Apartment vacation rentals in Province of Siena

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We enjoyed staying in this luxurious apartment. Even though we stayed only one night it was spoiling and we had a beautiful views!

We had a wonderful stay with Marco, Mauro and Lucia as a young family. The apartment is beautifully located in nature in a small village in the Chianti area. It was very quiet, surrounded by vineyards and forest. The tennis court is a great addition, the swimming pool was still closed for the stay (early April; but it would have been too cold) By car, it is a perfect starting point to get to know the Chianti area, be it the towns and villages, the wine, the cuisine or the history.

Very beautiful apartment ! Spacious for 7 adults

A breathtaking stay & an accommodating host!

We visited from California after traveling throughout Europe for 2 weeks. We were pretty sick of rubbing shoulders with other tourists. Our stay at this residence completely recharged us. The staff is wonderful, the pool is so nice (especially in this heat), delicious dinner, and all is in a secluded, magical location. The spa was a real treat at the end. Never experienced something like this before, it was amazing. Totally a five star experience.

We loved our time at L’Assolata! It’s a beautiful spot, within close driving distance to many towns in Tuscany such as Pienza, Siena, Sarteano, and Montepulciano. It’s a bit farther away from Lucca, Volterra, and San Gimignano - so just plan for longer drives if your itinerary includes these places. It’s a serene place to both relax and explore. The views are INCREDIBLE! Even though the weather was cold and rainy a lot during our time there, we had a nice day sitting by the pool and it was the best! It’s just down the hill from the village of Radicofani. We loved walking around there and going to the bakeries and butcher shops. The cottage is clean, beautifully decorated, and just as described. Sara was very helpful! We had the best time and hope to return again someday!

Had a beautiful time staying at this spot as our home base as we travelled into Siena and around Tuscany for a few days. Enrico and his family were very nice and the property is beautiful! It was particularly helpful to have laundry use to wash some things to get through the end of the trip.

We had a great time. The accommodation is very nice, with all the essentials including breakfast and very close to the center. Chiara was very kind and helpful in recommending places to visit and restaurants to eat. I highly recommend it

Fabulous place! The view was amazing, great location and it had everything we needed. It was easy to find and close to everything. A great stay!

Place is great..... Waking up in the morning and enjoying that view is priceless. There was everything in the house, especially in the kitchen. I think it is strategically located 20/30 from all the main attractions in the area.

Enjoyed our stay at Jacopo's very much! Easy day trip to Val d'Orcia.

We had a really good time in a comfortable house and a stone's throw from Albus Alpacas !

We stayed with Sonia and Roberto for two days on the occasion of New Year's Eve 2025. Before our arrival, they were kind enough to make sure we didn't have any food allergies to prepare a welcome kit and left us their phone numbers for any reason. Upon arrival, we had difficulty finding the accommodation and they were so kind as to meet us on the street. In addition, they have always been responsive, flexible and provided us with all the necessary information about transportation and taxis. Roberto was so kind as to personally accompany us to the station on our departure. The place is very tidy and clean, but a bit far from the center if you want to walk around (35 minutes). It is well served by public transport, available until about 8:30 pm.

Great location in the town center, great host, always fast to respond. The house was nice & warm, hot water was easy to control and the house was well equipped. Overall we enjoyed our short stay in San Gimignano.

Great family run place! Welcomed and greeted by Robert’s mother with a glass of wine that Robert made himself. Robert’s mom doesn’t speak any English but she was just so sweet and welcoming. The view is gorgeous and this place is a true agritiursimo with active vineyard and olive farms. Highly recommend.

Marta’s Red Rose apartment offers stunning panoramic views that highlight the beauty of Tuscany. Every morning, we woke up to this enchanting landscape, and every evening, we wound down with it, making our two-week stay feel truly magical. The apartment is compact but efficiently designed, providing a comfortable and well-planned space. We had everything we needed throughout our stay. The farm, with its blend of rustic charm and modern touches, added to the overall experience and made for a pleasant environment.

Definitely one of the best homes ever rented so far. Very spacious bathroom and very spacious shower. The bathtub is a little bit

Mario, Anna and Claudia are such a wonderful family and lovely hosts . They want to make sure you have the best stay ever. The beauty of this property and Siena itself is one you see in paintings . I was so sad to leave after 3 nights I asked if we could extend because I wish we booked longer ! Everything is breathtaking. This is the best booking we have made in our 13 years of marriage. You will not be disappointed. I am already planning our next trip back and thinking of renting the entire villa for that trip! Thank you for the best stay !!

Our stay at Villa di Geggiano was truly magnificent! It is difficult to put into words how very special and magical our experience was in the Alfieri Suite at the Villa but I can say that, without a doubt, this was our absolute favorite Airbnb experience ever! The entire property, outside grounds, the incredible views,the beautiful Alfieri Suite we stayed in,the luxury amenities and especially Andrea,our exceptional,very gracious host at Villa di Geggiano all contributed to make this an unforgettable experience that we will treasure for a lifetime. If you have the incredibly good fortune to find this little slice of heaven available for your dates,please,I urge you not to hesitate…book this immediately,I promise you will not regret it. The suite we stayed in had every conceivable amenity you could ever need and more. It was beautifully and so tastefully decorated and we truly felt completely at home there for our 4 night stay. We give Andrea & the Villa our highest recommendation!

Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!

We loved our stay in Gianluca’s apartment. Gianluca is a fantastic host and was very responsive and accommodating to all our queries. The apartment is stylish, spacious, spotlessly clean and equipped with everything needed for a comfortable stay. We loved that this apartment has its own private spa with jacuzzi and steam room. The apartment is well located, in the heart of the town, and just a few minutes walk from the bus station. We would highly recommend staying here when visiting Siena.

Love love love Montepulciano and Monica’s place is an ideal location to experience the area. The apartment was cozy, clean and has beautiful views! Love this stay!

Nice place near Tuscany, good recommendation from host. Own Villa but in shared space. Thanks!