Entire home
Charming Cottage with Pool, Nestled in the Heart of Val Di Chiana.
Cottage in Castiglion Fiorentino with private pool and kitchen
Photo gallery for Charming Cottage with Pool, Nestled in the Heart of Val Di Chiana.





Reviews
9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4807.3 sq ft
Popular amenities
Explore the area

Castiglion Fiorentino, Arezzo
- Place, Tennis Club Castiglionese3 min drive
- Place, Cassero Tower3 min drive
- Place, Archaeological Museum3 min drive
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 2
2 Single Beds
2 bathrooms
Bathroom 1
Bathroom 2
Spaces
Deck or patio
Kitchen
Garden
Dining area
About this property
Charming Cottage with Pool, Nestled in the Heart of Val Di Chiana.
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 for exclusive use of your group.
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.
Two 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
“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 for exclusive use of your group.
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.
Two 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
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Pet-friendly
Free WiFi
Outdoor space
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Villa with pool and garden
Villa with pool and garden
- Pool
- Kitchen
- Washer
- Pet-friendly
10.0 out of 10, Exceptional, (83 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: less than 25 kg per pet (limit one pet total)
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is no smoke detector on the property
Property Registration Number IT051012C2FUWPHICR
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
Castiglion Fiorentino
Castiglion Fiorentino is home to this cottage. Tennis Club Castiglionese and Agricola Buccelletti Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Lake Trasimeno and Area Naturale Protetta di Interesse Locale Bosco di Sargiano. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with mountain biking, horse riding and cycling.

Castiglion Fiorentino, Arezzo
What's nearby
- Tennis Club Castiglionese - 3 min drive - 2.2 km
- Cassero Tower - 3 min drive - 2.5 km
- Archaeological Museum - 3 min drive - 2.5 km
- Municipal Art Gallery - 3 min drive - 2.5 km
- Lake Trasimeno - 26 min drive - 24.5 km
Getting around
Restaurants
- Osteria Le Rughe Di Cortona - 13 min drive
- Trattoria Etrusca - 13 min drive
- Relais Il Falconiere Hotel Cortona - 10 min drive
- Bar Delle Mura - 5 min drive
- Il Passaggio - 3 min drive
Frequently asked questions
Reviews
9.8
Exceptional
10/10
Cleanliness
10/10
Check-in
10/10
Communication
9.6/10
Location
10/10
Listing accuracy
Reviews
23 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Sep 2025
10/10 Excellent
Andreas G.
3 Nov 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic outlook
Andreas G.
Stayed 6 nights in Oct 2020
8/10 Good
Bruno u. Karen H.
11 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Very relaxing stay...
Bruno u. Karen H.
Stayed 14 nights in Sep 2023
10/10 Excellent
Vincent M.
19 Jul 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy



Vincent M.
Stayed 7 nights in Jul 2025
10/10 Excellent
Andrea F.
15 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tolles Haus in schöner Lage
Andrea F.
Stayed 12 nights in Sep 2024
10/10 Excellent
Lorène B.
26 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent séjour
Lorène B.
Stayed 7 nights in Aug 2024
8/10 Good
Kerstin P.
12 Jul 2023
Liked: Cleanliness, check-in, communication, listing accuracy
Landhaus bei Cortona
Kerstin P.
Stayed 7 nights in Jul 2023
10/10 Excellent
Michael R., Langenbrettach
12 Sept 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Eine schöne Woche in Poggiolo
Michael R.
Stayed 7 nights in Sep 2022
10/10 Excellent
Thomas N.
2 Sept 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wunderschöner Aufenthalt
Thomas N.
Stayed 5 nights in Aug 2022
10/10 Excellent
Thorsten Z.
13 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Traumhafter Familienurlaub
Thorsten Z.
Stayed 14 nights in Jul 2022
10/10 Excellent
Corinna B.
31 Jul 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wunderschön und sehr familienfreundlich
Corinna B.
Stayed 14 nights in Jul 2022
10/10 Excellent
Caroline W.
8 Apr 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Super
Caroline W.
Stayed 5 nights in Mar 2022
10/10 Excellent
Eduard Z.
8 Aug 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Grazie per tutti - vielen Dank für alles!
Eduard Z.
Stayed 7 nights in Jul 2021
10/10 Excellent
Christian K.
9 Sept 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
wundervolles Ambiente
Christian K.
Stayed 7 nights in Aug 2020
10/10 Excellent
Livia d.
1 Aug 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful stay
Livia d.
Stayed 5 nights in Jul 2020
10/10 Excellent
Claire v.
22 Jun 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
South Toscany
Claire v.
Stayed 13 nights in Jun 2019
10/10 Excellent
Lisa W.
8 Jun 2019
gracious host
Lisa W.
Stayed 4 nights in May 2019
10/10 Excellent
Michael C.
19 Apr 2019
Wonderful place
Michael C.
Stayed 5 nights in Apr 2019
10/10 Excellent
Nicola S.
22 Oct 2018
Clean & comfortable cottage run by a lovely family.
Nicola S.
Stayed 14 nights in Sep 2018
10/10 Excellent
Jenny V.
12 Sept 2018
Comfortable and stylish
Jenny V.
Stayed 7 nights in Sep 2018
8/10 Good
Sian S.
18 Aug 2018
Beautiful Property
Sian S.
Stayed 7 nights in Aug 2018
10/10 Excellent
Yvonne S., Encinitas
9 Jul 2018
Magical Family Getaway
Yvonne S.
Stayed 7 nights in Jun 2018
This review comes from a trusted partner site and has not been verified.
10/10 Excellent
Michael D.
16 Jun 2018
Lovely
Michael D.
Stayed 7 nights in Jun 2018
This review was submitted before 2018 and has not been verified.
8/10 Good
Andrea V.
21 Apr 2017
bellissimo
Andrea V.
Stayed 4 nights in Apr 2017
This review was submitted before 2018 and has not been verified.
10/10 Excellent
Karole J.
15 May 2016
We loved this place and people
Karole J.
About the host
Hosted by ANNA ROSSI
Why they chose this property
What makes this property unique
Languages:
English, Italian
Tell us how we can improve our siteShare feedback






![Holiday Home Exterior [summer]](https://media.vrbo.com/lodging/102000000/101570000/101565100/101565050/b32cc2d7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

![Holiday Home Exterior [summer]](https://media.vrbo.com/lodging/72000000/71670000/71662100/71662063/2a7312f0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

![Holiday Home Exterior [summer]](https://media.vrbo.com/lodging/77000000/76150000/76145200/76145160/50cdd409.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium)

















