Condo holiday rentals in Province of Siena

We had a great stay at this apartment! The location is absolutely amazing—right in the center, walking distance to everything. The flat itself is very well equipped with everything we needed for a comfortable stay. A special mention to the host who was incredibly helpful, even arranging an emergency dentist appointment for us—truly above and beyond! The apartment comes with valet parking, which was convenient, although you do need to walk about 6 minutes to the meeting point to retrieve your car. Just a couple of things to keep in mind: if you arrive after 10pm, there’s an extra fee, and with luggage, it’s best to take a taxi to be dropped directly at the apartment, as only taxis are allowed access inside the area. Overall, a wonderful experience and would definitely recommend it!

Absolutely beautiful apartment in a fabulous location. We loved being in the rooftops of beautiful Siena. Apartment had everything you needed. The restaurant opposite (about 2 metres away!) is also fantastic and worth a visit The lift is from about 8 steps up so just note that if that is very important to you. We got a taxi from the station where we parked our rental car for 2 euros a day. Was really worth staying in the centre. We loved it.

My daughter and I stayed 3 nights in early June in this wonderful home. It was spacious and clean, and very comfortable. The host was very clear in her instructions. The location was fantastic! It was an easy walk to the Duomo cathedral, Piazza del Campo, and pretty much everything in the city center. We really enjoyed sitting at the kitchen table, enjoying the breeze, and looking out the window at the historic buildings and the top of the cathedral in the distance. Thank you for a memorable stay! We can’t wait to come back…

Gorgeous space, with incredible views. Convenient located on a quite street, close to everything you need.

Nora’s apartment is simple wonderful. Located just a stone’s throw outside the Siena old city wall, the location is perfectly quiet but walkable to the entire town, and affords much more space than average. This is a very large one bedroom, with plenty of lounge space, plus an actual washer plus separate dryer! The bed was super comfortable and the Nespresso machine was lovely. Nora was a fantastic host, helping answer questions before arrival and during the trip. Would definitely stay here again on our next trip to Siena.

This place is great, I strongly recommend it. The hosts are also amazing. We stayed while doing a bike trip around Tuscany and the hosts allowed us to store our bikes in their garage.

A super nice place to stay. The way there is a bit adventurous and not recommended for low-riding vehicles, but otherwise quite doable if you drive slowly. But it is also totally quiet there. The cottage is nicely furnished. Everything important was available and Alessandro even greeted us with a bottle of wine. The bed and pillows are extremely comfortable. The squeaky gas boiler and the fact that the water temperature in the shower fluctuated quite a bit are a bit annoying. Maybe it can still be repaired. But that's already whining at a high level. All in all, a great accommodation with a very nice and accommodating host.

This was the most amazing apartment right in the middle of everything! Literally just behind the Piazza del Campo we walked out our door and had everything right there. And the apartment was so cool! Everywhere you look there’s cool features. It was so unique and charming. We loved having the windows open to the view of a restaurant below and the rolling hills beyond. Fabio was very helpful as well. We would definitely stay here again.

Such a beautiful, peaceful place to spend a few days! It was central to many tours and activities, great for exploring! Luca was a wonderful host and ensured we were happy and had everything we needed. The restaurant was great! I can’t think of anything that would have made our stay better! Completely exceeded our expectations!

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.

Benedetta’s place was perfect! Just what my family of 4 needed for a quick trip to Montepulciano. Would definitely recommend staying here!

We had a wonderful time at Alberto‘s and Laura‘s - it turned out that we didn’t do as many trips into the surroundings as planned because we just wanted to enjoy the beauty of the garden and the amazing views. It was the perfect ending of a fantastic vacation in Italy - I hope we will be back next year :) We received a fantastic welcome, home made bread, jam and pasta - and immediately felt like home. Grazie! One thing to mention is that the apartment is kind of thin-walled towards the second apartment - that didn’t bother us at all, but might be of interest for fellow travellers who are sensitive to noises. All in all, certainly one of the best accommodations we have stayed in!

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

The apartment is conveniently located, but far enough from town centre to be quiet and peaceful. Barbara made extra effort with leaving milk and a few drinks, enough toilet paper, and other basics like olive oil which was helpful. We loved the small balcony looking out on a green space and found the beds comfortable and apartment clean.

Lovely apartment in the historic centre of San Gimignano, excellent level of cleanliness. Well-equipped kitchen, comfortable bed. I stayed for two nights and had a great time. The hosts, Federico and Helga, are fantastic and very friendly people. Excellent tips on how to get around the area and on restaurants with typical Tuscan cuisine and places with views of the hills ideal for aperitifs at sunset. I would definitely go back!

Very comfortable accommodations and gorgeous property and views

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 👌

Pierre, Eric and family have created an amazing place to stay. From the warm welcome on arrival and dinner with them the next night, a week was not enough time spent there. They have really created a beautiful place to stay and we look forward to staying again.

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!

We really enjoyed our stay! Emanuele and Angela were very kind and replied to any question very quickly. The place is perfect to relax and take day-trips to nearby towns such as Cortona, Pienza, Montalcino and Montepulciano. We enjoyed the pool after big days of visiting the surroundings during very hot days. I recommend it to anyone who wants a mix of visiting and relaxing! :)

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.

The stay at Raisa's was incredibly beautiful. The accommodation and especially the view is much nicer than in the pictures. Raisa has gone to great lengths to make everything as pleasant as possible for us. The dogs (Saila and Yango) are mega cuddly, the pool is great and the entire property is really picturesque. Beautiful city trips etc. are easily doable by car and we would be happy to come back again sometime.

Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!