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Search results; Over 1,000 homes in Poggibonsi

Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 private bathrooms
10–15 Oct
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4.98 out of 5 average rating, 47 reviews
Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
5 bedrooms, 6 beds
19–24 Oct
4.97 out of 5 average rating, 72 reviews
Guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
2 bedrooms, 5 beds
11–16 Oct
4.95 out of 5 average rating, 152 reviews
Top guest favourite
Room in Poggibonsi
Ensuite room between Siena and Florence
1 queen bed
11–16 Oct
4.95 out of 5 average rating, 579 reviews
Flat in Poggibonsi
Small apartment 90 meters from Siena Eye Laser
1 bedroom, 1 double bed
13–18 Sept
New place to stay
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
3 bedrooms, 3 beds
31 Oct – 7 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed
21–26 Sept
5.0 out of 5 average rating, 131 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
15–20 Sept
New place to stay
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds
9–14 Nov
4.98 out of 5 average rating, 340 reviews
Top guest favourite
Apartment in Poggibonsi
Casa Amaryllis
1 bedroom, 1 double bed
10–15 Oct
4.98 out of 5 average rating, 290 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
2 bedrooms, 3 beds
27 Oct – 1 Nov
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
3 bedrooms, 4 beds
6–11 Nov
4.99 out of 5 average rating, 100 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds
30 Oct – 4 Nov
4.92 out of 5 average rating, 386 reviews
Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
2 bedrooms, 3 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
2 bedrooms, 2 double beds
16–21 Apr
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds
19–24 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds
21–26 Nov
5.0 out of 5 average rating, 54 reviews