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Search results; Over 1,000 homes in Poggibonsi

Top guest favourite
Flat in Poggibonsi
Apartment in Tuscany with giant oak tree
1 bedroom, 3 beds, 1 private bathroom
11–16 Oct
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4.98 out of 5 average rating, 64 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
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
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
Laura Chianti Holidays
2 bedrooms, 5 beds
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!
2 bedrooms, 2 beds
11–16 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Poggibonsi
cate house
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 7 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
Apartment in Poggibonsi
Casa Amaryllis
1 bedroom, 1 double bed
10–15 Oct
4.98 out of 5 average rating, 289 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, 130 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
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
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
Flat in San Gimignano
Herons Superior Apartment - Splendid view!
2 bedrooms, 2 double beds
26–31 Oct
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Flat in Poggibonsi
App. Poggiarello
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Home in Colle di Val d'Elsa
The House in the Alley – Colle di Val d'Elsa
2 bedrooms, 3 beds
5–10 Nov
4.99 out of 5 average rating, 134 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds
18–23 Sept
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds
2–7 Nov
5.0 out of 5 average rating, 27 reviews