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STUNNING VILLA with a private pool in the heart of Chianti

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A table set for a meal in a rustic stone building with a brick archway, surrounded by greenery.
A rustic kitchen with exposed brick walls, a wooden ceiling, and a stone staircase leading to an upper level.
A pool with lounge chairs and a stone wall.
A living room with a sofa, coffee table, and bookshelf. There is a brick archway leading to a dining area with a table and chairs.
A stone building with a gravel driveway and a garden with purple flowers.

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms6 bathroomsSleeps 137535 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
castelnuovo berardenga
  • Place, Castello di Meleto Cantina
    ‪11 min drive‬
  • Place, PoggioBrandani
    ‪11 min drive‬
  • Place, Meleto Castle
    ‪13 min drive‬

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About the neighborhood

Castelnuovo Berardenga

Located in Castelnuovo Berardenga, this villa is within a 15-minute drive of Chianti Sculpture Park and Castle of Brolio. .This villa is 10.2 mi (16.4 km) from Piazza del Campo and 5.9 mi (9.6 km) from Az. Agr.Losi Querciavalle.
View more Villas in Castelnuovo BerardengaOpens in a new window

What's nearby

  • Castello di Meleto Cantina - 11 min drive - 8.7 miles
  • PoggioBrandani - 11 min drive - 8.7 miles
  • Gaiole in Chianti Stadium - 12 min drive - 10.0 miles
  • Meleto Castle - 13 min drive - 9.3 miles
  • Castle of Brolio - 15 min drive - 10.2 miles

Getting around

  • Rapolano Terme Station - 34 min drive
  • Florence Airport, Peretola (FLR) - 97 min drive

Restaurants

  • ‪Hotel Executive - ‬21 min drive
  • ‪Agribar - ‬11 min drive
  • ‪Dievole Wine Resort - ‬18 min drive
  • ‪Bar Pasticceria Scacciapensieri - ‬21 min drive
  • ‪Pizzeria Osteria Bella Napoli - ‬15 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

STUNNING VILLA with a private pool in the heart of Chianti

Beauty. Peace. Hospitality. An experience for those who wish to nourish their minds. Along the banks of the Arbia River—immortalized in Dante’s works—stands Villa Il Cerretaccio, nestled deep within the enchanting landscape of the rolling hills of the Sienese Chianti region, designated an UNESCO World Heritage Site.
The villa, perfectly restored, is characterized by its 13th-century watchtower, which dominates this part of the valley. Two side structures were added to the tower to house the guards of the ancient Castle of Cerreto, the ruins of which are open to visitors not far from the house.
Surrounding the villa is a 27-hectare estate featuring olive groves, vineyards, and woods, offering a feast of colors and fragrances for your enjoyment. Villa il Cerretaccio is the ideal starting point for all your car trips or hikes to discover the wonders the area has to offer.
The most interesting parts of the Classic Chianti region are located within 15 kilometers of Villa Gaiole, including Castellina and the Castle of Brolio. The greatest attraction is undoubtedly the city of Siena, rich in art and culture, just 12 kilometers from the villa along scenic roads that follow the gentle contours of the hills.
And if you just want to do nothing, you can relax with a dip in the pool, a yoga class in the shade of the trees, or a friendly chat with the owner.
Please note that any trash left at the villa after check-out will incur a €120 disposal fee.



HEATING IS NOT INCLUDED.
Make yourself comfortable in this air-conditioned villa, which features a fireplace and a private pool. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a desk and a microwave, and housekeeping is provided on request.
Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool.
Breakfast is available for a fee.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach loungers

Pool/Spa

  • Massage
  • Outdoor pool
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Dining

  • Breakfast available for a fee
  • Chef service
  • Dining table

Bedrooms

  • 7 bedrooms
  • Bedsheets provided

Bathroom

  • 6 bathrooms
  • Bidet
  • Hair dryer
  • Shower
  • Shower/bathtub combination
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Stereo

Outdoor areas

  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • One pet total (up to 55 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Housekeeping (on request)
  • Unit size: 7,535 square feet

Policies

Check-in

Check-in time starts at 5:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load the dishwasher
Remove leftover food and drinks and take out the trash
Turn off the lights
Failure to complete these may result in a negative review from the host.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
1 total (up to 55 lbs per pet)

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings and birthday parties

Smoking

Smoking is not permitted

Important information

You need to know

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
Parties and events (including family gatherings and birthday parties) are allowed on site; maximum attendees: 13
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number IT052006B5L7GH7FGW

We should mention

All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed EUR 5000, due to national regulations; for further details, please contact the property using information in the booking confirmation

STUNNING VILLA with a private pool in the heart of Chianti Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 29 out of 31 reviews
Rating 8 - Good. 1 out of 31 reviews
Rating 6 - Okay. 1 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

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

Family holiday

Great villa great view fantastic hostage
Stayed 6 nights in Jun 2025
Verified review

10/10 Excellent

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

Amazing villa in the heart of Chianti

We were a group of 4 families with toddlers and loved our stay at the villa! Alessandro was an excellent host and very responsive. The views and pool are stunning, and the house is clean and decently equipped. Highly recommended for a group stay in Chianti!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing property in one of the most scenic parts of Tuscany! Alessandro and his family were great hosts who are very attentive and responsive. The home chef dinners were a highlight of our trip. Would highly recommend. Thank you!
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

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

This was the best place for our family vacation!

We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host!
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed for a week at this lovely villa and thoroughly enjoyed it. With 12 people (3 families of 4), we very comfortably each had our own space plus many spots inside and out to spend time together. Alessandro was a gracious and responsive host. His parents were equally welcoming and we made the smart choice to have his mother cook a delicious dinner for us which presented the quintessential al fresco experience. So glad we stayed here!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The kids loved the old villa, it had a bit of a rambling castle feel to it. It could do with a few new items. Tv, sound system and cookware all a little past their use by date but that's not why you are really there anyway.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

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

Amazing villa!!

There were 12 of us that stayed at this beautiful villa! A beautiful spot!!! The house was very clean and Alessandro was there to greet us as well as very helpful in answering any questions and very prompt in responding to us when we had questions. My only suggestion - be sure you grab toilet paper and paper towels for your stay - we didn't realize the house wouldn't have those items. A wonderful, wonderful stay - you won't be sorry if you rent this beautiful villa!!
Stayed 4 nights in Oct 2023
Archival

10/10 Excellent

Beautiful Tuscan Villa not to be missed!

Beautiful villa and guest quarters in a remote Tuscan city surrounded by vineyards and olive trees and spectacular views in every direction. The hosts are most cordial and invite you to a tour and tasting of their shared winery. The countryside is so magnificent. If you are looking for a peaceful and quiet oasis, try this lovely villa which will accommodate your whole family and assorted friends. Enjoy afternoons basking in the Tuscan sun by the large pool while tasting wines from surrounding vineyards!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved our stay at the Villa! Our family of 11 including teenagers, adults and seniors all felt very at home and all felt that we had more than enough space for privacy if we needed it from one another!:). It was so clean and the fact that it was such an old property was so impressive and made the stay there so much better. The pool was absolutely perfect! The different eating options outside made it so nice depending on the time of day. The communication with the host and the hospitality we received was top notch! We were so sad for our holiday to come to an end and will always recommend this villa to anyone who is vacationing in the Tuscany area.
Stayed 9 nights in Jul 2025
Verified review

10/10 Excellent

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

BEAUTIFUL 13th Century Tuscan Villa

There were 8 of us on my 60th Birthday trip. We were fortunate enough to stay in this BEAUTIFUL Tuscan Villa built in the 13th century. SO much history here. It used to be a convent. We did day trips to Siena and Florence(twice) The villa is centrally located to many vineyards. We took a day trip to 3 vineyards and had lunch at Brunello di Montalcino. Very fun! We had a pizza dinna catered at the Villa one night. There are a bunch of bedrooms and the 4 we used were very comfortable and had modern amenities. The host was exceptional. We absolutely LOVED our stay and hope to be back!!!
Stayed 5 nights in Apr 2025
Verified review

10/10 Excellent

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

Family and friend

We rented the villa after a family event. The owners and their son are very charming and accommodating. We enjoyed the villa as it is very authentic. Felt like we were locals. It has separate areas almost like apartments within the villa which is great if you have many couples. One of the rooms has bunk beds and the other two twin beds. It’s important to know you can’t walk anywhere so a car is needed. That’s the only reason for my location rating. Excellent villa to spend time with friends and family.
Stayed 6 nights in Sep 2024
Verified review

10/10 Excellent

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

A great family trip to Tuscany

The house is lovely and Alesandro and his parents do a great job of making everything run smoothly. The back patio is really the place to hang out and we had many a family dinner back there. The location is smack in the middle of picturesque Tuscany and you will be hard pressed not to enjoy the views. I would definitely organize a night where they cook a meal for you… lovely food. My only real wish was that the mattresses on the beds were a little more comfortable. Most were pretty hard and in need of an upgrade or some kind of a topper. For family trips… great fun though. The kids loved living in a 12th century country home with a pool. Enjoy folks.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

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

Ultimate Tuscan Villa Experience

The villa is absolutely stunning. The 5 suites, within one villa, are all connected and spacious. There is plenty of room for everyone to have their own space or to come together. The pool, gardens and road are well maintained. There is a gate at the top of the driveway entrance. Alessandro was available for any questions and lives in the Anex about 100 years away. So, there is someone on-site if issues arise. However, privacy is abundant. When our group is 8 stayed st the villa, there was a cleaning crew that came in every two days. The villa is perfectly situated between Siena, Florence, Cortona, etc. Alessandro suggested visiting the tiny walled city of San Gusme. We found this tiny city to be quite charming and nice break from the crowds of the bigger cities. You can walk the entire city in 10 minutes. It includes a Michelin rated restaurant. I would highly recommend this villa for anyone looking for a spacious luxury experience in Tuscany. We’ll be back!
Stayed 5 nights in Sep 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nothing to add
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great centrally located villa, very clean, near all major locations in Tuscany. It was very hot during our stay with all children and grandchildren, and the AC and pool helped to cool off. Grandkids want to come back next year for my 91st birthday. They can talk to Alessandro, our wonderful host who attended to all our requests.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

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

Bellissima struttura immersa nel verde

Villa molto bella e proprietari disponibili. Eravamo un gruppo di 12 amici, abbiamo vissuto la struttura in piena comodità. Disponibilità di barbecue a legna e saloni muniti di camino estremamente conviviali.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Exceptional

Everything about the Villa was perfect for a large group. Everyone had there own bedroom and bathroom. The place had several large gathering spots which were perfect for our group to enjoy at the end of the day. The location was ideal for day trips to all the areas we wanted to visit, including Florence, Siena & San Gimignano. Pino, Betty and Alessandro could not have been better hosts and more welcoming of any needs.
Stayed 4 nights in Nov 2022
Verified review

10/10 Excellent

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

Gray time

We had the best time. Pink and his wife were wonderful hosts. The dinners were delicious and each room was very clean.
Stayed 4 nights in Nov 2022
Verified review

10/10 Excellent

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

Beautiful stay in Tuscany!

Our group of four couples had a wonderful stay at this amazing villa. Alessandro and his parents were wonderful hosts from from start to finish. The villa was gorgeous and the scenery was like living in a postcard. We enjoyed cooking together after our days of sightseeing and wine tasting. Four two evenings, we had arranged for Alessandro’s parents to cook for us, and it was a wonderful experience to enjoy local home cooking outside on the covered patio. Pinot and Betty were so friendly; we left with new friends! I think it is helpful to understand that the drive to Siena or the major hilltop cities is 30 or more minutes on windy, hilly roads, and there is some gravel. Just be aware that it is part of the charm of being in the beautiful quiet countryside! We are so thankful we chose this experience!
Stayed 5 nights in Oct 2022
Verified review

8/10 Good

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

Family and Friends trip to Italy

We had a wonderful time in the country side of Tuscany / Chianti region. The Villa was very spacious for everyone to have their own space. Lots of steps and wings of the house. Kinda tricky with young children. Beds, pillows and linens could be updated. Alex the owner was very helpful and arranged several things for us. Great option for large group. Sleeps 10 comfortably. You definitely need to have a car or driver to get you around the area.
Stayed 5 nights in Sep 2022
Verified review

10/10 Excellent

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

Gorgeous villa in the heart of Tuscany!

We recently returned from a week-long stay in this gorgeous villa. We had a group of 10 adults and 4 children, and the villa had ample bedrooms and space for all. Six of the seven bedrooms have A/C and were well-cooled in the midst of an oppressive heat wave in Italy (one bedroom did not have A/C). Despite the rest of the house not having central A/C, most of the villa stayed remarkably cool and comfortable during the day. The kitchen was well-supplied with a full-size fridge as well as a mini fridge - plenty of pots, pans, plates, glasses, utensils made it easy and fun to prepare our own meals in the villa. We also enjoyed one of the upstairs dens for family gatherings in the evening (the den also has a small kitchen attached with another mini fridge). The outdoor spaces were gorgeous and well maintained. The pool was very clean and a highlight for all at the end of hot days sightseeing! There are two outdoor dining areas that are perfect for morning coffee and evening cocktails & meals. Alessandro and his parents, Pino and Elisabetta, live on site and are very welcoming. Alessandro was exceptionally helpful and responsive in answering questions before and during our trip. He worked with me ahead of the trip to schedule a wonderful dinner prepared at the villa by Elisabetta, including delicious wine produced by their family. He provided several suggestions for places to visit nearby and also helped us plan and book a full-day minibus excursion to Montepulciano and Pienza, including a wonderful winery tour at Poliziano. (I also recommend a stop at Vallepicciola winery, just a three minute drive from the house - stunning building / views and more delicious wines). Alessandro and his parents also went above and beyond as hosts when one of our party had a medical emergency. They were extremely gracious and supportive in helping us navigate through that issue, for which I will always be grateful.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Amazing Tuscan villa , divided to two seperate houses. Perfect for families.

Beautifull area. Equiped with all you need . Spacious. Lovely gardens and surroundings. Allesandro , the owner is really attentive, all our wishes were fullfilled, the family also makes great wine. Bottom line - the ultimate Italian Tuscan experience for families or large group .... been there for 7 nights , felt like home , will be back!
Stayed 7 nights in Sep 2018
Verified review

10/10 Excellent

Quintessential Tuscan experience

We had a wonderful stay at the beautiful home of Alessandro and Pino who were both lovely hosts. We were a big group, consisting of 4 families, but there was plenty of space to spread out between the main house and the annex (each contains 5 bedrooms). The villa is situated in the heart of Tuscany, close to Siena and various exceptional wineries in the area (Castello di Ama is a particular highlight not to be missed). I wish we could have stayed longer!
Stayed 7 nights in Aug 2018
Verified review

10/10 Excellent

Lovely tuscan retreat

Just got back from a week at this wonderful little piece of Tuscan paradise. Set in the middle of vineyards and out of the way from the summer bustle of Siena and Florence, the Il Cerretaccio villa is a great place to relax and slow down. We scored perfect weather, as expected in July, and the manager Alessandro was always available to make sure that our questions and needs were met. Highlights: - Pool: the water temp was perfect, the pool was super clean and we spent a lot of time there, surrounded by nature and colorful landscaping. - Alfresco dining: take advantage of the solid kitchen and make some great family meals to be enjoyed in one of the two outdoor dining rooms with panoramic vineyard views. - A/C: This is one of the few rentals in the region that offers A/C in most rooms, which was very welcome! - Alessandro: The manager was always around to answer questions and help out with directions. His family makes *stellar* wine, and we purchased about a case of his family Chianti which was outstanding. - Location: the nearest town is 10-15 mins away, so you are on your own. Day trips are pretty far (Siena is about 30 mins away), so consider spending full days at the home and full days sightseeing, you probably can't do both in one day. Hickups: - Internet is really slow and since the villa has solid stone walls, don't expect internet connectivity throughout the property or even in specific spots. It makes sense, you are in the middle of the vineyards on vacation. But if you are hoping to get some work done, it's not really going to work. - The drive: the directions to the villa on the HomeAway app are just wrong, and took us for a ride all over southern Tuscany. Not sure I am supposed to disclose the exact location of the villa on HomeAway in a review, but it's really easy to get good directions on Google Maps if you just enter the name of the villa directly. - The villa is actually separated into 2 different buildings, something that is not stated clearly in the house description. The two buildings are about 100 yards apart, so not under the same roof even. Something to obviously consider! - Critters: you are in the middle of the countryside, so unexpected visitors might show up from time to time. Overall, we would return in a hurry. The place is great and truly exemplifies old farmhouse Tuscan living.
Stayed 7 nights in Jun 2018
Archival

10/10 Excellent

Fantastic place!

This villa is amazing! Beautiful surroundings, pool and great rooms. 100% recomended!
Stayed 4 nights in Sep 2017