Villa with private pool on 25 acres in the heart of Chianti, close to Siena Reviews, Deals & Photos 2026

Q: Is Villa with private pool on 25 acres in the heart of Chianti, close to Siena pet-friendly?

Yes, this property allows dogs (limit 1 total). Some restrictions may apply, so please contact the property for more details.

Q: How much is parking at Villa with private pool on 25 acres in the heart of Chianti, close to Siena?

On-site parking is available at the property.

Q: Where is Villa with private pool on 25 acres in the heart of Chianti, close to Siena located?

Situated in a rural location, this villa is within 1 mile (2 km) of Chianti Sculpture Park and La Fornace Art Gallery. Az. Agr.Losi Querciavalle and Castello di Meleto Cantina are also within 9 miles (15 km).

10/10 Excellent

Scott H.

5 May 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Explore Chianti / Tuscany

Excellent location to go exploring the Chianti region! Great old villa well away from everything.

Stayed 14 nights in Apr 2025

10/10 Excellent

Stefanie K.

1 Sept 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Phantastic location in an outstanding Tuscan landscape

We had an outstanding week in an gorgeous estate in the middle of a splendid Tuscan landscape. The house was very tastefully decorated, the climatization was brand new and perfectly working and really nothing was missing and everything was in the best status possible. The whole organisation from checkin to checkout was seemless, the pool temperature perfect.The whole group loved the house and the enviroment.

Stayed 7 nights in Aug 2023

10/10 Excellent

Valerie K., Northern Ireland

27 Sept 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Heaven!

The best hide away. Total sanctuary from today’s world. Our adult family had a wonderful week staying at the house, enjoying the space and peace. It’s hidden away down a very bumpy lane. I suggest no low cars if you are lucky enough to visit. An excellent base from which to explore Tuscany. The property is beautifully restored and very well maintained. It is surrounded by olive and fig trees with its own herd of deer who normally appear late at night to chomp on the grass. If you love being embraced by nature this is the place for you. Thank you to the wonderful (& extremely helpful) owners for sharing.

Stayed 6 nights in Aug 2023

10/10 Excellent

Barth R.

20 May 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet home in the Tuscan Hills

Our family of five stayed here for a week. It was a great place to come back to after day trips to Sienna, Florence, Pisa, Volterra, etc. Super quiet and relaxing. It’s a little bit out of the way, but the extra driving was worth it to us.

Stayed 6 nights in May 2025

10/10 Excellent

Malinda H., Llano, Texas

2 May 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location

We loved our stay here. It was a little challenging to find the first time but so nice and quiet. Everything was as just as described. It was a wonderful experience.

Stayed 5 nights in Apr 2023

10/10 Excellent

Norbert G.

1 Nov 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tuscany at his best

The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend.

Stayed 6 nights in Oct 2023

10/10 Excellent

Jasper T.

11 Jun 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in Tuscany

We were very impressed with Villa Simo. The location was magnificent, with views that we will remember forever. Simonetta was a perfect hostess and always available for contact. The home was perfect for our family group, and we enjoyed cooking and entertaining during our stay. Looking forward to returning someday.

Stayed 5 nights in May 2019

10/10 Excellent

Brent E.

27 Nov 2018

Amazing Tuscan farmhouse

We recently stayed here for a week's holiday. We loved the farmhouse. It had everything we needed for our family of 6. Simonetta was very easy to work with. She answered all of our questions quickly and was at the property to greet us and show us the home. She even cooked us an authentic Italian dinner the first night there. The food and hospitality was like we had never experienced!!!! We plan on visiting again!!!!

Stayed 5 nights in Nov 2018

10/10 Excellent

Camilla L.

19 Apr 2019

Stunning location and great accommodation

The location is faultless and we had fun with many features of the property- the open fire in the living room, the outdoor pizza oven, the olive groves to wander around. It was April so the pool wasn’t quite open but we knew that before booking. Great bedrooms and a fab dining space. We were offered a banquet on the second night (additional cost) and after seeing the menus on offer decided to go with it... it was wonderful- great food and a lovely experience. Overall a great stay- thanks Simonetta

Stayed 6 nights in Apr 2019

10/10 Excellent

Joan P.

20 Jul 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Deciding to spend our summer holiday under the Tuscan sun at Villasimo was the gift that kept on giving. The pictures for this posting on VRBO, while beautiful, do not do this place justice. We have stayed at other homes in the area before, but this one had the perfect mix.Situated between old live trees and Chianti vineyards, with a pool sitting out on a perch overlooking a valley and hills with villages, ancient castles, vineyards - along with absolute peace and exclusivity - this place was amazing. The view from the pool was like being in a live-painting - the clouds even had personality. We enjoyed evenings watching the dusk settle over the valley from the outdoor patio. Balanced with being secluded, the villa is also near towns, a 5-star hotel with a michelin star restaurant next door, and vineyards for winetasting. The road which we jogged could see views of Siena over the vineyards right from the other side of their hill. Last, but certainly not least, the hosts Cristiano and Simonetta were fantastic. The house was in great condition, had everything we needed, a thorough walk through, welcome treats, and were very attentive. They made sure we had privacy and were able to enjoy our weeks in their family home. Would love to stay here again and recommend it.

Stayed 15 nights in Jul 2025

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Jonathan D.

7 Sept 2017

Stunning and remote

This villa is stunning. The view from the pool is breathtaking with Castel Brollio in the distance. It's remoteness is ideal to get away from it all but still only a 20 minute drive from Siena and the Chianti villages. It's very well equipped and spacious. Couldn't fault it in any way. The modern sculpture park in the village is definitely worth a look. We saw deer in the grounds of the villa, fig and olive trees. Absolute paradise

Stayed 7 nights in Aug 2017

10/10 Excellent

Jean M., Pelham, NH

24 Sept 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Rustic Villa in Tuscany

The property was even better than advertised. Location was 20 minutes outside of Siena but in a beautiful rural setting. Home was immaculate and very well appointed for our stay. We had 8 people and we had plenty of room to relax and spread out. Outdoor area was beautiful, pool area was very inviting and a great option when we wanted a day to relax. Scenery was amazing and every room had beautiful view of the Tuscan hills and the beautiful property. We would highly recommend this as a place to stay in Tuscany as it was 45-1 hour away from all the great places to visit in Tuscany: Florence, Siena, San Gimignano, Moltipuciano, and Cortona. Hosts were very welcoming and responsive to questions and communication. We would love to go back now!

Stayed 5 nights in Sep 2019

10/10 Excellent

Matt F.

15 Jul 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful, memorable Tuscan vacation!

Our family of 6 (4 adults and 2 kids) had an incredible time at this property. Clean, spacious well-appointed home with the most stunning panoramic views over the Tuscan hills, and lovely pool area. The hosts warmly welcomed us at check in and had even left us a homemade chocolate cake which was incredible. The home was very clean, each bedroom was very spacious and equipped with AC, and it is very isolated so we appreciated the tranquility and privacy. A car would be a must to stay at this property in our opinion, given the remoteness. Siena was an easy ~20 minute drive and grocery stores/pizzerias/etc are about 15 mins by car. We have to give a special thank you to the host, Cristiano. One person in our group fell quite ill during our week there and not speaking the language, we reached out to Cristiano and he was such an incredible help, I don’t know what we would’ve done without him. He went above and beyond helping us see a doctor and we are so thankful! We had such a fantastic time and would return again in a heartbeat. Thank you Simonetta and Cristiano.

Stayed 7 nights in Jun 2023

10/10 Excellent

Chen T.

20 May 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Tuscan house

We were 3 adults, and we spent 5 lovely days at the Villa. We loved the house and the surroundings very much!We couldn't stop admiring the view from every window and from the yard. The serenity in the mornings was so calming.The house has a good atmosphere, and we liked the design. The kitchen is well equipped.There is a washing machine which we didn't use (no dryer).There is a lovely swimming pool, but we didn't use it either.There are few steps between each 2 rooms in the house, so we wouldn't recommend it for very young kids or elderly people.2 important things to know:- The road from the main road to the house was in VERY poor condition. This could be very challenging for a 'regular'/low rented car. Luckly, we rented a Jeep.We understood this is not the usual condition of the road but one needs to take it into consideration.- Please note there is an additional fee per electricity and gas consumption. This was not a surprise. But take into account this can sum up to a considerable amount. For us, not spending the daytime there (just nights) it was around 250 Euro for 5 nights. The area is also lovely and there is also much you can do without driving too far:Visiting Siena, Wine tasting in one of the many wineries in the area, Visiting 'Parco sculture di Chianti' which we strongly recommend – it's an open park with sculptures integrated in the natural environment.To summarize: The Villa was a great place to spend our Tuscany vacation and we LOVED it!

Stayed 5 nights in May 2025

6/10 Okay

Barbara C.

19 Oct 2025

Liked: Cleanliness, check-in, communication, location

Einrichtung etc alles für bis 10 Personen ausgerichtet, ausreichend und stilvoll.Im Haus aufgrund der kühlen Witterung kalt.(ohne Heizung). Pool deswegen auch nicht benutzt.Anfahrt wie beschrieben „dirty road“, dafür Lage mit Blick auf Castello Brolio . OSO- Lage.250 Endreinigung hohe Stromkosten(auch Poolumwälzung!) Barzahlung, sehr üppig!Staunässe in den Grünanlagen ansonsten waren wir sehr zufrieden auch mit Kommunikation!

Stayed 5 nights in Oct 2025

10/10 Excellent

Raoul H.

4 Sept 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Super Lage, sehr ruhig und sauber. Aber mit SUV sonst wird es spannend um zum Haus gelangen. Pool gros und sauber, alles vorhanden.

Stayed 11 nights in Aug 2025

10/10 Excellent

daniel B.

1 Aug 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magnifique ! Accueil formidable

Un lieu merveilleux au milieu d'une Toscane extraordinaire ! La maison est particulièrement confortable. La wifi un peu faible mais ce n'est pas grave.

Stayed 7 nights in Jul 2024

10/10 Excellent

Brigitte D.

24 Jul 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

In één woord Geweldig

Met gezin van 8 volwassenen een week verbleven in deze geweldige villa. Mooie kamers, een geweldige tuin met heerlijk zwembad! Het ligt wat afgelegen en een half uurtje rijden voor de supermarkt, maar voor ons gezin was dat geen probleem. Pizza’s gebakken in de pizza oven, de keuken was ook ruim voorzien van spullen. Siena is een half uurtje rijden. Aantal wijnhuizen in de buurt bezocht. En ook een aantal keren heerlijk gegeten bij geweldige restaurants in de buurt of iets verder weg. Wij raden deze locatie zeker aan!

Stayed 7 nights in Jul 2024

10/10 Excellent

Harald W.

23 May 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Traumhafter Urlaub in einer wunderbaren Landschaft

Wir waren 5 Personen und hatten einen wundervollen Urlaub in dem abseits gelegenen und sehr gut ausgestatteten Ferienhaus inmitten eines sehr gepflegten Grundstücks. Die Kommunikation mit Simonetta war ausgesprochen freundlich und zuvorkommend. Sie war jederzeit zu erreichen und hat aufgetretene Probleme rasch gelöst. Die Zufahrt zum Haus war zunächst etwas schwierig zu finden und ist für tiefer gelegte Fahrzeuge nicht zu empfehlen. Insgesamt haben wir den Urlaub in diesem Haus sehr genossen und können es guten Gewissens empfehlen.

Stayed 10 nights in Apr 2024

10/10 Excellent

Annick O.

20 Jun 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ferme rénovée avec goût avec vue panoramique sur les collines du Chianti

Séjour très agréable ,chambres confortables et spacieuses , accueil chaleureux des propriétaires, panorama exceptionnel sur les collines du Chianti Nous y retournerons avec plaisir

Stayed 7 nights in Jun 2023

10/10 Excellent

Giovanni Z.

11 Apr 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ottima Struttura

Posto meraviglioso, ottima accoglienza e assistenza. Consigliatissimo

Stayed 5 nights in Apr 2023

10/10 Excellent

Steven C M.

27 Nov 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Under the Tuscan Sun

We loved this 100 year old farm house surrounded by olive trees and wineries. Beautiful views and it was wonderful starting a fire in the huge fireplace. We loved it.

Stayed 6 nights in Nov 2022

10/10 Excellent

Colleen S.

18 Oct 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous views at historical Tuscan property

Great communication and involvement from host. Comfortable, historic farmhouse.

Stayed 7 nights in Sep 2022

10/10 Excellent

Robert M.

5 Oct 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome Villa

Dream vacation in Chianti. 1000 year old farm house with everything we needed. Tuscan hilltop with beautiful views. Our hosts drove from Rome to meet us and showed us everything in the villa to get started. Eight family members were very comfortable. Be prepared to drive 10 -20 minutes for restaurants and groceries.

Stayed 7 nights in Sep 2022

10/10 Excellent

Martin S., Wien

24 Aug 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wunderschönes Haus mitten in der Natur

Wir waren 2 Wochen mit Familie und Freunden in dem Haus und haben die Zeit sehr genossen. Die Eigentümer sind sehr freundlich und hilfsbereit und stehen immer zur Verfügung wenn es Fragen gibt.

Stayed 14 nights in Aug 2022

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

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