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Search results; Over 1,000 homes in Poggibonsi

Guest favourite
Holiday home in Poggibonsi
Vittoria Chianti Vacations 🍇🍷
2 bedrooms, 4 beds, 1 private bathroom
14–19 Nov, Individual host
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4.94 out of 5 average rating, 205 reviews
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
Guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
Individual host
11–16 Oct
4.95 out of 5 average rating, 152 reviews
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
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
31 Oct – 7 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Apartment in Poggibonsi
Casa Amaryllis
Individual host
10–15 Oct
4.98 out of 5 average rating, 290 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
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, 49 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
21–26 Sept
5.0 out of 5 average rating, 131 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 339 reviews
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, 8 reviews
Guest favourite
Flat in Poggibonsi
cate house
Individual host
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 386 reviews
Top guest favourite
Holiday home in Poggibonsi
Podere Chiocciola, 2 bedroom apartment
Individual host
23–28 Sept
4.85 out of 5 average rating, 47 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
Business host
16–21 Apr
4.95 out of 5 average rating, 22 reviews
Flat in Poggibonsi
small apartment 90 metres from Siena Eye Laser
Individual host
13–18 Sept
New place to stay
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
Individual host
2–7 Nov
5.0 out of 5 average rating, 27 reviews
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, 134 reviews