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Search results; Over 1,000 homes in Poggibonsi

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Top guest favourite
Home in Poggibonsi
Casetta nel Chianti – Poggio di Villore
2 bedrooms, 3 beds, 2 private bathrooms
1–6 Oct
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4.97 out of 5 average rating, 30 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
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Apartment in Poggibonsi
Gallery Apartment near Chianti
2 bedrooms, 5 beds, 1 bathroom
14–19 Nov
4.95 out of 5 average rating, 153 reviews
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Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
3 bedrooms, 4 beds, 2 bathrooms
6–11 Nov
4.99 out of 5 average rating, 100 reviews
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Flat in Poggibonsi
Small apartment 90 meters from Siena Eye Laser
1 bedroom, 1 double bed, 1 bathroom
23–28 Sept
New place to stay
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Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
3 bedrooms, 3 beds, 3.5 bathrooms
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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Room in Poggibonsi
Modern room in Poggibonsi: in the heart of Tuscany
1 queen bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 447 reviews
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Flat in Poggibonsi
In the center of Tuscany
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.93 out of 5 average rating, 251 reviews
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Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
19–24 Nov
4.98 out of 5 average rating, 342 reviews
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Flat in Poggibonsi
cate house
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 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
New place to stay
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Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 131 reviews
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Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Poggibonsi
Cozy tourist house for 4 guests, top relaxation!
2 bedrooms, 2 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 9 reviews
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Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
2 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 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, 389 reviews
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Flat in Poggibonsi
La Casa di Chloe - apartment
3 bedrooms, 3 double beds, 3 bathrooms
22–27 May
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.98 out of 5 average rating, 47 reviews
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Flat in Poggibonsi
Little Moka in Tuscany
1 bedroom, 2 beds, 1 bathroom
3–8 Oct
New place to stay