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Villas in Chianti - Tuscany

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The fortifications and covered walkway of Castellina-in-Chianti, 3.5km/2 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 are sprinkled among these impossibly picturesque hills, many with wonderful restaurants and wine bars tucked into their narrow streets.

Getting there

Airports nearby:

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

By Car:

Motorway exit at Castellina-in-Chianti, 15 minutes’ drive including a long and rough white road that is not suitable for low-slung cars. Ample parking.

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 guest houses 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

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.
  • Bed linen(2)
  • Bath towels(2)
  • Swimming towels(2)

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
Very efficient with no stone unturned
Mr William Leach
United Kingdom
product comment
"Wonderful house with absolutely everything one could wish for in a magnificent setting. Excellent kitchen with every gadget and utensil you could possibly need and the Pizza oven in the courtyard provided a new cooking adventure for us! Great living areas both inside and out and a large pool, meant we could all be together whenever we wished, but could equally find a separate space to chill out in. The Bedrooms also worked well for that number of people and were very comfortable. Giorgio the manager/caretaker is a very pleasant guy, extremely helpful and very knowledgeable and we enjoyed two great wine tours with him. Easy journey into Castellina which has great selection of shops, bars and restaurants.Good animal spotting to be had on the drive home at night on the slightly challenging unmade road, we saw porcupine, wild boar and deer! We would certainly be happy to make a return visit to this lovely house."
service comment
Service I received was good throughout, and description of the villa booked was totally accurate so a very happy experience.
Mr Brian Davies
United Kingdom
product comment
The villa was exactly as described. In addition there is a wood burning oven that we used to make pizza's and grill a Tuscan Florentine steak. Winery with tasting room is within walking distance. The pool was great even in the early evening. We used all the rooms. The only thing that might have been improved was the wifi. The thick walls block signal so if you move to other rooms the signal is lost.
service comment
Andrea and Giorgio were helpful with the lost luggage. They were available to answer questions. Maid service came by as scheduled.
Mr Edward Chien
United States


Collected by us from our feedback forms we send to all our clients

Thank you for the wonderful week! Magical vacation in a beautiful home! Pietro's cooking was to die fro! The host's home was cozy and perfect for a week of relaxation! We had a wonderful holiday, thank you! Lawrence Family - England and Toronto, Canada
Mr Paul Lawrence
United Kingdom
We've had 3 enjoyable weeks in Chianti! Weather has been very hot and the pool has been much enjoyed. Do visit: 1) Brancaia winery, Paolo / Laura give a great tour and the wines are very good. 2) Rocca delle Macíe and their restaurant (Fizzanno), 3) Castello di Ama, superb installations (great tour). And...then have lunch or dinner in their excellent restaurant. 4) Gelato in Castellina. Superb! 5) Best restaurant in the area is Albergaccio in Castellina, superb : Francesco, Sonia (chef) and Pietro( 2nd chef) are lovely people. Pietro, the chef, come to the villa and cooks up a storm!
Mrs Kate Newman
United Kingdom
Thank you for sharing your beautiful home with us! My family had an AMAZING time exploring the Tuscan hillsides and Italian hill-towns (why anyone else would want to live anywhere else beyond me). It seemed as trough every day we discovered something new and exciting! The kids loved the pool. (and who wouldn't?) And we all enjoyed looking out over the countryside and taking in the beautiful views. I even tried wine for the first time! Your lovely home was the perfect conclusion to every bright and busy day! What more could anyone ask for? Thank you so, so much! Ciao, Maddie, Andrew, Sarah, Anne, Ron, Mary and Tim - Connecticut, USA
Ms Anne Ritter
United States
We had a wonderful week exploring the hill towns of Tuscany, tasting the wines, shopping in Florence, balloning over the countryside. This home was the perfect respite for relaxing after the adventures of the day! We loved it! Grazie! The Schweizer Family - New York City - USA
Mrs Alison Schweizer
United States
We've had an absolutely great week enjoying everything this beautiful old house in its idyllic setting can offer - into wonderful weather too! The pool, watching the wildlife (wild boar, deer,buzzard, swallows, lizards, porcupine), the countryside, stunning local towns have kept us well occupied. the time has flown by! The Peggie family - UK
Mrs Margaret Ann Peggie
United Kingdom
We very much enjoyed our week at Il Trebbio in spite of the weather being not so good. The villa was very well equipped and we were all very comfortable in our bedrooms/bathrooms. It really does have a wonderful location and the 10 minute drive on the rough road was not a problem! We will certainly recommend it to our friends. Kind regards Ian Maitland
Mr Ian Maitland
United Kingdom
We absolutely loved everything about the villa! The location was idyllic, the views perfect and the memories from staying there are happiness and contentment. The interior was comfortable and spacious, perfectly equipped for so many people, and the gardens, courtyard and pool were like being in a dream. We are so appreciative we got to spend time together in this home.
Ms Katy Jenkins
United Kingdom
Villa Il Trebbio was exactly as described. The bedrooms and bath facilities were excellent and easily accommodated 6 adults and could handle more. There were many common rooms with comfortable seating to enable anyone to 'escape' to read, nap or just relax. The kitchen and its appointments were fantastic. It was our gathering room throughout the day when we were in the Villa. What was most special was the way the owners cared for the property, and now we know more about the owner's beautiful creations in pottery...we were blessed to use all his fine pottery for every meal, as well as looking at all the artwork in the home. This was special! We had cooking service with Sonya and her husband Marcello. We had three dinners planned, and we worked closely with them on the menu. None of the guests spoke Italian, but Marcello and Sonya were most proficient with a translation App and we had a great time communicating with each other.
Mr John P Clancey
United States
If you are looking for a place to relax and experience Tuscany as you imagine this is the place. Private, relaxing and peaceful. With space for everyone to come together or find that quiet corner. Located centrally there are so many places to visit and explore or just lie by the pool and watch the day drift. Wonderful experience.
Mrs Elaine Morley
New Zealand


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Services available on demand

N.B.: Please note that prices and availability for the following services are subject to change and should be paid locally and directly to the supplier of the single service required.
  • {{ 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 20 7684 8884

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