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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
30 Oct – 4 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
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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
19–24 Oct
4.98 out of 5 average rating, 217 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
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 208 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
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
21–26 Sept
5.0 out of 5 average rating, 130 reviews
Top guest favourite
Flat in Poggibonsi
Large Tuscan Chianti Tower suite Apartment
Business host
19–24 Oct
4.94 out of 5 average rating, 49 reviews
Guest favourite
Townhouse in Colle di Val d'Elsa
L'Arco
Business host
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in San Gimignano
Casaglia Residence
Individual host
5–10 Oct
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Villa in Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Apartment in Poggibonsi
Casa Amaryllis
Individual host
10–15 Oct
4.98 out of 5 average rating, 289 reviews
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 339 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
Business host
26 Apr – 1 May
4.95 out of 5 average rating, 22 reviews