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Search results; Over 1,000 homes in Ancaiano

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Top guest favourite
Serviced apartment in Ancaiano
Tower house in the countryside with sensory shower
1 bedroom, 2 beds, 2 private bathrooms
10–15 Nov
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4.98 out of 5 average rating, 119 reviews
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Farm stay in Simignano
Casa al Gianni - Hut
1 bedroom, 1 double bed, 1 bathroom
22–27 Nov
4.93 out of 5 average rating, 294 reviews
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Home in Simignano
Casa al Gianni - The Simignano Barn
5 bedrooms, 5 beds, 4 bathrooms
16–21 Nov
4.97 out of 5 average rating, 199 reviews
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Home in Siena
Secret Garden Siena
3 bedrooms, 3 beds, 2 bathrooms
2–7 Nov
4.98 out of 5 average rating, 222 reviews
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Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 23 reviews
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Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds, 3 bathrooms
6–11 Oct
4.98 out of 5 average rating, 218 reviews
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Home in Pievescola
La Casa di Gio - Toscana a 360°
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
New place to stay
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Superhost
Flat in Sovicille
Medieval castle living: 20m swimming pool , vineya
6 bedrooms, 9 beds, 6 bathrooms
17–22 May
5.0 out of 5 average rating, 3 reviews
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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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Room in Castelnuovo Berardenga
Tuscan Hideaway at Le Pietre Vive, Room with a .
1 bed, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 35 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, 4 reviews
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Home in Ponte allo Spino
Dolce Domi
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 6 reviews
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Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 61 reviews
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Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms, 2 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 34 reviews
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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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Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms, 4 beds, 2 bathrooms
21–26 Oct
4.95 out of 5 average rating, 42 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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Home in Siena
Domus Nannini - Loggia Salimbeni SPA
3 bedrooms, 4 beds, 3.5 bathrooms
15–20 Nov
4.96 out of 5 average rating, 156 reviews
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Castle in Poggibonsi
Castello Di Badia – Panoramic Pool Overlooking Tuscany
5 bedrooms, 6 beds, 5.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 72 reviews