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Search results; Over 1,000 homes in Poggibonsi

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Guest favourite
Holiday home in Poggibonsi
App.Cavallo - Megognano,2/A
1 bedroom, 3 beds, 2 shared bathrooms
21–26 Sept
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4.9 out of 5 average rating, 77 reviews
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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
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Top guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
2 bedrooms, 5 beds, 1 bathroom
19–24 Sept
4.95 out of 5 average rating, 151 reviews
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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, 97 reviews
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Guest favourite
Flat in Poggibonsi
Cozy tourist house for 4 guests, top relaxation!
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 8 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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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, 337 reviews
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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
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Guest favourite
Flat in Poggibonsi
cate house
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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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
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Top guest favourite
Flat in Poggibonsi
Modern and bright studio apartment! New!
1 bedroom, 1 double bed, 1 bathroom
7–12 Oct
5.0 out of 5 average rating, 17 reviews
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Superhost
Home in Poggibonsi
Villa Mocarello "IL CIPRESSO"
1 bedroom, 1 double bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Holiday home in Poggibonsi
Podere Chiocciola, 2 bedroom apartment
2 bedrooms, 2 double beds, 1.5 bathrooms
1–6 Sept
4.85 out of 5 average rating, 46 reviews
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Top guest favourite
Apartment in Poggibonsi
Casa Amaryllis
1 bedroom, 1 double bed, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 288 reviews
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Guest favourite
Apartment in San Gimignano
Casolare apartment with pool “Casa Monti”
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 11 reviews
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Home in Colle di Val d'Elsa
La Malpensata | View & Relax [Chianti & Siena]
1 bedroom, 1 double bed, 1 bathroom
1–6 Sept
New place to stay
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Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 27 reviews
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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, 385 reviews