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Search results; Over 1,000 homes in Poggibonsi

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Top guest favourite
Holiday home in Poggibonsi
Podere le Fonti - Pet Friendly - 15 min to San Gimignano
4 bedrooms, 4 beds, 3 private bathrooms
17–22 Sept
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4.97 out of 5 average rating, 39 reviews
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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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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
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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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
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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, 98 reviews
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Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 338 reviews
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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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Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 129 reviews
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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, 140 reviews
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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
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Top guest favourite
Villa in Noce
Historic villa with private pool in Tuscany
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 35 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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Superhost
Home in Barberino Tavarnelle
Exclusive Villa with Pool in Chianti Classico
5 bedrooms, 5 double beds, 6 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Villa in Tignano
Villa Isabella
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 207 reviews
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Home in Barberino Tavarnelle
Exclusive Villa Tegolato in Chianti
10 bedrooms, 11 beds, 8 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 53 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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Top guest favourite
Apartment in San Gimignano
Casaglia Residence
2 bedrooms, 4 beds, 1 bathroom
5–10 Oct
4.97 out of 5 average rating, 75 reviews