Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
5 bedrooms6 bathroomsSleeps 12350 sq m
Popular amenities
Kitchen
Washing machine
Pet-friendly
Gym
Outdoor space
Rooms & beds
5 bedrooms (sleeps 12)
Blue Bedroom
1 Queen Bed
Green Bedroom
1 Queen Bed
Pink Bedroom
1 King Bed
Red Bedroom
2 Single Beds
Yellow Bedroom
2 Single Beds
6 bathrooms
Blue Bathroom
Bidet · Toilet · Shower only · Hair dryer
Gray bathroom on ground floor
Toilet · Shower only
Green Bathroom
Bidet · Toilet · Shower only · Hair dryer
Pink Bathroom
Toilet · Shower only
Red Bathroom
Bidet · Toilet · Shower only · Hair dryer
Yellow Bathroom
Toilet · Shower only · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Garden
Dining area
About this property
Old villa nestled in the hills of Chianti
Villa Il Casolare is a complex of 350 m2. It was built in the 18th century and it dominates the hills of Tuscany. It boasts a breathtaking panorama appreciated in every side of the villa, because it is unobstructed on all four sides. The structure was renovated in January 2014 (with Tuscan style), and combines the love for antique Tuscan décor with the most modern comfort and luxury: every detail is intended for the pleasure and relaxation of the client. The structure, consisting of a main house, an attached house, and a private swimming pool immersed in nature, is located on a hill in a dominating position. It is surrounded 360° by a park of one hectare decorated with cypress trees, fruit trees, olives, and vines. It is located a few kilometres away from Certaldo. This is a privileged location for those who desire relaxing and calm holidays and want to visit the most beautiful city of art in Tuscany.
Main House Ground floor: access through three different entrances, spacious hallway, reading room/library, living room with fireplace and TV, dining room, independent kitchen with fireplace, small bathroom, and cellar with a selection of wines and oils.
First floor: TV room, 5 bedrooms with en-suite bathroom Red Suite: bedroom with king size bed, built in wardrobe, desk, and bathroom with shower. Yellow Room: bedroom with two single beds, wardrobe, chest of drawers, armchair, and bathroom with shower. Green Suite: bedroom with two single beds, wardrobe, and bathroom with shower. Blue Suite: bedroom with king size bed, wardrobe, desk, armchair, and bathroom with shower. Pink Suite: bedroom with king size bed, wardrobe, chest of drawers, and bathroom with shower.
The living room on the first floor is accessed via a magnificent 'Colombaio' staircase that rises along the structure and offers a splendid panoramic view of the Chianti Classico hills.
Attached House The veranda in front of the house leads to a typical Tuscan barn, in which there is a spacious living room with fireplace and a fully equipped gym, all surrounded by large windows that assure exceptional brightness and a view of the surroundings. Veranda: attached to the barn, it is a lovely porch with wide arches and offers a breath taking view of the surrounding hills. It is equipped with a large dining table to enjoy fantastic outdoor dining moments.
Swimming pool It is nestled a few steps away from the house. The pool measures 14 x 7 m. The surrounding solarium is built from handmade bricks typical of the region. It is completed with sun beds, beach chairs, chairs, and umbrellas.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Pet-friendly
Gym
Outdoor space
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
Gambassi Terme
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
Events allowed: family gatherings, birthday parties, weddings
default
Pets
Pets allowed: limit 2 total
100,00E small/mid dogs
(25kg)
200,00E big size
default
Smoking
Smoking allowed: in designated areas
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, birthday parties and weddings) are allowed on site. Maximum attendees: 30
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 and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Certaldo
Located in Certaldo, this villa is in a rural area. The area's natural beauty can be seen at Castelvecchio Natural Reserve and Rocca of Montestaffoli, while Vine and Wine Museum and Benozzo Gozzoli Museum are cultural highlights. Il Fiaschetto and Chianti Observatory are also worth visiting. Fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and hiking/biking trails nearby.
Church of Saint Jacob and Saint Philip - 12 min drive - 7.5 km
Palazzo Pretorio - 12 min drive - 7.5 km
Museum of Sacred Art - 12 min drive - 7.5 km
Tenuta Torciano Winery - 17 min drive - 12.8 km
Getting around
Certaldo Station - 12 min drive
Peretola Airport (FLR) - 71 min drive
Restaurants
Castello’s Jazz Bar - 12 min drive
Bar Cavallino - 13 min drive
Osteria A Casa Tua - 15 min drive
C'era Una Volta - 10 min drive
La Taverna del Fiorentino - 13 min drive
Frequently asked questions
Does Old villa nestled in the hills of Chianti have a pool?
Yes, this property has a pool.
How much does it cost to stay at Old villa nestled in the hills of Chianti?
As of 9 April 2026, prices found for a 1-night stay for 2 adults at Old villa nestled in the hills of Chianti on 6 June 2026 start from NZ$1,552, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Old villa nestled in the hills of Chianti pet-friendly?
Yes, this property allows pets (limit 2 total).
How much is parking at Old villa nestled in the hills of Chianti?
On-site parking is available at the property.
What time is check-in at Old villa nestled in the hills of Chianti?
Check-in begins at 4:00 PM.
What time is check-out at Old villa nestled in the hills of Chianti?
Checkout is at 11:00 AM.
Where is Old villa nestled in the hills of Chianti located?
Situated in a rural location, this villa is within 6 miles (10 km) of Palazzo Pretorio, Church of Saint Jacob and Saint Philip and Casa del Boccaccio. Castle of Oliveto and Vine and Wine Museum are also within 9 miles (15 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Great accommodations and wonderful hosts. Certaldo was a pleasant surprise and a central location for our Tuscany adventures. Owners were very helpful with house specifics and arranging for serveral amazing restaurants. Saluti!
Danny M.
Stayed 9 nights in Sep 2025
Response from VrboOwner on 3 October 2025
Thank you very much Danny for your kind message about our house. We are very happy that you enjoy the house and the surrounding area!
We had the most beautiful time. Perfectly located. Loved the views, loved the bedrooms and private bathrooms, loved the kitchen and all the kitchen supplies. Highly recommended. Thank you!!
We spent a lovely week in this beautiful property. Eleonara and Andrea are amazing hosts. I would most certainly recommend them and we would definitely go back.
This was the perfect property for me and our family. It is spacious, well appointed, and in a wonderful setting. Our hosts were also easy to deal with, communicative and just really good people. I highly recommend the villa!!
William V.
Stayed 8 nights in Sep 2022
Response from VrboOwner on 11 October 2022
Thank you so much William for your kind words and review.
I'm very happy that you enjoy your time in our villa and have a quality time with the family.
It was a pleasure have you all here!
Best wishes for the future,
Eleonora
We loved everything about this property, inside and out. Great house, beautiful grounds and views, and a large, family-friendly swimming pool. Our party covered 3 generations and we all had a thoroughly enjoyable time. A special mention to the hosts, Andrea and Eleonora, too, who couldn’t have been more welcoming or helpful - whether it was recommending a restaurant for lunch or a pizzeria that did great takeaway. We had a truly excellent time in a very beautiful house.
Nigel P.
Stayed 7 nights in May 2025
Response from VrboOwner on 5 June 2025
Dear Nigel,
thank you very much for your review.
We are happy that you and your family enjoy the house, the place and the service.
Hoping to have you again here, we send our greetings.
A fantastic place to stay. Spacious, quiet and with all imaginable comfort. Eleonora has been a wonderful hostess during our stay, always available for advice and we can definitely recommend her meals. No downside to this place whatsoever.
Hans C.
Stayed 7 nights in Jul 2020
Response from VrboOwner on 22 July 2021
Thank you Hans for your kind words and for have choose our villa for your family holidays. It was a pleasure have you all here!
Greetings from Villa il Casolare!
Great villa with 5 large rooms, each with its own full bathroom. Large common room and kitchen - great for getting all guests together. Place it 10 min by car from downtown Certaldo, and great for a base for exploring Toscana (we did Florence, Siena, Val d'Orcia, San Gimignano, Volterra) on day trips.
Sydney C.
Stayed 8 nights in Dec 2023
Response from VrboOwner on 15 January 2024
Thank you Sydney for you review, we are happy that you have a nice time in our villa.
Our multigenerational family had a wonderful stay. Elenora and her mother made us a delicious dinner upon our arrival (I would highly recommend taking her up on this offer). The house was comfortable and well equipped. It was well located to explore so much of what Tuscany has to offer including an easy ride to Firenze.
Gillian G.
Stayed 5 nights in Feb 2023
Response from VrboOwner on 27 February 2023
Goodevening Gillian, thank you very much for your review. We are happy that you all enjoy your stay in our Villa.
Best regards!
The renting went very smoothly. Eleanora was very helpful and professional. Villa was fantastic and in a beautiful location - quiet but I’m reasonable distance of Certaldo town.
Peter B.
Stayed 7 nights in May 2022
Response from VrboOwner on 9 June 2022
Thank you Peter for your review. It was a pleasuere have you and your friend group at our Villa.
Thank you so much, Eleonora
A group of college friends and spouses spent two weeks in this amazing villa. It was fantastic! The Villa is beautiful, well equipped, and able to fit a large group easily. We enjoyed the pool every day. Eleanora was wonderful to communicate with. Definitely worth a stay. And the location is fantastic for day trips.
Heather s.
Stayed 13 nights in Sep 2023
Response from VrboOwner on 9 October 2023
Thank you very much Heather, we are very happy that you have a nice stay at Villa il Casolare, it was a pleasure have you here!
Our three generation family had a lovely one week stay at Villa Il Casolare. There was something for everyone - wonderful clean and safe pool for the children, shade patios for grandma and a very workable kitchen for our volunteer chef. Our hosts went out of their way to be accommodating and helpful. We would highly recommend this villa for others doing a family gathering.
Kathryn Z.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 7 September 2022
Thank you very much Kathryn for your review.
It was great have your big family here in our house!
Grazie mille,
Eleonora
We were a group of 8 from Canada and had a fantastic stay !! The villa was gorgeous! We were so lucky to be able to watch the process of picking and processing the olive oil!! Eleanora and her father were so hospitable and helpful with all of our questions! We also had a dinner made for us one evening and highly recommend that also!!
Thank you Eleanora and your family for the wonderful stay!!!
Cathy W.
Stayed 5 nights in Nov 2022
Response from VrboOwner on 2 December 2022
Dear Cathy, we are very happy that you enjoy your stay here. Your group was fantastic, it was a pleasure have you in the period of new olive oil!
We wishing you all the best for the future!
Eleonora
The perfect setting for a perfect vacation with amazing friends of 60 + years!..The pictures of this beautiful home do not portray the exquisite decor and furnishings of each room..The views are breathtaking and Eleonora is so sweet and personable..A pleasure to speak with and so helpful! Our stay was a dream come true for each one of us!
Linda L.
Stayed 5 nights in Oct 2023
Response from VrboOwner on 23 October 2023
Thank you very much for stay in our villa. We are very happy that you enjoy your time here, it was a pleasure meet you all! Greetings, Eleonora
We had a wonderful week in the house. We all appreciated the spacious areas, the kitchen and the pool, perfect for relaxing and family dinners in the patio. We were 8 adults and 2 children, and all bedrooms and bathrooms were very clean and comfortable. Eleonora was very helpful with everything we needed help with and also arranged a very nice dinner for us in the house.
Christina F.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 3 July 2023
Christina, thank you very much for your review, it was a pleasure have your family here in our villa.
Thank you and greetings!
Many thanks Eleonora and Andrea for making it possible for us to stay and enjoy your beautiful Villa il Casolare!
It was a magical experience for 7 Australians who fell in love with the Villa, it’s location, Old Town Certaldo and all the amazing Medieval towns and cities we explored.
The Villa was so comfortable, spacious and beautifully appointed and the pool was a huge plus.
We had so much fun and look forward to returning in the future.
We highly recommend Villa il Casolare, Certaldo as we loved our stay.❤️🐶
Verified traveller
Stayed 5 nights in Oct 2022
Response from VrboOwner on 18 October 2022
Thank you so much Debbie for your kind review. It was a pleasure have help you for enjoy your Tuscany holiday. Truly happy that you like our house and all the area.
Wishing at your fantastic family all the best for the future!
Staying in this listing with my family was an absolute delight. The Villa is massive, super well equipped (each bedroom has its own bathroom & shower!!), and keeps its cool indoors on hot summer days. The views of tuscan hills during breakfast or during sunset are postcard perfect. We were not missing anything and wished we could stay longer!
Eleonora was a wonderful host, super communicative and always ready to help. It's the perfect spot for a vacation to disconnect from busy city life. Can only recommend.
Mouhammad Z.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 30 July 2024
Thank you very much for your review, we are very happy that you enjoy the house and your family holiday here.
Thank you for your stay and be such a nice family! Greetings to all!
Our group of six enjoyed a week long stay in this villa and it was wonderful. The villa is stunning as are the grounds and surrounding countryside. We were able to easily take day trips to Florence, Siena, San Gimignano, Volterra, and the Chiantigiana road from this location. Our host Eleonora was exceptional. She was more than accommodating, had great suggestions on activities for our group, and helped us extensively during our stay. Eleonora and her mother also prepared two evening meals for our group that were just outstanding. A real welcome to Tuscany. We strongly recommend this property.
Mo & Shelly R.
Stayed 7 nights in Oct 2024
Response from VrboOwner on 10 October 2024
Thank you very much Mourice for your review. It was a pleasure have you and your kind friends at the villa! Best regards to all of you!
The villa is beautiful. Exactly as one would envision on the perfect trip to Tuscany. It is fully restored and new. A comfortable home for the week in the hills near Certaldo.
Eleonora was great and very helpful with information about the area. We thoroughly enjoyed. One caution for future guests is that we were charged for diesel for hot water. A minor complaint but should be included in the rental price.
john j d.
Stayed 6 nights in Jun 2024
Response from VrboOwner on 25 June 2024
Thank you John for your review about us, we are glad that you enjoy our villa.
For sure we will work for make easier all the conditions of renting.
Thank you
Staying at this beautiful house in Tuscany was beautiful. From the stunning views of the rolling hills to the charming rustic interiors, every aspect of our stay exceeded our expectations. The house was immaculately clean, well-maintained, and equipped with all the amenities we needed for a comfortable stay.
The location of the house was perfect for exploring the enchanting towns and vineyards of Tuscany, allowing us to immerse ourselves in the rich culture and history of the region.
Overall, our stay at this house in Tuscany was nice. Highly recommended for anyone seeking a perfect blend of comfort and authentic Tuscan charm.
Michael L.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 2 April 2024
Thank you Michael for your review. We are really happy that you enjoy your stay in our villa.
Owners were easy to deal with very accommodating! Villa was spacious each room had its own bathrooms, the grounds & views from the villa were amazing. Unfortunately we had mostly rain but there were many places to sit outside & to enjoy the views. The pool was nice but did not use it.
They take recycling serious which we liked.
Long flight of stairs up to the bedrooms a bit hard to bring up heavy luggage. Would definitely rent it again!!
Susan B.
Stayed 6 nights in May 2023
Response from VrboOwner on 19 May 2023
Thank you so much Susan for your review! It was a pleasure have your group here for Italy holidays!
We had 4 couples 55-64 age, and family that stayed a week. Eleonora a was a fabulous post. Communication throughout the process was great. The night we arrived, we had Eleonora make a meal for us for my wife’s 60 b-day. It was a feast and wonderful. Everything at the villa surpassed our expectations. The views from the back patio of the Elsa valley and San Gimignano were like a post card. Can’t say enough great things about this place. We certainly hope to cone back
Dennis D.
Stayed 7 nights in May 2023
Response from VrboOwner on 26 May 2023
Thank you very much Dennis for your review, we are very happy that you have good memories and good times in our villa!
Simply amazing. Everything about this experience surpassed our expectations.
First, the property itself is stunning. Pictures hardly do justice. The home is also extremely comfortable and came fully equipped with everything we needed for a fun and relaxed stay.
Second, the town of Certaldo - 10 min drive away- is fantastic! It has excellent restaurants, an old medieval area and is far less crowded compared to neighbouring towns like Sienna.
Last but not least, Eleonora is simply wonderful. She went above and beyond to make us feel at home.
Shaheen M.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 19 July 2023
Thank you very much Shaheen for your review. I'm very happy that your wonderful family have a nice time and good memories here in our villa. Thank you to your for your kindness. Wishing to you all only the best!
This was our first family trip to Italy and the villa made it special. This property is huge and views even better than in the pictures. It could easily accommodate two families. The pool is very clean and a huge added bonus for days you want to stay at the villa. Kitchen is functional and well suited for large meals.
There’s a small town about 15 minutes drives away with a pizzeria and two excellent restaurants. You can also travel to Certaldo where’s there’s a grocery store and a lot of restaurants in the old town. Overall, it is very well located if you want to travel the Chianti region.
The only thing I would caution is the mosquitos if you’re not from a tropical area. They are everywhere in the area and I’d highly recommend getting bug spray.
Kaelan C.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 26 June 2023
Thank you very much for your review! We are happy that you enjoy our house for the Tuscan Holiday!