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Search results; Over 1,000 homes in Montalcinello

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Farm stay in Montalcinello
12th-century Medieval House • Private Pool & Park
4 bedrooms, 4 beds, 2 private bathrooms
5–10 Sept
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4.89 out of 5 average rating, 38 reviews
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Superhost
Villa in Montalcinello
Elegant villa with private pool near San Galgano
8 bedrooms, 11 beds, 4 bathrooms
5–12 Sept
4.8 out of 5 average rating, 15 reviews
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Top guest favourite
Villa in Roccastrada
Winefarm in Tuscany with pool, ideal for groups.
15 bedrooms, 23 beds, 12 bathrooms
2–7 Nov
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Villa in Radicondoli
Leo's Romantic House
4 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Chiusdino
La Capanna: country house with magnificent view
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.92 out of 5 average rating, 83 reviews
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Top guest favourite
Flat in Radicondoli
Tuscan Hilltop Retreat | Views, Charm, Fireplace
3 bedrooms, 3 beds, 3 bathrooms
21–26 Sept
4.98 out of 5 average rating, 48 reviews
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Villa in Radicondoli
Villa Le Bolli, a holiday to be loved
12 bedrooms, 21 beds, 13 bathrooms
2–7 Nov
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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Top guest favourite
Flat in Roccatederighi
Domus Olea BnB
1 bedroom, 1 queen bed, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 38 reviews
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Superhost
Flat in Ampugnano
Villa Fausta Apartment
1 bedroom, 2 beds, 1.5 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Flat in Chiusdino
Casa Betta – 700-Year-Old Tuscan Gem
1 bedroom, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 40 reviews
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Home in Castel San Gimignano
Elegant private cottage Volterra–San Gimignano
1 bedroom, 2 beds, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Casino
The Cottage in the Garden
1 bedroom, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
1 double bed, 1 bathroom
2–7 Sept
4.95 out of 5 average rating, 160 reviews
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Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
1 bedroom, 4 beds, 1 bathroom
8–13 Oct
4.98 out of 5 average rating, 64 reviews
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Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.99 out of 5 average rating, 82 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 385 reviews