Holiday rentals with a pool in Province of Siena

What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!

"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!

We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.

Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.

Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!

We had a wonderful time in this absolutely cute house, which is surrounded by breathtaking nature. The tranquility is unique – you can only hear the chirping of the birds, and every now and then deer appear at the edge of the forest. Simply magical! The pool was well maintained and you had real peace. A real highlight for us was the kitchen: so lovingly furnished and exceptionally well equipped - we have never experienced anything like it! The gas stove and the high-quality oven have made cooking a pleasure. Host Diego was incredibly friendly, attentive and warm. You immediately feel welcome and well cared for. A perfect retreat for those who appreciate nature, tranquility and loving details.

Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

Had an amazing time with Sara & Simone - truly the best hosts we've come across. The place was fantastic, amazing views by the pool, great room, clean and all the amenities needed are available. Sara & Simone are great hosts, they made us breakfast one day which was amazing, fresh organic food with the best view. And all their local recommendations and reservations made our trip in Tuscany much nicer. Can't wait to come back again 👌

We stayed in Monica’s home for five nights and four days, and it was incredible. The second we checked in Monica sent me an extensive list of instructions and places to visit during our stay. My favorite list was restaurants and local food shops in the area she recommends as a local. The house had all the amenities you could need/want, comfortable beds, and a really nice patio area. We are a few meals outside and enjoyed the stunning view. We saw some of the most beautiful sunsets as well. The pool was really well kept. There were many wineries the were nearby. The location was also great for taking day trips to Florence and Siena. The nearest town was so cute and had a lot of nice shops and restaurants. We are so appreciative of Monica’s food recommendations and suggestions of things to do. Overall we had an amazing time, and we highly recommend staying here!!

A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended

I stayed at this place for 4 nights with my partner at the beginning of June 2025. It was so homely, very tidy and clean, with lots of amenities and the host was very welcoming. The views were incredible. We had a car which made visiting other places super convenient. We definitely recommend and would love to come back one day!

Francesco is an excellent host. Podere Cupiano is a fantastic estate. The views are to die for. Sopratutto, the pool is amazing. Montieri is a super cute and friendly town nearby with great restaurants. You should also visit the restaurant at VIN Hotel, a ten minute walk away.

We can absolutely recommend it! Everything is as described in the text and can be seen in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information for the journey and many great tips on site, always with the corresponding links. For example, our arrival was delayed due to traffic to around 10:15 pm. Was no problem, we were in contact and when we arrived, Andrea personally welcomed us. And if we had a question during our stay, an answer always came very quickly. (Where is the best place to park in Siena, how do you get to Florence, ...)

We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Our stay at Podere Vignali was amazing. Our hosts were friendly and generous and nothing was too much trouble. It was private and beautiful and felt like a home away from home.

Very lovely house with pool at the beautiful countryside

Pierluigi and his wife have built a beautiful home in the San Gimignano hills. We had a perfect week with our family there. The house and gardens have gorgeous views over the vineyards and olive groves, and we woke to bird song every morning. The place is spotlessly clean and felt like a home away from home, with all the amenities you could need. The town is a short drive away and is stunning, with great restaurants and things to see and do. The road leading to the villa is rough and steep, however it is worth it for the peace, quiet, privacy and views. Pierluigi and his wife welcomed us in person and they are the loveliest people. He was helpful and responsive throughout our stay via text. We will return!

We had a great stay at the villa! Diego and Aldo were great hosts and were very responsive to any issues we had. There was a slight issue with the water but both of them were able to quickly help and were extremely kind. Would definitely recommend!

Fabio’s house was absolutely wonderful! Janine was super helpful, and the place was so clean and comfortable. It fit our 2 large families easily! Thank you for letting us stay and relax and take in the gorgeous countryside!

We had a great time in the house. The view is amazing, a lot of nature, nice and fresh pool, big terrace and garden, lots of bird and other animal sounds, no neighbors. The rooms were quite big and the kitchen very well stuffed. There is also a washing machine, dish washer and 2 big fridges. A few small points we feel like we’d like to mention from our side however: - one of us was trying to work from abroad and the WiFi was quite bad. it was not strong enough for a zoom call, so home office is not really doable from there - some (2/5) bathrooms had a really bad smell. We couldn’t really find out where it came from - some of the showers were not really water proof. The water went basically out of the shower into the bathroom - quite some ants in the kitchen, but with some effort (insect spray and avoiding foods on the counter) it was possible to keep them out We still had a great time. It is the perfect place to disconnect and we would definitely come back! Thanks a lot!

Overall the location and charm of the property were stunning. Spacious bedrooms and living areas (beware uneven flooring, to be expected in an old farmhouse, my elderly father struggled). NOTE: we have not been asked for a cash deposit with Airbnb before and were surprised when a man came about 3 hours after we arrived to collect €400 cash. He spoke no English and used his phone to call someone who could speak to me. The host had not said he would be coming, or who he was. I contacted Airbnb support who said I could pay through the resolution centre. As others mentioned, there were no oil, salt, pepper etc, although a few dishwasher tablets. The jacuzzi and sauna work with tokens for €8 each. Didn’t use so not sure how long you get. BUT, this is a stunning property with unbeatable views in the heart of Tuscany, tucked away on a hillside down a gravel track. Would definitely book again. Pool is pristine, towels spotless, beds comfortable.