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Search results; Over 1,000 homes in Chianni

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Guest favourite
Home in Chianni
The Cottage to relax and enjoy
2 bedrooms, 4 beds, 2 private bathrooms
3–8 Oct
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5.0 out of 5 average rating, 23 reviews
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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, 18 reviews
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Home in Morrona
Villino Isotta (exclusive private villa)
5 bedrooms, 8 beds, 3 bathrooms
15–20 Oct
4.99 out of 5 average rating, 71 reviews
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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, 15 reviews
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Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Barberino Tavarnelle
Peaceful and Relaxing Tuscan Retreat with Views
1 bedroom, 2 beds, 1 bathroom
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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Barn in Pontassieve
Country retreat near Florence with a hot tub
1 bedroom, 2 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 23 reviews
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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, 124 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 18 reviews
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Superhost
Holiday home in Buti
Rivolta Home – Oasi con Vista e Piscina
1 bedroom, 2 beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Greve in Chianti
“Da Me” Apartment
2 bedrooms, 2 double beds, 2 bathrooms
15–20 Oct
5.0 out of 5 average rating, 14 reviews
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Flat in Rignano sull'Arno
VIRGO apartment
2 bedrooms, 2 double beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 28 reviews
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Room in Lastra a Signa
Sposa Mea
1 bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 83 reviews
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Villa in Gaiole in Chianti
Galendino
2 bedrooms, 2 king beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Farm stay in San Gimignano
Casa Renai - holidays with friends in San Gimignano
13 bedrooms, 15 beds, 9 bathrooms
18–23 Oct
5.0 out of 5 average rating, 50 reviews
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Guest favourite
Flat in Volterra
Olive Harmony Tuscan Hideaway
2 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 5 reviews
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Flat in Lajatico
Terrace with a Sunset View of Silence, Apt. Lajatico
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 50 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
27 Oct – 1 Nov
4.95 out of 5 average rating, 58 reviews