Charming Cottage with Pool, Nestled in the Heart of Val Di Chiana

  • House
  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 2


This charming cottage is nestled in the heart of the beautiful Val di Chiana, a few minutes’ drive from the picturesque hilltop town of Castiglion Fiorentino and 15 minutes from Cortona. Here you can enjoy the peace and quiet of the Tuscan countryside and all the benefits of a lively historical town not far away.
“La Tabaccaia” was originally built in the early 20th century and used to dry tobacco leaves grown on nearby farms. The building has recently been restored with much care, preserving its authenticity and charm while fusing it with the comforts of modern times. On the same property is the main “farmhouse” where the discreet and helpful owners reside. Anna and her parents Fausto and Flavia can help you get settled in, plan activities, and answer questions about the area. (We speak and understand English!)
The 5000 m2 fenced property includes olive trees, oak trees, spacious lawns and a large swimming pool, open from May to September, with a delightful view of nearby Castiglion Fiorentino.

The pool is surrounded by gardens filled with lavender and rosemary. There, you will find comfortable lounge chairs for your relaxing pleasure and an outdoor shower. Pool towels are included in the rental rate. The pool is shared with other guests (max 3) who occupy an apartment in the villa.
The house consists of two floors which can comfortably accommodate 4+1 adults.
Ground Floor
1 open living area – including kitchen/dining, and satellite TV
1 full, smaller bathroom with a sink, shower, and toilet
1 bedroom with twin/single beds
Second Floor
1 master bedroom with dressing area
1 full bathroom with a sink, shower, toilet
Bedding, towels, electricity, wifi are included in the rental rate. Heating is not included.
Additional amenities for our guests include complimentary Internet (Wi-Fi). Our guests can enjoy the large yard for relaxing, playing with their children, and dining at the outdoor table under a gazebo. The views of Castiglion Fiorentino and the surrounding countryside are always with you at this hilltop retreat. There is also a charcoal barbeque on site for guest use.
Three touring bicycles are available to guests who might enjoy a slower paced, albeit challenging, exploration of the nearby countryside.
Guests may use the laundry area on the ground floor of the owners’ house, which includes a washing machine. Clothes may be hung on a rack to dry.
The owners live in the main house on the property and are available should you require assistance. We are happy to give you recommendations and help make reservations for local dining. We can also give you advice on what to do or see in the area.
La Tabaccaia is located in southern Tuscany, with easy access to interesting destinations. By car, we are 2.5 hours north of Rome, just over an hour south of Florence, 45 minutes east of Siena, and 40 minutes from Montepulciano, Perugia and numerous other beautiful Tuscan towns. The property is just a few minutes from the Castiglion Fiorentino train station on the Rome – Florence train line.

Keywords: cottage, holiday house, pool


  • Iron and board
  • Basic soaps
  • Linens provided
  • Toilet paper
  • Towels provided
  • Washing machine
  • Hair dryer
  • Wireless internet
  • Heating
  • Barbecue
  • Bathroom
  • Swimming Pool
  • Outside Living
  • Parking
  • Satellite / Cable
  • DVD player
  • Pool table
Pool and spa facilities
  • Swimming pool
  • Private pool
  • Museums
  • Winery tours
Leisure Activities
  • Outlet shopping
  • Horseback riding
  • Antiquing
Sports and Adventure Activities
  • Cycling
  • Mountain biking
  • Swimming
  • Mountain climbing
Kitchen and dining
  • Kitchen
  • Dishes and utensils
  • Microwave
  • Coffee maker
  • Dishwasher
  • Refrigerator
  • Grill
  • Child's highchair
Outdoor features
  • Beach chairs
  • Beach towels
  • Bicycles


Season Nightly Weekly Weekend Monthly Min Stay
Standard Rate
Nov 21st 2023 - Nov 21st 2024
€150 - - - 7
alta stagione
Jul 13th 2024 - Aug 23rd 2024
€165 - - - 7
Additional information about rental rates
  • Cleaning fee €60.00
  • Pet Fee €5
  • Check In 04:00 PM
  • Check Out 10:00 AM
Rental Notes
Rental Policies

Check in after 4:00 PM

Minimum age to rent: 21

Check out before 10:00 AM


Children allowed: ages 0-17


No events allowed


Pets allowed: less than 55 lbs per pet (limit one pet total)


Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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

Onsite parties or group events are strictly prohibited

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 information in the booking confirmation

A car is required for transportation to and from this property

Cancellation Policies

Google Location



gracious host

Lovely views of the valley and hills. We thoroughly enjoyed our stay and our hosts were so helpful with directions to hiking trails and great local restaurants!

Wonderful place

Very nice family and house. We stayed there for several days and visited Tuscany. Great location and close to train and highway. Would definitely stay there again.

Clean & comfortable

Clean & comfortable cottage run by a lovely family.

Comfortable and stylish

We had a cookery lesson which was great fun - learning how to make pasta. The pool was lovely, the kitchen well equipped and the beds comfortable. The only downside was the mosquitoes!

Beautiful Property

We stayed for 7 days in August - a family of 4, including two girls aged 11 and 14. The property was beautifully furnished and included all the extras needed (fans, pool towels, kitchen pans, hair dryer, iron etc). The family gave us a very friendly welcome and were always available for any queries. The view from the terrace is stunning and the pool is beautifully laid out also. We were able to visit lots of interesting towns and Siena/ Florence/ Perugia easily from this location and we loved the region. We would definitely recommend this cottage and the area to other families planning a holiday.

Magical Family Getaway

Our stay in Castiglion Fiorentino far exceeded our expectations. Anna, Fausto, and Flavia were very kind and made sure we were as comfortable as possible. Their hospitality made us want to stay forever! We traveled from Los Angeles with our family of 4 and arrived very tired and hungry. They made sure we had everything we needed to recover from our long travels and pointed us in the right direction for local grocery stores and restaurants in the city center. The scenery was breathtaking and we enjoyed the sunset every night on the lawn with a glass of wine. We will be back!


Had a wonderful stay in the well equipped cottage. We were only staying as a couple with our baby but it could easily accommodate a larger family or two couples.

We loved this place and people

We fell in love with Tuscany and a lot was due to the beautiful experience we had at Flavia and Fausto's villa. This couple and their daughter Anna welcomed us and helped us discover the best parts of Tuscany. The villa was across the property from their home. It was spotless, rustic beauty and homey With amentIties so we could make ourselves at home. If we return with our friends and bring our adult children we'll be fighting over who gets to stay at this villa. Great views, heart of Tuscany, wonderful host homeowners. On the scale of 1 to 5 stars, it's a 10+. Thank you - Karole's and John Jensen, Michigan USA

Very relaxing stay...

The house is individually and tastefully decorated, well equipped with everything necessary and very spacious for 2 people. The windows in the bedroom and kitchen are equipped with solid fly screens - very helpful ;-) The house has a beautiful garden with spacious terrace (great view to Castiglion Fiorentino), which gives a Mediterranean feeling of life. Pool is great situated under olive trees. Shopping facilities in the village are very good. House very well located to explore southern Tuscany and Umbria. Anna, Flavia and Fausto are very accommodating and yet wonderfully reserved - ideal occupation as owners on property and are always available with tips and support. A heartfelt thank you to them from Karen & Bruno

Landhaus bei Cortona

Wir fanden ein sehr ordentlich und sehr gut eingerichtetes Haus vor. Mit unseren 2 erwachsenen Kindern hatten wir ausreichend Platz und den Pool für uns allein! Die Vermieter wohnen im Nachbarhaus. Small talk, aber völlig unaufdringlich. Am letzten Abend wurden wir noch auf einen Vinsanto eingeladen. Sehr liebenswert. Das einzige sämtliche bekannte Ausflugsziele sind weiter entfernt. Da die Temperaturen ziemlich hoch waren mit 38 Grad wägt man ab. Zur völligen Entspannung aber ein Traum. Megaaaa Blick auf Casteligion fiorentino . Einkaufsmöglichkeiten reichlich vorhanden. Insgesamt sehr gut!

Eine schöne Woche in Poggiolo

Wir wurden sehr herzlich und kompetent von Anna empfangen. Sie zeigte uns das Haus und die Einrichtungen, das Grundstück und den schönen Pool. Das Haus war tadellos sauber, sehr stimmig und wertig eingerichtet und sehr gemütlich. Auch die beschattete Freisitzfläche haben wir mit dem wunderbaren Ausblick auf Castiglion Fiorentino sehr genossen. Die voll ausgestattete Küche haben wir wenig genutzt, da uns Anna bereits bei unserer Ankunft diverse Empfehlungen für Restaurants gegeben hatte. Diese haben wir alle genutzt und waren wirklich begeistert. Auch Flavia und Fausto haben uns teilweise beim buchen unterstützt, waren immer für uns da und doch stets angenehm im Hintergrund. Nach ein paar Tagen kamen noch Gäste in das Appartement im Haupthaus. Hier hat die Familie Rossi darauf geachtet, dass kein zweiter Hund mit einzieht. So konnten unsere Freunde den Urlaub mit Ihrem Hund auf dem großzügigen Grundstück entspannt genießen. Für Ausflüge war die Lage perfekt, insbesondere das wunderbare Cortona waren schnell zu erreichen. Auch Arezzo, Montepulciano und der Lago Di Trasimeno sind in gut 30 Minuten erreichbar. Wir sind Freunde der kleinen Allimentari und haben hier direkt in Santa Lucia das La Botteghina gefunden. Hier gibt es alles was das Herz begehrt, auch für das Frühstück und die Verpflegung für die Heimfahrt. Liebe Anna, liebe Flavia und lieber Fausto, herzlichen Dank für die schöne Zeit bei Euch. Wir denken sehr gerne an Euch zurück und werden Euch auf jeden Fall weiterempfehlen. Herzliche Grüße Michael, Gaby, Mike, Laila und Sixten

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