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Search results; Over 1,000 homes in Poggibonsi

Top guest favourite
Flat in Poggibonsi
Il Casale di Villore, Poggibonsi, Siena, Tuscany, Morellino Apt.
1 bedroom, 1 bed, 1 private bathroom
16–21 Oct, Business host
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4.96 out of 5 average rating, 80 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
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
Guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
Individual host
14–19 Nov
4.95 out of 5 average rating, 152 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, 51 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
16–21 Sept
4.92 out of 5 average rating, 389 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
8–13 Oct
5.0 out of 5 average rating, 131 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 209 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
Business host
16–21 Apr
4.96 out of 5 average rating, 23 reviews
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, 60 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 Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 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
Flat in Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 340 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews