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Search results; Over 1,000 homes in San Polo in Chianti

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Superhost
Apartment in San Polo in Chianti
Il Conventino Amazing 19th Cent. Tuscan Farmhouse
1 bedroom, 2 beds, 1 shared bathroom
19–24 Sept, Individual host
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4.9 out of 5 average rating, 111 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Ancient Tuscan farmhouse in the Chianti hills
Business host
21–26 Nov
4.99 out of 5 average rating, 284 reviews
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Superhost
Home in Greve in Chianti
Villa with swimming pool in the heart of Chianti | Florence
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
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Top guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
Business host
24–29 Sept
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
24–29 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Villa in Rignano sull'Arno
​Villa Fonticina: Private Pool & Secluded Woods
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Greve in Chianti
BEAUTIFUL OLD BARN IN CHIANTI
Individual host
24–29 Oct
4.99 out of 5 average rating, 142 reviews
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Top guest favourite
Flat in Pelago
Tuscan vineyard home. Near Florence
Individual host
10–17 Oct
5.0 out of 5 average rating, 73 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 reviews
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Superhost
Home in Figline e Incisa Valdarno
[Madu’s Country House Cerchiaia] Tuscany Pool
Individual host
9–14 Oct
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Top guest favourite
Home in Pontassieve
La Quercia House in the countryside
Individual host
9–14 Oct
5.0 out of 5 average rating, 67 reviews
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Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
Individual host
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Tiny home in Bagno A Ripoli
The Casetta di Montisoni
Individual host
11–16 Oct
5.0 out of 5 average rating, 81 reviews
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Top guest favourite
Apartment in Figline e Incisa Valdarno
[Beatrice's Dream] Luxury & Design Penthouse 5*
Individual host
9–14 Oct
4.98 out of 5 average rating, 89 reviews
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Top guest favourite
Farm stay in Impruneta
"Nocino Apartment" - Farmhouse - Chianti
Business host
4–9 Oct
5.0 out of 5 average rating, 129 reviews
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Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
17–22 Sept
New place to stay
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Guest favourite
Apartment in Bagno A Ripoli
Historic Florentine Villa Apartment With Pool
Individual host
17–24 Sept
4.97 out of 5 average rating, 36 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
New place to stay