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Search results; Over 1,000 homes in Simignano

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Guest favourite
Farm stay in Simignano
House at Gianni - Olmo
2 bedrooms, 2 beds, 1 private bathroom
3–8 Oct
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4.93 out of 5 average rating, 194 reviews
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Top guest favourite
Home in Simignano
Casa al Gianni - The Simignano Barn
5 bedrooms, 5 beds, 4 bathrooms
31 Oct – 5 Nov
4.97 out of 5 average rating, 198 reviews
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Guest favourite
Farm stay in Sovicille
House at Gianni - Leccio
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.92 out of 5 average rating, 232 reviews
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Top guest favourite
Farm stay in Sovicille
Agriturismo La Villa - Il Ciliegio, Pool & Garden.
2 bedrooms, 2 double beds, 1 bathroom
9–14 Oct
4.95 out of 5 average rating, 146 reviews
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Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
4.99 out of 5 average rating, 85 reviews
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Superhost
Holiday home in Sovicille
Exclusive Use TrueTuscanFarm PoolHottubAC Siena20P
8 bedrooms, 11 beds, 7 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds, 2 bathrooms
9–14 Oct
4.96 out of 5 average rating, 149 reviews
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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
27 Oct – 1 Nov
5.0 out of 5 average rating, 29 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, 389 reviews
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Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 342 reviews
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Guest favourite
Home in Monteriggioni
Next to castle of Villa-Siena. heart Francigena
4 bedrooms, 8 beds, 2 bathrooms
20–25 Sept
4.83 out of 5 average rating, 157 reviews
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Top guest favourite
Serviced apartment in Ancaiano
Tower house in the countryside with sensory shower
1 bedroom, 2 beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 119 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 55 reviews
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Guest favourite
Villa in Sovicille
Farmhouse Podere Il Moro in the nature of Siena
9 bedrooms, 16 beds, 9 bathrooms
16–21 Sept
4.95 out of 5 average rating, 20 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
New place to stay
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Top guest favourite
Farm stay in Monteroni d'Arbia
The Arches of Corsanello | Apt "Siena" x 3
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
4.97 out of 5 average rating, 77 reviews
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Home in Casole d'Elsa
Casa stella serena by geco vacation rentals
3 bedrooms, 4 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Apartment in Sovicille
Spacious home in Tuscan countryside 10min to Siena
4 bedrooms, 4 beds, 3 bathrooms
23–29 Sept
4.94 out of 5 average rating, 177 reviews
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 15 reviews