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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
4–9 Sept
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4.93 out of 5 average rating, 191 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
6–11 Oct
4.96 out of 5 average rating, 148 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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
1–6 Sept
New place to stay
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Guest favourite
Apartment in Casole d'Elsa
Apartment with Pool near Siena
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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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
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Home in Poggiolo
Country House Podere l 'Assunta
2 bedrooms, 4 beds, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 88 reviews
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Superhost
Farm stay in Sovicille
Tuscan Villa: Pool, Hot Tub, 4bd, A/C, Wi-Fi, Siena
4 bedrooms, 8 beds, 7.5 bathrooms
21–26 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Castel San Gimignano
Elegant private cottage Volterra–San Gimignano
1 bedroom, 2 beds, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 3 reviews
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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, 15 reviews
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Top guest favourite
Farm stay in Siena
Authentic Tuscan Country House WITH A/C
1 bedroom, 1 double bed, 2 bathrooms
10–15 Oct
4.97 out of 5 average rating, 325 reviews
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Farm stay in Monteriggioni
Podere Casalino - Il Gatto
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.9 out of 5 average rating, 115 reviews
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Flat in Siena
apartment with a view in a farmhouse in Siena with Wi-Fi
2 bedrooms, 2 double beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 11 reviews
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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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Flat in Siena
San Francesco Penthouse
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 87 reviews
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Flat in Siena
Charm and Comfort
3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 43 reviews
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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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Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 337 reviews