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Search results; Over 1,000 homes in Chianni

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Top guest favourite
Cottage in Chianni
Cozy Italian stone cottage central Tuscany
3 bedrooms, 4 beds, 2 private bathrooms
21–26 Sept
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4.94 out of 5 average rating, 72 reviews
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Top guest favourite
Villa in Castagneto Carducci
sea view villa with private infinity pool
Business host
10–17 Oct
4.99 out of 5 average rating, 123 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Guest favourite
Flat in San Gimignano
Teruzzi Country House - Apartment La Buvette
Individual host
18–23 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Villa in Castel Focognano
Villa Marinelli: pool, hot tub & garden, Tuscany
Individual host
14–19 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
Individual host
8–13 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Villa in San Casciano In Val di Pesa
Archipettoli - Exclusive villa 360 view AC WIFI
Individual host
19–26 Sept
5.0 out of 5 average rating, 13 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
16–21 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Pelago
Tuscan vineyard home. Near Florence
Individual host
10–17 Oct
5.0 out of 5 average rating, 73 reviews
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Superhost
Home in Greve in Chianti
Villa with swimming pool in the heart of Chianti | Florence
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Home in Colle di Val d'Elsa
Casa Emilio
Business host
23–28 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
Individual host
18–23 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Pisa
Greenhouse Seal
Business host
10–15 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Flat in Montaione
Punteriolo Spereto Family Apartment With Pool, - P
Business host
29 Sept – 4 Oct
4.89 out of 5 average rating, 9 reviews
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Top guest favourite
Barn in Pontassieve
Your little slice of paradise near Florence
Individual host
15–20 Nov
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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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
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
17–24 Oct
5.0 out of 5 average rating, 19 reviews