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Search results; Over 1,000 homes in Poggibonsi

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Guest favourite
Holiday home in Poggibonsi
Il Casale di Villore, Poggibonsi, Siena, Tuscany, Cardisco Apt.
2 bedrooms, 2 beds, 1 private bathroom
24–29 Oct, Business host
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4.92 out of 5 average rating, 66 reviews
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Top guest favourite
Castle in Poggibonsi
Castello Di Badia - panoramic pool overlooking Tuscany
Business host
19–24 Oct
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
Individual host
6–11 Nov
4.99 out of 5 average rating, 101 reviews
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Apartment in Poggibonsi
Gallery Apartment near Chianti
Individual host
14–19 Nov
4.95 out of 5 average rating, 153 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
15–20 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 389 reviews
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Apartment in Poggibonsi
Casa Amaryllis
Individual host
10–15 Oct
4.98 out of 5 average rating, 290 reviews
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Flat in Poggibonsi
Laura Chianti Holidays
Individual host
19–24 Nov
4.98 out of 5 average rating, 342 reviews
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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
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Flat in Poggibonsi
small apartment 90 metres from Siena Eye Laser
Individual host
3–8 Oct
New place to stay
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Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
8–13 Oct
5.0 out of 5 average rating, 131 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
New place to stay
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Guest favourite
Flat in Poggibonsi
cate house
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Flat in Poggibonsi
Cozy tourist house for 4 guests, top relaxation!
Individual host
16–21 Oct
5.0 out of 5 average rating, 9 reviews
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Flat in Poggibonsi
App.Falegnameria
Business host
27 Sept – 2 Oct
4.97 out of 5 average rating, 62 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
18–23 Sept
4.98 out of 5 average rating, 61 reviews
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Top guest favourite
Apartment in San Gimignano
AnticaVista, Luxury Apartment with Tower Views
Individual host
1–6 Nov
5.0 out of 5 average rating, 69 reviews