Apartment vacation rentals in Province of Siena

A fantastic apartment in the most beautiful location. Enrichetta was always very quick to respond, flexible and very attentive. We were personally greeted at check-in by Ian who always ensured we had everything we needed throughout our stay. The view from the apartment and the pool is truly breathtaking. I definitely recommend staying here! We hope to return again in the future.

Check and confirm the location with the owner before traveling

We had a wonderful family vacation in this secluded olive grove. Starting every day with a refreshing dip in the pool was our absolute favorite ritual. The area is suitable for easy and medium hikes. Our hosts were exceptionally friendly and helpful.

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.

We thoroughly enjoyed our stay at Massimo's place in San Gimignano!!! We couldn't have asked for a better location in the town. We spent three wonderful days there and we will cherish the memories we made. Massimo was so nice and his wine bar was perfect. If we're ever lucky enough to come back to San Gimignano then we will definitely stay here again. It fit six of us comfortably. Thank you for the excellent service, Massimo!!!

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.

A lovely property with an incredible view! We had a wonderful week there, thanks to Marta for being so helpful and responsive. Highly recommend!

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

The entire property was absolutely wonderful – from the location to the overall living experience, everything exceeded my expectations. The host was incredibly welcoming and kind, showing great care and hospitality from check-in to check-out. I truly felt at home during my stay. On my arrival, the host thoughtfully gifted me a bottle of wine, plenty of fresh fruits, and some delicious chocolate pastries – such a warm and generous gesture that made me feel instantly comfortable. The house itself is very spacious, bright, and beautifully decorated, with a cozy and inviting atmosphere. Every morning, I would wake up feeling refreshed and grateful, as sunlight poured into the rooms – it was simply beautiful. I genuinely loved my time here, and whether for a short stay or a longer visit, this place is absolutely perfect. Highly recommended to anyone visiting the area!

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!

Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!