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

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

A stone building with a tiled roof, a swimming pool, and a garden with various plants and trees.
Property video
A table set outdoors with a view of a stone building and a grassy landscape.
A cozy living room with a wooden ceiling, a fireplace, a red sofa, and a wooden coffee table.
A bedroom with a large bed, wooden headboard, bedside tables with lamps, a mirror, and a window with a view of greenery.

Reviews

9.8 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
5 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Private pool
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Pievasciata, Tuscany
  • Place, Chianti Sculpture Park
    ‪4 min drive‬
  • Place, La Fornace Art Gallery
    ‪5 min drive‬
  • Place, Piazza del Campo
    ‪33 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed

Bedroom 4

2 Single Beds

Bedroom 5

2 Single Beds

Bedroom 5

1 Double Bed

3 bathrooms

Bathroom 1

Bidet · Toilet · Shower only

Bathroom 2

Bidet · Toilet · Shower only

Bathroom 3

Bidet · Toilet · Shower only

Spaces

Kitchen
Garden
Dining area

About this property

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

Welcome to Villa Simo!
Our stone farmhouse sits on a hillside in Chianti, just 15 km from the center of Siena. We invite our guests to relax in the garden, take a walk on our 25 acres of private woods, and take in the view of the Chianti hills from the private pool.
Villa Simo sleeps 10 people in 5 comfortable, spacious bedrooms with exposed wooden beam ceilings and terracotta floors. All the 5 bedrooms have AC.

The pool is for your exclusive use.
Villa Simo has 5 bedrooms, 3 bathrooms, 1 living room, 1 dining room and 1 fully equipped kitchen.

You can make your own pizza and use the working wood burning oven next to the barbecue!
Villa Simo is perfect for families and groups of friends who want to spend a relaxing holiday immersed in a tranquil and peaceful environment.
Unlimited internet WiFi available.

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Property grounds
Secluded villa between Chianti vineyards, private pool, tennis, large garden
Gaiole In Chianti
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (46 reviews)
Secluded villa between Chianti vineyards, private pool, tennis, large garden

House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 1 total)
Only if agreed at the moment of the reservation
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Smoking

Smoking is not permitted
Smoking is only allowed outside

Check-out instructions

The host requires you to complete the following before checking out:
Start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and return the keys
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property Registration Number IT052006C2D8PUWWDW
Property # 6256561
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Castelnuovo Berardenga

Located in Castelnuovo Berardenga, this villa is in a rural area. Chianti Sculpture Park and Palazzo Comunale are cultural highlights, and some of the area's attractions include Frateria di Padre Eligio and Siena Circuit. Looking to enjoy an event or a game while in town? See what's happening at Gaiole in Chianti Stadium or Siena Stadium. Take some time off to enjoy the winery tours in the area, or get some fresh air with adventures like cycling nearby.
View more Villas in Castelnuovo BerardengaOpens in a new window
Map
Pievasciata, Tuscany

What's nearby

  • Chianti Sculpture Park - 4 min drive - 2.2 km
  • La Fornace Art Gallery - 5 min drive - 2.6 km
  • Banca Monte dei Paschi di Siena - 30 min drive - 15.0 km
  • Piazza del Campo - 33 min drive - 16.1 km
  • Siena Cathedral - 35 min drive - 15.4 km

Getting around

  • Rapolano Terme Station - 34 min drive
  • Peretola Airport (FLR) - 98 min drive

Restaurants

  • ‪Pizzeria Ristorante Camping Colleverde - ‬18 min drive
  • ‪Hotel Executive - ‬19 min drive
  • ‪Agribar - ‬19 min drive
  • ‪La Botte Del Chianti - ‬11 min drive
  • ‪Dievole Wine Resort - ‬17 min drive

Frequently asked questions

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

Yes, this property has a pool.

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.

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.

What time is check-in at Villa with private pool on 25 acres in the heart of Chianti, close to Siena?

Check-in begins at 3:00 PM.

What time is check-out at Villa with private pool on 25 acres in the heart of Chianti, close to Siena?

Checkout is at 10:00 AM.

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 1.1 mi (1.8 km) from Chianti Sculpture Park and within 6 miles (10 km) of Borgo Scopeto e Caparzo Srl and Fattoria della Aiola Winery. Az. Agr.Losi Querciavalle and Basilica dell'Osservanza are also within 9 miles (15 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 70 out of 80 reviews
Rating 8 - Good. 9 out of 80 reviews
Rating 6 - Okay. 1 out of 80 reviews
Rating 4 - Poor. 0 out of 80 reviews
Rating 2 - Terrible. 0 out of 80 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Jessica K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house and surroundings are amazing, we had a wonderful stay and the hosts were great and so easy to communicate with.
Stayed 11 nights in May 2026
Verified review

10/10 Excellent

Scott H.

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
Response from VrboOwner on 18 May, 2025
Thank you so much for your kind words! We’re truly delighted that you enjoyed your stay at our country house. Knowing that you appreciated the peace, nature, and atmosphere makes us very happy. We sincerely hope to host you again soon for another relaxing getaway. See you soon!!
Verified review

10/10 Excellent

Barth R.

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
Response from VrboOwner on 22 May, 2025
Thank you so much for the wonderful review! We're absolutely delighted that you enjoyed our countryside home and that your stay met your expectations. It makes us very happy to know you appreciated the peace and the connection with nature. We hope to welcome you back again very soon!
Verified review

10/10 Excellent

Malinda H.

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
Response from VrboOwner on 3 May, 2023
Thank you!
Verified review

10/10 Excellent

Norbert G.

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
Verified review

10/10 Excellent

Brent E.

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
Response from VrboOwner on 26 Mar, 2020
Thanks for your comments!
Verified review

10/10 Excellent

Stefanie K.

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
Verified review

10/10 Excellent

Camilla L.

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
Response from VrboOwner on 26 Mar, 2020
Thank you Camilla, it was great to have you and your family here. We look forward to having you here again.
Archival

10/10 Excellent

Jonathan D.

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
Response from VrboOwner on 26 Mar, 2020
Thank you, we hope to have you here again!
Verified review

10/10 Excellent

Valerie K.

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
Verified review

10/10 Excellent

Jean M.

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
Response from VrboOwner on 26 Mar, 2020
Thank you for pointing out all the beautiful characteristics of our house, it makes us happy to know that you enjoyed your holiday at Villa Simo. We hope to have you back in the near future.
Verified review

10/10 Excellent

Joan P.

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
Verified review

10/10 Excellent

Matt F.

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
Verified review

10/10 Excellent

Chen T.

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
Verified review

10/10 Excellent

Mika F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Die Unterkunft ist der Hammer. Perfekte Balance zwischen Ruhe und nicht zu abgelegen. Die Ausstattung war super für 10 Leute!Unfassbar schöne Aussicht und Charme.Wir kommen super gerne wieder!
Stayed 6 nights in Jun 2026
Verified review

10/10 Excellent

Greg H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location, quiet and serene . The dinner the host prepared for us when we arrived was excellent .
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

Michel J.

Liked: Cleanliness, check-in, communication, listing accuracy
This villa is deep in the Chianti valley with rustic charm and tranquility. We had difficulty finding the place as we did not follow the instructions provided by the host but it was clear after a quick phone call. We were created with a generous authentic Tuscan meal and wines which were very welcome after a long trip. The place is cozy, antique for sure has all the amenities for a comfortable stay. It is designed to keep the indoors cool it hot summer days so it was a bit chilly during our.visit.late April early may. We used the outdoor cooking area with some degree of success... It would be helping to have a supplier of ready made wood for the fireplace or pizza oven. The farm roads were fantastic to Run or bike and the Vallepicciola vineyards was fantastique! I would return in a heart beat!
Stayed 6 nights in Apr 2026
Verified review

6/10 Okay

Barbara C.

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
Verified review

10/10 Excellent

Raoul H.

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
Verified review

10/10 Excellent

daniel B.

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
Verified review

10/10 Excellent

Brigitte D.

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
Verified review

10/10 Excellent

Harald W.

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
Verified review

10/10 Excellent

Annick O.

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
Verified review

10/10 Excellent

Giovanni Z.

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

Ottima Struttura

Posto meraviglioso, ottima accoglienza e assistenza. Consigliatissimo
Stayed 5 nights in Apr 2023
Response from VrboOwner on 13 Apr, 2023
Grazie, è stato un vero piacere ospitarvi
Verified review

10/10 Excellent

Steven C M.

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

About the host

Hosted by Simonetta

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Languages:

English, German, Italian

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