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Search results; Over 1,000 homes in Simignano

Top guest favourite
Home in Simignano
Casa al Gianni - The Simignano Barn
5 bedrooms, 5 beds, 4 private bathrooms
31 Oct – 5 Nov, Business host
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4.97 out of 5 average rating, 198 reviews
Top guest favourite
Farm stay in Simignano
Casa al Gianni - Fig
Business host
21–26 Oct
4.92 out of 5 average rating, 289 reviews
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
10–15 Oct
4.99 out of 5 average rating, 85 reviews
Superhost
Holiday home in Sovicille
Exclusive Use TrueTuscanFarm PoolHottubAC Siena20P
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Apartment in Sovicille
Spacious home in Tuscan countryside 10min to Siena
Individual host
23–29 Sept
4.94 out of 5 average rating, 177 reviews
Villa in Radicondoli
Villa Le Bolli, a holiday to be loved
Business host
2–7 Nov
Top guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 17 reviews
Guest favourite
Farm stay in Sovicille
Tuscan Villa: Pool, Hot Tub, 4bd, A/C, Wi-Fi, Siena
Business host
21–26 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
16–21 Sept
4.92 out of 5 average rating, 389 reviews
Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
Individual host
27 Oct – 1 Nov
5.0 out of 5 average rating, 29 reviews
Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
Individual host
9–14 Oct
4.96 out of 5 average rating, 149 reviews
Guest favourite
Home in Monteriggioni
Next to castle of Villa-Siena. heart Francigena
Individual host
20–25 Sept
4.83 out of 5 average rating, 157 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
Individual host
30 Oct – 4 Nov
4.99 out of 5 average rating, 472 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Home in Poggiolo
Country House Podere l 'Assunta
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 90 reviews