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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
2–7 Sept
New place to stay
Top guest favourite
Apartment in Castelfiorentino
Casa al Profeti
2 bedrooms, 2 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in San Miniato
16th Century Tuscan Estate Near Florence.8
3 bedrooms, 5 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 7 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
Villa in Noce
Historic villa with private pool in Tuscany
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Castelfiorentino
Casa Farsetti
4 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 6 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
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
2 bedrooms, 3 beds, 4 bathrooms
2–7 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Villa in La Valle
Vallecchio in Tuscany
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in La Serra
Casa Orlando | Private Pool Villa in Tuscany
3 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
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
6–11 Sept
4.99 out of 5 average rating, 113 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
Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
3 bedrooms, 4 beds, 3 bathrooms
23–28 Sept
New place to stay
Superhost
Home in Montespertoli
Casa Greta - Flo Apartments
2 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
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
Top guest favourite
Home in Volterra
Vacation home with private pool, view
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Villa in Peccioli
Villa Bonriposo
5 bedrooms, 7 beds, 6 bathrooms
14–19 Sept
5.0 out of 5 average rating, 9 reviews