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Search results; Over 1,000 homes in Poggibonsi

Guest favourite
Holiday home in Poggibonsi
App.Cavallo - Megognano,2/A
1 bedroom, 3 beds, 2 shared bathrooms
11–16 Oct
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4.9 out of 5 average rating, 77 reviews
Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
5 bedrooms, 6 beds, 5.5 bathrooms
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, 1 bathroom
11–16 Oct
4.95 out of 5 average rating, 151 reviews
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
3 bedrooms, 3 beds, 3.5 bathrooms
31 Oct – 7 Nov
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
3 bedrooms, 4 beds, 2 bathrooms
6–11 Nov
4.99 out of 5 average rating, 98 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 130 reviews
Top guest favourite
Room in Poggibonsi
Modern room in Poggibonsi: in the heart of Tuscany
1 queen bed, 1 bathroom
10–15 Sept
4.92 out of 5 average rating, 447 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
2 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 49 reviews
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 338 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Villa in Noce
Villa in Toscana con piscina privata panoramica
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 207 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 386 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 27 reviews