A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Castiglion Fiorentino vacation homes

A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

1. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,968
￥11,863 total
includes taxes & fees
Oct 11 - Oct 12
Happy Nest Tuscany Between Florence and Rome
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

2. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥11,950
￥17,238 total
includes taxes & fees
Oct 13 - Oct 14
Dolce Casa 2 by Tiny Away
Room

3. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥12,939
￥18,252 total
includes taxes & fees
Oct 11 - Oct 12
Dolce Casa 1 by Tiny Away
A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

4. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ￥23,406
￥28,016 total
includes taxes & fees
Oct 31 - Nov 1
Holiday Home 'La Casina All'angolo'
A park with picnic tables, a playground, and a gravel path.

5. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥12,394
￥15,581 total
includes taxes & fees
Oct 14 - Oct 15
Holiday home with panoramic terrace ideal for families and couples
Dining

6. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is ￥13,988
￥17,175 total
includes taxes & fees
Oct 19 - Oct 20
Montecchio di Cortona
A brick building with a large sliding glass door, a brown door, and a small potted plant.

7. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is ￥13,603
￥14,311 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A stone building with a patio area featuring outdoor furniture and potted plants.

8. Podere Casorbica with free parking, large garden, private pool.

Podere Casorbica with free parking, large garden, private pool.
cortona
9.6 out of 10, Exceptional, (18 reviews)
"Giorgio is very welcoming, the house has a very authentic feel. "
Netherlands
Joost B.
The price is ￥27,090
￥31,693 total
includes taxes & fees
Oct 14 - Oct 15
Podere Casorbica with free parking, large garden, private pool.
A building with a stone facade, multiple windows, and a balcony.

9. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is ￥59,079
￥66,443 total
includes taxes & fees
Oct 11 - Oct 12
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A stone building with a balcony, an archway, and potted plants.

10. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is ￥22,672
￥23,380 total
includes taxes & fees
Nov 2 - Nov 3
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A room with a sofa, a wooden cabinet, a table with a vase, and a chandelier.

11. Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony

Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony
Monte San Savino
The price is ￥46,849
￥54,639 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony
A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

12. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
Monte San Savino
6.0 out of 10, (2 reviews)
"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...
Canada
Anonymous traveler
The price is ￥20,746
￥36,882 total
includes taxes & fees
Oct 12 - Oct 13
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

13. Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: The spaciousness of the modern house was perfect. We felt right at home. The big pool was highly appreciated. Cons: -"
United States
Anonymous traveler
The price is ￥95,007
￥102,371 total
includes taxes & fees
Nov 1 - Nov 2
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

14. Double room with private bathroom in the countryside 5 minutes from Montepulciano

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is ￥19,122
￥28,683 total
includes taxes & fees
Oct 13 - Oct 14
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A window with a view of a building with a clock tower, balconies, and a clear sky.

15. Palazzo Cofani Brizzolari – Historic Residence with Tower in the Heart of Arezzo

Palazzo Cofani Brizzolari – Historic Residence with Tower in the Heart of Arezzo
Arezzo Centro Storico
The price is ￥63,125
￥64,189 total
includes taxes & fees
Nov 4 - Nov 5
Palazzo Cofani Brizzolari – Historic Residence with Tower in the Heart of Arezzo
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

16. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ￥17,706
￥21,601 total
includes taxes & fees
Oct 19 - Oct 20
"Il Focolare" Superior Apartment in Monticchiello
A stone building with a pool, surrounded by trees and outdoor seating.

17. -2 / 3-seater garage with private garden, swimming pool, park and spa

-2 / 3-seater garage with private garden, swimming pool, park and spa
sansepolcro (arezzo)
8.4 out of 10, Very good, (5 reviews)
"Het uitzicht was prima, het bed lag ook wel goed, maar ventilatie was niks, waardoor het S’nachts bloedheet was. Het was een verouderde garage, ik zou niemand aanraden dit te boeken. Van park en spa heb ik ook niks gezien."
Netherlands
Sjoukje
The price is ￥15,935
￥29,391 total
includes taxes & fees
Oct 11 - Oct 12
-2 / 3-seater garage with private garden, swimming pool, park and spa
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

18. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveler
The price is ￥25,673
￥35,234 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home in Villa Pandolfina near Montepulciano
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

19. Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
7.0 out of 10, Good, (2 reviews)
"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...
United States
Harald B.
The price is ￥19,122
￥36,474 total
includes taxes & fees
Oct 13 - Oct 14
Romantic farm in the Sienese hills
A kitchen with wooden cabinets, a gas stove, a white dining table with chairs, and a view through a window.

20. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
foiano
The price is ￥194,333
￥194,333 total
includes taxes & fees
Oct 12 - Oct 13
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Castiglion Fiorentino Hotel Reviews

Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

8/10 Good
"Ok."
Yuanjun 1-night trip
Posted 13 hours ago
Hotel Panoramic Montepulciano

Find out more about Castiglion Fiorentino

Castiglion Fiorentino Vacation Homes information

Number of reviews
46
Accommodation
1391 Vacation Homes
Lowest Price
￥11,863
Highest Price
￥194,333