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Search results; Over 1,000 homes in Asciano

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Superhost
Home in Asciano
Family Forest - Pool in the Crete Senesi
2 bedrooms, 4 beds, 2 private bathrooms
2–7 Nov
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4.91 out of 5 average rating, 85 reviews
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Top guest favourite
Flat in Asciano
In_Bangaia
1 bedroom, 1 double bed, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 21 reviews
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Flat in Asciano
"La Quercia" Apartment in a historic Tuscan farmhouse
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Home in Asciano
"Le Arcate" apartment in an 18th-century farmhouse
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
5 bedrooms, 5 double beds, 5.5 bathrooms
18–23 Nov
4.98 out of 5 average rating, 115 reviews
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Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Flat in Lucignano
Palazzo Trapani Luxury Residence
2 bedrooms, 1 bed, 2.5 bathrooms
13–18 Nov
5.0 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Montalcino
Villa Cipressino
4 bedrooms, 5 beds, 5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 12 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
4 bedrooms, 6 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Apartment in San Quirico d'Orcia
Panoramic Apartment in Center Dimora del Poggio
2 bedrooms, 2 double beds, 1 bathroom
1–6 Jan
4.99 out of 5 average rating, 99 reviews
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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, 16 reviews
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Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
2 bedrooms, 6 beds, 3 bathrooms
22–27 Sept
4.99 out of 5 average rating, 76 reviews
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Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
3 bedrooms, 4 beds, 3 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 reviews
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Top guest favourite
Apartment in Pienza
Tuscan country house at Mascagni Farmhouse in Pienza
2 bedrooms, 2 double beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 158 reviews
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Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
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Superhost
Flat in Montalcino
Wp Relais Argante Apartment
3 bedrooms, 4 beds, 3 bathrooms
25–30 Sept
5.0 out of 5 average rating, 4 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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Top guest favourite
Flat in Lucignano
Apartament Lucignano Window
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Nov
5.0 out of 5 average rating, 85 reviews
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Guest favourite
Flat in Rapolano Terme
The House in the Hamlet
1 bedroom, 1 double bed, 1 bathroom
7–12 Oct
5.0 out of 5 average rating, 9 reviews