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Search results; Over 1,000 homes in Castelfiorentino

Top guest favourite
Rooms in Castelfiorentino
Beautiful view of the Tuscan hills
10 bedrooms, 3 beds, 8 private bathrooms
26–31 Oct
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5.0 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Castelfiorentino
Casa al Profeti
2 bedrooms, 2 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Montespertoli
Villa Tirinzano for 14 guests with private pool
7 bedrooms, 11 beds, 7 bathrooms
3–10 Apr
4.94 out of 5 average rating, 35 reviews
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
New place to stay
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds, 3 bathrooms
13–18 Jul
5.0 out of 5 average rating, 9 reviews
Flat in Badia a Passignano
Maison Badia a Passignano, Ciliegiolo
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
Top guest favourite
Farm stay in Lastra a Signa
Farmhouse in Tuscany hills
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 109 reviews
Flat in San Miniato
Tuscan Palazzo with Original Frescoes & Views
2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Gambassi Terme
Il Fienile, Luxury Apartment in the Tuscan Hills
1 bedroom, 2 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 221 reviews
Villa in Gambassi Terme
La Striscia Villa Farm with Private Pool
4 bedrooms, 6 beds, 3 bathrooms
29 Aug – 5 Sept
Tower in San Donato
Luxury apartment in an 1100s tower
1 bedroom, 3 beds, 1 bathroom
31 Jul – 5 Aug
Top guest favourite
Flat in Peccioli
Dante's Way - Nature, Simplicity and Beauty
2 bedrooms, 2 beds, 2 bathrooms
3–8 Sept
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Room in Lastra a Signa
Sposa Mea
1 bed, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 60 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, 104 reviews
Top guest favourite
Home in Gambassi Terme
La Cipressina Relax in Tuscany
1 bedroom, 1 double bed, 1 bathroom
22–27 Oct
5.0 out of 5 average rating, 109 reviews
Top guest favourite
Home in Barberino Tavarnelle
Relax in Tuscany Country Home with a Stunning View
1 bedroom, 2 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
2 bedrooms, 3 beds, 4 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 10 reviews
Home in Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
4 bedrooms, 5 beds, 3 bathrooms
1–6 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Montaione
Exclusive Villa in Tuscany
13 bedrooms, 16 beds, 15.5 bathrooms
10–15 Jul
4.93 out of 5 average rating, 15 reviews