Il Condottiero

Castiglion Fiorentino, Toscana

Beatiful villa with extremely panoramic pool, situated only 4 km from Castiglion Fiorentino. In rustic Tuscan style. Suitable for families or groups of friends who wish to combine the relaxing life of the countryside with tours of Tuscany.






Swimming pool

  • TV
  • Dishwasher
  • Washing machine
  • Air conditioning
  • Private pool
  • Barbecue
  • Pets Allowed
  • Parking
  • Microwave
  • Oven
  • Fenced
  • Fireplace


Il Condottiero is a beautiful farmhouse set in the hills covered with olive groves, between Castiglion Fiorentino and Cortona, in an extremely panoramic position. You will be within walking distance of the superb medieval castle of Montecchio Vesponi, with its imposing tower rising over the valley.
The village of Castiglion Fiorentino, with shops and services of all kinds, is only 4 km away and offers many folkloristic and cultural events, especially during the summer, as does the ancient Etruscan town of Cortona, which is only 8 km away. It is impossible not to recommend a visit to Cortona and a stop at "Rugapiana" for an ice cream or an aperitif. The town, with its stone streets and historic buildings perched on the hill, will remain in your heart.

The farmhouse is tastefully decorated in a comfortable, rustic Tuscan style. The furniture chosen, the colours with which the walls have been painted, the wrought iron beds, the curtains and the furnishings, all blend in perfectly with the ancient characteristics of the structure.
On the lower floor, the large masonry kitchen also serves as a dining room.
The huge fireplace, the woven wicker baskets and the copper pots and pans will immerse you in a warm atmosphere of times gone by.
Il Condottiero is perfect if you are travelling as a family or with a group of friends, wishing to combine a relaxing holiday by the pool surrounded by the Tuscan countryside with tours and day trips throughout central Italy. 

The garden is enclosed and surrounded by olive, almond and cypress trees and is well equipped with outdoor furniture, barbecue and wood-burning oven. It will be a space of pleasant relaxation and refuge on hot summer days and the ideal place for your dinners or barbecues with friends. For a chat and a glass of wine on the side of the house there is a small pergola with table and sofas. At your disposal and for your exclusive use is the beautiful swimming pool (size 5x10 m - depth 1.40 - open from 01st May to 30th September) situated on a natural terrace, with stone solarium, sunbeds and umbrellas. The fantastic view of the Valdichiana from here will enchant you with its changing colours, at any time of the day, from dawn to dusk.

Luca, the owner, will be happy to organise for you trekking or mountain bike excursions with local guides to discover the paths in the area, ceramics, painting and cookery courses and many other activities to live an unforgettable Tuscan experience.

Interior description

GROUND FLOOR: wide kitchen-dining room with fireplace, small bathroom with shower, double bedroom.
FIRST FLOOR: with access either through internal wooden staircase or external staircase with typical loggia, living room with fireplace and single sofa bed, study with single sofa bed, double bedroom with small private bathroom with shower, double bedroom, double bedroom with added single bed, bathroom with shower. The 3 bedrooms on the first floor are endowed with air conditioning.


  • Dishwasher, microwave, refrigerator with freezer, filter coffee maker, oven
  • Wi-Fi Internet access, DVD player, satellite TV
  • Washing machine, high chair, air conditioning.


Castiglion Fiorentino

Airport di Firenze

Highway A1 Monte San Savino

Hospital of Fratta


Attention please select the dates that interest you.
N. of people
N. of nights
Total price

Notes on price

 Arrival: in the afternoon between 4 p.m. and 7 p.m. - Departure: in the morning between 8 a.m. and 10 a.m. Possibility of late Check-in until Midnight with an extra charge of Euro 50.

WELCOME BASKET for dinner and breakfast Euro 60.


Private pool open from 01/05 to 30/09.
Pets allowed.
Swimming towels available on request.
Air Conditioning.
High speed Wi-Fi Internet access (20 MEGA).
Wood for fireplace.
Bed linen and bathroom towels (Initial Set).
One baby bed (for children up to 3 years) on request at time of booking.

Breakage deposit Euro 200 (payable in cash on your arrival and held by the owner for the duration of your stay). During their stay, should travellers cause any damage to the property, they will be liable for the associated costs. 
Electric car charging on demand on payment.
Obligatory final cleaning Euro 150.
Heating Euro 30 per day (if used).
Tourist Tax Euro 1 per person per day, applied for the first 7 days only, children up to 14 years do not pay.

To make a reservation you can book directly on the site by selecting the dates in the calendar of the desired accommodation, or you can send an e-mail to specifying the name of the villa and the period you want to book and we will send you our booking confirmation with all the details to proceed with the payment.

Methods of payment (by bank transfer or Credit card)
At the time of booking confirmation we will require the payment of a deposit of 20% the total amount of the booking.
The payment of the balance is required within 35 days before the beginning of the stay.
If the booking is made within 35 days prior to the start of the rental period, the amount must be paid in full upon confirmation of the booking.

Cancellation terms
-20% of the rental price for cancellations received up to 36 days before the rental.
-100% of the rental price for cancellations received between the 35th day and the day of commencement of the rental, and in case of No Show.


  1. Liesbeth (Netherlands)Published on: 09/08/2022

    I would immediately recommend it to anyone.

    The house was very clean, has a very nice location. The beautiful garden with the swimming pool is definitely an added value. We did find that we had too little storage space in the kitchen, but we used the huge big beautiful table to store everything. We brought our own extra table which we immediately used outside to sit a bit comfortably, the next day the owner brought a new extra table. Owner very helpful and friendly, he lives next door, but this did not cause any problems at all. We really enjoyed it, we will definitely go back again. It is a very nice house with a beautiful garden. They were also ready every time there was a problem e.g. electricity cut during a thunderstorm. Thank you for the hospitality! I would immediately recommend it to anyone.

  2. Julien (France)Published on: 28/08/2019

    Très belle maison

    Très belle maison privée située près de la ville pittoresque et charmante de Castiglion Fiorentino. Supermarchés, gare, restaurants à proximité (10 min en voiture). Accueil parfait, très bonne communication. Décoration traditionnelle, beaucoup d'espace int et ext, et ensemble très confortable. Piscine nettoyée chaque matin. Beaucoup de mobilier ext mis à disposition. Je recommande, sans hésitation.

  3. Taija (United Kingdom)Published on: 22/07/2019

    Traditional italian house

    This was our (two families) second time in this wonderful, traditional italian house. We just love it and its magnificent swimming pool and huge garden. Owner is also very kind and helpful, whenever we needed help. Perfect place for those who need a peaceful and relaxing holiday. However the house is close to lovely cities like Cortona, Arezzo and Florence.

  4. Xavier (Belgium)Published on: 21/08/2017

    agréable vacances

    Nous avons passé de très agréable vacances dans cette villa. Vue dégagé, grand jardin (top pour les enfants), chambre agréable, four à Pizza Mais une seule table 8 personnes dehors, 6 transats, table extérieur assez éloignée de la cuisine, cuisine limite pour 8 personnes (petit frigo, petite tac, ..) et une seule sdb réellement utilisable. Ceci étant, cela nous a pas empêché de passer un excellent séjour !

  5. Nora (Hungary)Published on: 24/09/2016

    Beautiful hidden place

    If you are looking for a hidden place, where none disturbs you, you should choose Casolare Il Condottiero! The owner is very kind and helps you to organize your free time and gives advice where to go and what to do. You can visit Florence, San Gimignano, Siena, Montepluciano and Cortona easily, by car or by train as well. The house has an authentic spirit with the inside furnitures. The view is beautiful, as it was built on the hillside. The garden is huge with pool and BBQ area. We took our dogs with us and they enjoyed the big field as well. I can recommend for those who are looking for a farmhouse with big surface in a tranquil environment and would like to explore the southern part of Tuscany.

  6. Essukka (Finland)Published on: 26/09/2015

    Beautiful villa with amazing view

    We spent one week in Casolare Il Condottiero at June-July 2015 with my family, my parents and my hubs parents. Very nice and beautiful villa with amazing view. Pool and garden were great, specially for children. The owner was very friendly and told us some great tips about Tuscany. Thanks for amazing vacation!

Il Condottiero CIR: 051012AAT0056