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Villas in Chianti - Tuscany

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La Piazza a sleepy hill top village boasts the nearest restaurant and shop within walking distance, 400 meters/yards. The fortifications and covered walkway of Castellina-in-Chianti, 14km/9 miles, bear witness to its many long years at the centre of battles between Florence, 40 minutes, and Siena, 20 minutes; today its primary preoccupations are wine and olive oil. Castellina is situated in the southern part of the Chianti Classico wine-producing region, just off the Chiantigiana road. Hundreds of stone villages as Panzano, Radda and Greve in Chianti, about 15 minutes’ drive away, are sprinkled among these impossibly picturesque hills, many with wonderful restaurants and wine bars tucked into their narrow streets. Florence to the north, to the west San Gimignano and to the south Siena, all about 45 minutes’ drive.

Getting There

Airports nearby:

Airports: Florence, under 1 hour; Pisa, 1 hour 30 minutes.

By Car:

Motorway exit at San Donato, 20 minutes’ drive along paved roads to the property’s gated entrance. Nearest train station at Poggibonsi, 23 Km/14miles. Parking for five cars.

Prices & Live availability

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Rental options (Size of the party):
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NB. are available for parties of different sizes and priced accordingly - select your option above. For smaller parties, the unoccupied rooms or guesthouses simply remain empty or are closed and you will always have exclusive use of the villa and pool.

What's included and not included in your rental charge

Your rental might include some Staff & Services. Our free Concierge can help add-on any extras you require:


  • Weekly rent.
  • Services included (1).
  • Credit card service charges.
  • Hot and cold tap water.
  • Garden and swimming pool maintenance.
  • VAT
  • TN&M Concierge Service
  • 24/7 Emergency Service
  • A weekly cleaning and change of bed linen on Saturdays (2).
  • A weekly change of bath towels on Saturdays (2).
  • A weekly change of swimming towels on Saturdays (2).

Not included

  • Telephone (outgoing phone calls).
  • Flights and car rental.
  • Travel insurance.
  • Transfers to/from airports.
  • Extra services available on request.
  • Use of swimming pool out of season.
  • Tourist tax.

Facilities and utilities

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(1) Please note that, when included in the price, maid service does not include laundry service. If you require any laundry services please advise us prior to your arrival at the villa, payable locally in Euros.

Verified reviews by FEEFO

A live feed of reviews collected independently from our clients by Feefo

service comment
Professional and thorough. Tuscany Now and More made the process of renting the villa in a foreign country simple and I was confident that anything that they would required was asked for and then, that I had completed it well before the trip was underway. Their response time to questions was very prompt and the fact that they reconfirmed all requests with an updated contract was reassuring that all requests were acknowledged. I feel that they are confident that they are using good properties and I got what I saw on the website.
product comment
Our experience at Montesassi was fabulous. It was more than we had even expected. Having Paulo, Alina and Tosca preparing meals and keeping the place clean and tidy was a huge plus. Now that's a vacation! The villa had more places to sit and relax than we could even use. The pool was clean and fresh and the tennis courts added that bit of fun and exercise that a big group needs. The location was nice and central so taking day trips was a matter of 45 minutes to an hour to get to Florence or Sienna or a wonderful winery. Everything was brilliant - we'd love to go back again.
Mrs Donna M Doody
United States
service comment
Great. Lovely choice of villas. Helpful and efficient.
product comment
Beautiful, homely, characterful villa. Pool and tennis court were great. Perfect rural location but easy drive to towns and cities of interest. Lovely views. Paolo, Alaina and Tosca looked after us beautifully. Paolo was so attentive, his food was delicious and he made our stay very special. Thank you!
Mrs Gemma Saunders
United Kingdom
service comment
The service provided by the local staff during our stay (caretaker, cook, cleanup, etc) was exceptional. By the end of our week together, we felt like they were family. They were always timely and gracious. The service provided in making our reservations, arranging for our meals and the directions we received were excellent and very timely.
service comment
The villa was quite old, but had been maintained very well. We became very comfortable, very quickly and just relaxed and enjoyed all of the features of the beautiful home..bedrooms, bathrooms, social areas, pool and tennis court.
Mr Robert C Harrison
United States
product comment
Montesassi was the most wonderful house, with beautiful sitting and dining rooms which we were able to use when the weather was rainy. When the sun was shining, the pool was just the right size and temperature. There were so many places to sit and eat - inside and outside - that we did not use them all and, even after a week, you could still get lost! The staff - Georgia, Paolo and Tosca - were very welcoming and helpful, and cooked delicious meals for us. We thoroughly enjoyed our stay.
Mrs Amanda Sturdee
United Kingdom

These are collected from the feedback forms we send to all our clients.

Great service, quick response time and good information in lead up to our stay. We had the most wonderful week at Montesassi, such a beautiful property in traditional Tuscan style. Multiple indoor and outdoor living and dining areas - lovely to choose different places to sit each day! The pool was loved by the kids in our group and it was lovely to sit by it and admire the views of the surrounding countryside. Lovely bedrooms with views. Great location to explore the towns of Tuscany. Would love to return one day!
Ms Amy Fisk
One of the highlights of our stay at Montesassi was the care and attention from Paulo. Our group was an eclectic mix of Brits, South African, French and Italian including two 6 year old children and two members requiring Halaal food. Nothing was too much trouble for him, the menus were perfect for all of us and he was kind and caring for the whole time we stayed. He would be one of the reasons we would return to Montesassi
Mr John Olsson
South Africa
Our first time booking with you and we loved it. The entire experience was great and it was better than we ever thought it would be.
Mrs Carolyn Lumber
United States
Montesassi, a beautiful vacation and a wonderful spot for friends to gather and visit the hill towns of Chianti. The many living rooms to relax in and the comfortable bedrooms as well as the beautiful grounds and pool just made it a "home" for all of us. The meals and the other services were fantastic. Thank you for sharing your home with all of us. Peter and Heinz
Mrs Victoria Callen
United States
We had a beautiful "Tuscan Experience" at Montesassi! So much beauty in every place we looked! We especially enjoyed the outdoor gathering space. we had beautiful weather but it was too cool for swimming!! We enjoyed the wonderful wines and experiencing Tuscan cooking. Our cooking class was loads of fun too! Georgia took wonderful care of us and we loved the chocolate cake and the fruit tart! <3 Tosca made us zucchini flowers several times as our group loved them. Many thank Tosca!
Mr Robert Dodd
United States
Thank you Paulo, Alina and Manuel for taking care of us and being a such incredible hosts. You made us feel so welcome and the food was absolutely wonderful and some of the best we have ever tasted. Whilst the house, pool, tennis court were real highlights... it was the lovely time here that made our stay so enjoyable. We wish you all the best for the future and thank you all again for our amazing Italian experience.
Mr Kevin Leslie Jones
We asked our family at the end of the week in Tuscany what was the best thing about our holiday: the beautiful views did not make it, the good great local restaurants did not, the beauty of Florence and the hill top tarts were also forgotten. In our party of 9, it was unanimous: Paulo, his welcome and his love of making everyone happy was the best thing about our week - well second to his aubergine parmigiana.... Paulo's culinary skills have been absolutely amazing. No tiny kitchen or cook books, just a love of food, flavours and inspiration. We would eat his food before the fanciest of any Italian restaurant. Paulo, Alina and Manuel have been the best hosts you could wish for and should be cherished. Our business tag line is "great people, great products, great service". Here Paulo and his team have been great people, who have provided us a great holiday with their service and loving attitude. we all wish we could take you home with us. All our love and thanks! The Harpur and Cowlrick families
Mr Brian Harpur
United Kingdom
Our stay at Montesassi was magical. It is a very special place and fulfilled all our expectations
Mrs Hilary Lyle
United Kingdom
To Paola, Alina and Montesassi Team, thank you for a wonderful week! We had a fantastic time staying a Montesassi and exploring Tuscany. The accommodations were perfect - the food was spectacular. Paolo and Alina were above and beyond to make us feel welcome. We will always remember our stay <3 the Davis and the Pohl
Mrs Lisa Davis
United States
What a fabulous vacation we have had here at Montesassi! Your cooking was so delicious and you all contributed to the perfect week in Tuscany. What a wonderful playground this is for us to enjoy and that we did. You all were so helpful trip here. Thank you for your hospitality. We couldn't have enjoyed our vacation more!! (Steve and Donna) Paulo, Aline and Tosca, we leave Italy feeling so fortunate to have been welcomed by you all everyday. Grazie mille!
Mrs Donna M Doody
United States
Paulo, Alina and Tosca in Villa Montessassi, the Heaven!!!! Amazing food, service and hospitality. This place is here away from caos. We enjoyed all the nice mornings with a great breakfast (frittata), what a great star to explore the wonderful villages around here. And after a day of driving in Chianti to the dack here sotting spoiled with a wonderful dinner. What else is better? thank you, thank you (Annamaire), Paulo, ALina and Tosca, Magical experience in Chianti! Could not have ever imagined a better team to spoil us for one entire week. Whatever we asked for they delivered. The frittatas were out of this world. We felt like a family. We will with our friends and family. We will have wonderful memories for a lifetime. XO Dino "Dawg"
Mr Peter Spirk
United States
Amazing memories made in such a beautiful place. Thank you so much Paolo, Alina and Tosca for looking after us so wonderfully. Such delicious food- Polo is a brilliant cook! The villa was fabulous. Relaxing by the pool, playing tennis and exploring wonderful tours and cities. The week went too quickly! We will always treasure such lovely memories and thank Paolo, Alina and Tosca for working so hard to make our holiday so special. Chri, Gemma, Somerset, UK
Mrs Gemma Saunders
United Kingdom
Perfectly located in a beautiful Tuscan countryside with easy access to great local restaurants, small village shopping and both Florence and Siena. A perfect way to experience the quiet, natural life in Tuscany
Mr Robert C Harrison
United States
This villa has been a little bit of heaven for the six of us, just unbelievable and more than we could have imagined! It's been a wonderful family vacation with so much to see and do. We loved the pool, tennis court, large en suite bathrooms and so many places to gather indoors and outside. We were blessed with top care with Giorgia, Tosca e Manuel. The meals were fabulous and Montesassi is so clean and beautiful. This week will remain in our memories forever!! Montesassi exceeded all our expectations and give us an Italian experience we will cherish forever. We felt entirely spoiled the entire time and the food and service were truly spectacular. Thanks for giving us a once-in-a-lifetime vacation!
Mr Robert C Harrison
United States
Thank you so much for the lovely hospitality and wonderful stay in your villa. Tosca and Giorgia were fabulous!
Mrs Elizabeth Mcleman
We spent one week in Montesassi with some freinds. The house is very confortable for 8. Lots of space but would have loved to have less trees in the garden to enable us to have the beautiful view of the valley! Tosca and Paolo were so nice and helpful at every moment and they made our stay a most enjoyable one. Thank you. Grazie mille!! We are going back to Mauritius with wonderful memories of our stay because of you!
Ms Veronique Coombes
This house is very beautiful. The best part of our holiday here though was the incredible people here that made our holiday so special. Paolo is so kind and friendly and helpful. He always makes us feel confortable and happy. Anything we need he helps us with and he is a wonderful person to talk to. Unberto is also very frindly and fun to talk to. His food is delicious. We enjoyed all the food he cooked for us. Tosca is very cute and helpful. We will always remember Paolo, Umberto and Tosca and be grateful to them for making our holiday so special. We loved them. Love from the Kerr family, Australia.
Mrs jaimee kerr
United Kingdom
Beautiful and unique home and setting. We had a fantastic experience taking in the whole Tuscan/Chianti ambience. The house is in peaceful and tranquil surrounds and blissfully quiet! A refreshing experience which allowed us to immerse ourselves in local culture. Thanks to Umberto, Paolo and Tosca.
Mr Damian Gallagher
Totally idyllic! What a privilege to spend two weeks in this beautiful place. Huge thanks to Umberto for such delicious food and to Paolo and madam Tosca for all their hard work. So many happy memories. We hope to come back soon. Grazie mille!
Mrs Sam Underhay
United Kingdom
Our stay at Montesassi has been an enjoyable one. Thank you to the team Umberto, Paolo and Tosca for the lovely food and hospitality. We feel about 5 kg heavier now :-) ! Love the villa and amenities "especially the pool" (said Joel 8). The area and the views are lovely especially the wineries (La Ripa). We will miss Umberto's daily cakes. Thank you from Sean, Tracy, Vivien, Samantha, Joel and Dario.
Ms Tracy Reynolds
We planned this trip for almost a year and Montesassi was everything we hope for… and more! The villa is magical and rich with books and canvas, the courtyard and patios delightful and the pool cool and lovely. We and our five children and parents enjoyed everything so very much. It is also a wonderful home to return to after exploring the generous region of Chianti. Thanks to Giorgia, Paolo and Tosca for our surprising, lovely meals almost each evening and frittata and breakfast every morning. Everyone was so thoughtful and wishing to meet our every need. Grazie mille!
Mr Michael Leggo
United Kingdom
Montesassi - bellissima. La nostra famiglia ha passato una vacanza favolosa qui. Grazie mille a nonna Tosca, Paolo e Tuscany Now.
Mrs Frances Wilmerding
United States
Fabulously comfortable villa in beautiful Tuscan hill country. Cook, gardener, and housekeeper all exceptional. Our family and nanny had a wonderful time and thought the villa very well situated for visiting Tuscany. The pool, the meals, the view, the wine, the staff, all lovely. We highly recommend this villa.
Mrs Frances Wilmerding
United States
Montesassi was the perfect home for our family reunion. We cannot thank you enough for the hospitality and amazing care! The food, beauty, warmth and hospitality was done to perfection in this true Italian farm. I hope all parties in the future can enjoy the home as much as we did! We will definitely be back. Thank you again for a perfect holiday!!
Mrs Susanne L. Principato
United States
We had a grat week at Montesassi, a magical place with jasmine, roses and nightingales. Tosca, Giorgia e Paolo looked after us beautifully - thank you for the vegetarian cooking! Lots of tennis and lazing by the pool and on the terraces. Several trips to Siena, Florence and beautiful tour of an organic vineyard that Francesco organised for us (recommended) and also the restaurant on the castle square (superb). Happy people - great holiday :-) !
Mr Mitchell Dix
United States


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Services available on demand

N.B.: Please note that prices and availability for the following services are subject to change.
  • {{ extra.title }} Maid service available & organised by TN&M concierge service. Cook service available & organised by TN&M concierge service. Shopping list service available & organised by TN&M concierge service. Other services available & organised by TN&M concierge services.

Sample menus can be obtained by contacting Concierge Services

They do request that you pre arrange your meals prior to your arrival by contacting Concierge Services and advise us accordingly.

Remember that if any members have any allergies or food intolerances, you must advise us and of course if you have any personal preferences.

Can we help?

Please let us know your needs and requirements and a member of our experienced sales or concierge team will get back to you immediately.

Call us at +44 207 684 8884

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