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Search results; Over 1,000 homes in Poggibonsi

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Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
Business host
19–24 Oct
4.97 out of 5 average rating, 72 reviews
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Guest favourite
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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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, 100 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
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 389 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Poggibonsi
La Casa di Chloe - apartment
Individual host
22–27 May
5.0 out of 5 average rating, 15 reviews
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Flat in Poggibonsi
small apartment 90 metres from Siena Eye Laser
Individual host
16–21 Sept
New place to stay
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Top guest favourite
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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
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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Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 342 reviews
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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
11–16 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
Individual host
8–13 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Villa in Greve in Chianti
Medieval castle (27 beds)-Chianti-Florence 15km
Business host
1–6 Oct
4.99 out of 5 average rating, 74 reviews
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Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
Individual host
27 Oct – 1 Nov
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Colle di Val d'Elsa
The House in the Alley – Colle di Val d'Elsa
Individual host
5–10 Nov
4.99 out of 5 average rating, 135 reviews