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

Holiday Homes in Castiglion Fiorentino

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Castiglion Fiorentino holiday 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 NZ$133
includes taxes & fees
20 Oct - 21 Oct
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 NZ$1,359
includes taxes & fees
20 Oct - 21 Oct
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 NZ$545
includes taxes & fees
14 Nov - 15 Nov
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 NZ$833
includes taxes & fees
19 Nov - 20 Nov
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 NZ$813
includes taxes & fees
19 Nov - 20 Nov
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 NZ$237
includes taxes & fees
26 Oct - 27 Oct
Dolce Casa 2 by Tiny Away
Room

7. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is NZ$252
includes taxes & fees
25 Oct - 26 Oct
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 NZ$314
includes taxes & fees
31 Oct - 1 Nov
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 NZ$175
includes taxes & fees
26 Oct - 27 Oct
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 NZ$293
includes taxes & fees
8 Nov - 9 Nov
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 NZ$161
includes taxes & fees
20 Oct - 21 Oct
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 NZ$193
includes taxes & fees
21 Oct - 22 Oct
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.
The price is NZ$350
includes taxes & fees
20 Oct - 21 Oct
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 traveller
The price is NZ$414
includes taxes & fees
20 Oct - 21 Oct
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 NZ$746
includes taxes & fees
20 Oct - 21 Oct
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 NZ$263
includes taxes & fees
2 Nov - 3 Nov
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 traveller
The price is NZ$1,150
includes taxes & fees
1 Nov - 2 Nov
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 NZ$318
includes taxes & fees
20 Oct - 21 Oct
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 NZ$614
includes taxes & fees
21 Oct - 22 Oct
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 NZ$720
includes taxes & fees
4 Nov - 5 Nov
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castiglion Fiorentino Hotel Reviews

Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"It's a lovely hotel, but it is the staff that make it truly special. Attentive and cheerful, I felt well looked after from the moment I walked in. Wonderful stay, I'll definitely be back."
Doralba 2-night trip
Posted 1 day ago
Hotel Villa Ricci

Find out more about Castiglion Fiorentino

Castiglion Fiorentino Holiday Homes information

Number of reviews
27
Accommodation
1330 Holiday Homes
Lowest Price
NZ$133
Highest Price
NZ$1,150