See all properties
Entire home

Old villa nestled in the hills of Chianti

Photo gallery for Old villa nestled in the hills of Chianti

Pool
Property grounds
Exterior
Exterior
Exterior

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms6 bathroomsSleeps 123767.4 sq ft

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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Pet-friendly
Gym
Outdoor space

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Pool
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
10.0 out of 10, Exceptional, (46 reviews)
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano

House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

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 the information in the booking confirmation
A car is required for transport to and from this property

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 Teatro del Popolo are cultural highlights. Il Fiaschetto and The SottoVico Garden 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.
View more Villas in CertaldoOpens in a new window
Map
Certaldo, Toscana

What's nearby

  • Casa del Boccaccio - 12 min drive - 7.5 km
  • 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

  • ‪Bar Caffetteria Boccaccio - ‬15 min drive
  • ‪C'era Una Volta - ‬10 min drive
  • ‪Pizzeria Boccaccio - ‬12 min drive
  • ‪Il Castello - ‬12 min drive
  • ‪Taverna L'Antica Fonte - ‬12 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 6 Mar 2026, prices found for a 1-night stay for 2 adults at Old villa nestled in the hills of Chianti on 8 Mar 2026 start from £522, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 58 out of 60 reviews
Rating 8 - Good. 2 out of 60 reviews
Rating 6 - Okay. 0 out of 60 reviews
Rating 4 - Poor. 0 out of 60 reviews
Rating 2 - Terrible. 0 out of 60 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Danny M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 9 nights in Sep 2025

10/10 Excellent

Norma B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 6 nights in Oct 2025

10/10 Excellent

Suman C.

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

Beautiful stay in Certaldo

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.
Stayed 7 nights in Jun 2025

10/10 Excellent

Nigel P.

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

A Tuscan retreat

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.
Stayed 7 nights in May 2025

10/10 Excellent

William V., Rochester, NY

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

Great Family Property

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!!
Stayed 8 nights in Sep 2022

10/10 Excellent

Karolina A.

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

Tuscan dream

Lovely house in an even more lovely landscape. Would highly recommend.
Stayed 5 nights in Mar 2024

10/10 Excellent

Hans C.

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

A splendid holiday

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.
Stayed 7 nights in Jul 2020

8/10 Good

Sydney C.

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

Very good stay close to Certaldo

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.
Stayed 8 nights in Dec 2023

10/10 Excellent

Gillian G.

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

Great stay in Chianti

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.
Stayed 5 nights in Feb 2023

10/10 Excellent

Peter B.

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

Villa rental

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.
Stayed 7 nights in May 2022

10/10 Excellent

Tim W.

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

Fabulous week in heaven

The property was exactly as described, and Eleonora a perfect hostess. Beautiful view, amazing pool. Very relaxing. Highly recommended.
Stayed 7 nights in May 2022

10/10 Excellent

Heather s.

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

Amazing time in Tuscany

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.
Stayed 13 nights in Sep 2023

10/10 Excellent

Kathryn Z., White Rock, British Columbia, Canada

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

Intergenerational Vacation

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.
Stayed 7 nights in Jul 2022

10/10 Excellent

Cathy W.

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

Outstanding stay!!!

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!!!
Stayed 5 nights in Nov 2022

10/10 Excellent

Linda L.

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

Memories with lifelong friends at Il Casolare

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!
Stayed 5 nights in Oct 2023

10/10 Excellent

Christina F.

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

Three-generation get-together in Tuscany

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.
Stayed 7 nights in Jun 2023

10/10 Excellent

Verified traveller

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

Totally stunning!

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.❤️🐶
Stayed 5 nights in Oct 2022

10/10 Excellent

Mouhammad Z.

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

True Tuscan Experience

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.
Stayed 7 nights in Jul 2024

10/10 Excellent

Mo & Shelly R.

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

Wonderful villa in Tuscany

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.
Stayed 7 nights in Oct 2024

10/10 Excellent

john j d.

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

Beautiful Villa in the Hills near Certaldo

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.
Stayed 6 nights in Jun 2024

10/10 Excellent

Michael L.

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

Beautiful House

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.
Stayed 7 nights in Mar 2024

10/10 Excellent

Susan B., Martha's Vineyard, MA

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

Better place to stay then what the photos show

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!!
Stayed 6 nights in May 2023

10/10 Excellent

Dennis D.

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

Party of 8 adults

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
Stayed 7 nights in May 2023

10/10 Excellent

Shaheen M.

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

FANTASTIC. If you find it, book it!!

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.
Stayed 7 nights in Jul 2023

10/10 Excellent

Kaelan C.

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

Amazing stay in picturesque Tuscan countryside.

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.
Stayed 7 nights in Jun 2023

About the host

Hosted by Eleonora Casini

Host profile image

Languages:

English, Italian
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals