adjacent church that adds a lovely tower to the skyline, the building overlooks lush scenery and is surrounded by well-tended grounds that boast a beautiful infinity pool, an area to lounge under a plant-draped pergola, a panoramic terrace with a large table and parasol for elegant meals al fresco, and more. Stylish and tasteful, with amazing amenities and four hours of cleaning included per week, and surrounded by trees and hills, this gem is the perfect spot for a luxury escape in the Tuscan countryside.
“We spent a relaxing week at this superbly appointed holiday home, which is situated in a quiet location. The house is tastefully and comfortably furnished. We would like to come back.”
Fabienne Marielle R.
Hautpwil (Switzerland)
So, if you are looking for perfect rentals that suit no matter when you want to travel, then discover some of the gems that earned 5-star reviews this autumn, even after the excitement and heat of the summer had faded away for 2026. Make the most of Tuscany’s beautiful properties, traditional and cosy interiors, and stunning leafy views no matter the time of the year by booking with Tuscany Villas!