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Search results; Over 1,000 homes in Castelfiorentino

Guest favourite
Flat in Castelfiorentino
Strategic location, relaxation in the Tuscan countryside
1 bedroom, 2 beds, 1 private bathroom
10–15 Oct
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4.9 out of 5 average rating, 29 reviews
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with pool
4 bedrooms, 6 beds, 4.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Montaione
Punteriolo Spereto Family Apartment With Pool, - P
2 bedrooms, 2 beds, 1.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Gambassi Terme
Il Fienile, Luxury Apartment in the Tuscan Hills
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 232 reviews
Guest favourite
Farm stay in Montaione
Tenuta Collerucci | Villa with private pool
10 bedrooms, 9 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 7 reviews
Guest favourite
Villa in La Valle
Vallecchio in Tuscany
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in San Miniato
16th Century Tuscan Estate Near Florence.8
3 bedrooms, 5 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds, 3.5 bathrooms
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Palaia
Casa Billi
2 bedrooms, 2 double beds, 1.5 bathrooms
2–7 Oct
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
6 bedrooms, 6 beds, 4.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Volterra
Vacation home with private pool, view
2 bedrooms, 3 beds, 1 bathroom
31 Oct – 5 Nov
5.0 out of 5 average rating, 15 reviews
Villa in Gambassi Terme
La Striscia Villa Farm with Private Pool
4 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 3 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
3 bedrooms, 4 beds, 3 bathrooms
23–28 Sept
5.0 out of 5 average rating, 3 reviews