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Search results; Over 1,000 homes in Montaione

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Superhost
Farm stay in Montaione
Villa Il Goro
4 bedrooms, 4 beds, 2 private bathrooms
1–6 Oct
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4.79 out of 5 average rating, 19 reviews
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Guest favourite
Farm stay in Montaione
Tenuta Collerucci | Villa with private pool
10 bedrooms, 9 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 7 reviews
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Villa in Montaione
Exclusive Villa in Tuscany
13 bedrooms, 16 beds, 15.5 bathrooms
15–20 Oct
4.93 out of 5 average rating, 15 reviews
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Flat in Montaione
Apartment in farmhouse with garden and pool
2 bedrooms, 3 beds, 1 bathroom
7–12 Oct
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Flat in Castelfalfi
The Francesca
1 bedroom, 1 king bed, 1 bathroom
7–12 Oct
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Top guest favourite
Home in Gambassi Terme
Il Fienile, Luxury Apartment in the Tuscan Hills
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 234 reviews
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Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 reviews
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Flat in Gambassi Terme
Casa Cosetta
1 bedroom, 2 beds, 1 bathroom
1–6 Jan
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Villa in Gambassi Terme
La Striscia Villa Farm with Private Pool
4 bedrooms, 6 beds, 3 bathrooms
6–11 Oct
5.0 out of 5 average rating, 3 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, 3 reviews
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Top guest favourite
Castle in Montaione
Villa Strozzi – Collegalli Estate
5 bedrooms, 8 beds, 4.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 44 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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Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 31 reviews
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Rooms in Barberino Val d'Elsa
Four-Poster Bed | Agriturismo with Pool | Chianti
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
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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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Room in Barberino Val d'Elsa
Compact Double | Chianti | Pool & Restaurant
1 double bed, 1 bathroom
4–9 Oct
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Top guest favourite
Apartment in San Gimignano
"HOME SWEET HOME" appartamento a San Gimignano
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 53 reviews
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Guest favourite
Flat in San Gimignano
Farmhouse in Valle Mora
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
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