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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 ￥7,992
￥11,899 total
includes taxes & fees
Oct 21 - Oct 22
Happy Nest Tuscany Between Florence and Rome
A swimming pool with lounge chairs and a view of mountains in the background.

2. Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning

Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
Castiglion Fiorentino
The price is ￥92,063
￥121,365 total
includes taxes & fees
Oct 21 - Oct 22
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
A patio area with a table and chairs, a wooden pergola, and a view of a kitchen.

3. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is ￥40,846
￥48,660 total
includes taxes & fees
Nov 14 - Nov 15
Arc two-bedroom apartment
A bedroom with a bed, a nightstand, a dresser, a window with curtains, and a wooden ceiling.

4. Pheasant swimming pool flat with 3 bedrooms and two bathrooms

Pheasant swimming pool flat with 3 bedrooms and two bathrooms
Toscana
The price is ￥61,269
￥74,410 total
includes taxes & fees
Nov 14 - Nov 15
Pheasant swimming pool flat with 3 bedrooms and two bathrooms
An outdoor patio with a table and chairs, a stone wall, and a door.

5. Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms

Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms
Toscana
The price is ￥61,269
￥72,634 total
includes taxes & fees
Nov 14 - Nov 15
Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

6. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥15,916
￥21,210 total
includes taxes & fees
Oct 25 - Oct 26
Dolce Casa 2 by Tiny Away
Room

7. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥17,233
￥22,527 total
includes taxes & fees
Oct 25 - Oct 26
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.

8. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ￥23,442
￥28,060 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.

9. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is ￥12,431
￥15,628 total
includes taxes & fees
Oct 26 - Oct 27
Vacation home with a panoramic terrace, ideal for families and couples
A narrow street with buildings on either side, stone walls, and a clear blue sky.

10. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is ￥12,698
￥26,195 total
includes taxes & fees
Nov 8 - Nov 9
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A brick building with a large sliding glass door, a brown door, and a small potted plant.

11. 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 ￥13,644
￥14,354 total
includes taxes & fees
Oct 21 - Oct 22
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Dining

12. 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 ￥14,030
￥17,227 total
includes taxes & fees
Oct 21 - Oct 22
Montecchio di Cortona
A stone building with a patio area featuring outdoor furniture and potted plants.

13. 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.
Podere Casorbica with free parking, large garden, private pool.
A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

14. 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 ￥20,778
￥36,939 total
includes taxes & fees
Oct 21 - Oct 22
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
A building with a stone facade, multiple windows, and a balcony.

15. 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 ￥59,257
￥66,643 total
includes taxes & fees
Oct 21 - Oct 22
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A stone building with a balcony, an archway, and potted plants.

16. 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 ￥22,740
￥23,450 total
includes taxes & fees
Nov 2 - Nov 3
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

17. 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 ￥95,293
￥102,679 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.

18. 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 ￥19,180
￥28,770 total
includes taxes & fees
Oct 21 - Oct 22
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A room with a sofa, a wooden cabinet, a table with a vase, and a chandelier.

19. 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 ￥46,990
￥54,804 total
includes taxes & fees
Oct 21 - Oct 22
Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony
A window with a view of a building with a clock tower, balconies, and a clear sky.

20. 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 ￥63,222
￥64,288 total
includes taxes & fees
Nov 4 - Nov 5
Palazzo Cofani Brizzolari – Historic Residence with Tower in the Heart of Arezzo
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Awesome spot to stay, staff treats you like royalty. Nice little spot to stay for a few days after one of the bigger cities in Italy!"
Shayne 2-night trip
Posted 9 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Castiglion Fiorentino

Castiglion Fiorentino Vacation Homes information

Number of reviews
27
Accommodation
1391 Vacation Homes
Lowest Price
￥11,899
Highest Price
￥102,679