Search Vacation Homes in Castiglion Fiorentino

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Our top choices for Castiglion Fiorentino vacation homes

1. 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 AED 2,115
AED 2,791 total
includes taxes & fees
8 Dec - 9 Dec
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning

2. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is AED 941
AED 1,121 total
includes taxes & fees
16 Nov - 17 Nov
Arc two-bedroom apartment

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

Pheasant swimming pool flat with 3 bedrooms and two bathrooms
Toscana
The price is AED 1,412
AED 1,715 total
includes taxes & fees
16 Nov - 17 Nov
Pheasant swimming pool flat with 3 bedrooms and two bathrooms

4. La Lepre swimming pool flat with 3 bedrooms and two bathrooms

La Lepre swimming pool flat with 3 bedrooms and two bathrooms
Toscana
The price is AED 1,412
AED 1,715 total
includes taxes & fees
16 Nov - 17 Nov
La Lepre swimming pool flat with 3 bedrooms and two bathrooms

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 AED 1,412
AED 1,674 total
includes taxes & fees
16 Nov - 17 Nov
Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms

6. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is AED 276
AED 399 total
includes taxes & fees
9 Nov - 10 Nov
Dolce Casa 2 by Tiny Away

7. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is AED 299
AED 422 total
includes taxes & fees
9 Nov - 10 Nov
Dolce Casa 1 by Tiny Away

8. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is AED 486
AED 593 total
includes taxes & fees
11 Nov - 12 Nov
Holiday Home 'La Casina All'angolo'

9. 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 AED 293
AED 604 total
includes taxes & fees
9 Nov - 10 Nov
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

10. 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 AED 258
AED 303 total
includes taxes & fees
9 Nov - 10 Nov
Vacation home with a panoramic terrace, ideal for families and couples

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 AED 314
AED 331 total
includes taxes & fees
9 Nov - 10 Nov
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

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 AED 323
AED 368 total
includes taxes & fees
11 Nov - 12 Nov
Montecchio di Cortona

13. 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 AED 472
AED 488 total
includes taxes & fees
9 Nov - 10 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

14. 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 AED 1,477
AED 1,648 total
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

15. 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 AED 457
AED 829 total
includes taxes & fees
11 Nov - 12 Nov
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

16. 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 AED 2,022
AED 2,192 total
includes taxes & fees
9 Nov - 10 Nov
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

17. 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 AED 4,492
AED 4,492 total
includes taxes & fees
11 Nov - 12 Nov
Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

18. Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi
Monte San Savino
The price is AED 951
AED 1,327 total
includes taxes & fees
11 Nov - 12 Nov
Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

19. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is AED 305
AED 397 total
includes taxes & fees
9 Nov - 10 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

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 AED 2,619
AED 2,644 total
includes taxes & fees
29 Nov - 30 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.

Learn more about Castiglion Fiorentino

Climb the medieval walls of this hilltop town for sweeping views across Tuscany's Val di Chiana countryside. Explore the Etruscan Archaeological Museum inside Palazzo Casali, then enjoy aperitivo with locals in Piazza del Municipio.

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

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