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Search results; Over 1,000 homes in Chianni

Guest favourite
Home in Chianni
Tuscan Dream Villa
5 bedrooms, 5 beds, 5 private bathrooms
29 Sept – 4 Oct
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5.0 out of 5 average rating, 11 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
Top guest favourite
Villa in Castagneto Carducci
sea view villa with private infinity pool
3 bedrooms, 5 beds, 2 bathrooms
10–17 Oct
4.99 out of 5 average rating, 123 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
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 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
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
2 bedrooms, 3 beds, 4 bathrooms
8–13 Oct
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in San Gimignano
Teruzzi Country House - Apartment La Buvette
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 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
Top guest favourite
Apartment in Scandicci
Vintage Residence with Pool in Chianti
1 bedroom, 2 beds, 1 bathroom
7–12 Oct
4.96 out of 5 average rating, 146 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
2 bedrooms, 2 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 10 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 Pisa
Tenuta del Serra
4 bedrooms, 4 beds, 4 bathrooms
10–15 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
4 bedrooms, 5 beds, 3 bathrooms
26–31 Mar
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Barn in Pontassieve
Your slice of paradise near Florence
1 bedroom, 2 beds, 1 bathroom
23–28 Nov
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Gambassi Terme
La Cipressina Relax in Tuscany
1 bedroom, 1 double bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 120 reviews
Top guest favourite
Villa in Castel Focognano
Villa Marinelli: pool, hot tub & garden, Tuscany
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Pelago
Tuscan vineyard home. Near Florence
3 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 72 reviews
Tower in San Donato
Luxury apartment in an 1100s tower
1 bedroom, 3 beds, 1 bathroom
20–25 Nov