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

Superhost
Apartment in San Polo in Chianti
Il Conventino Amazing 19th Cent. Tuscan Farmhouse
1 bedroom, 2 beds, 1 shared bathroom
14–19 Sept, Individual host
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4.9 out of 5 average rating, 111 reviews
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, 282 reviews
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
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
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
12–17 Sept
New place to stay
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
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 reviews
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
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Guest favourite
Apartment in Bagno A Ripoli
Historic Florentine Villa Apartment With Pool
Individual host
12–19 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 reviews
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
13–18 Sept
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
24–29 Sept
5.0 out of 5 average rating, 8 reviews
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, 48 reviews
Featured hotel
Room in Bagno A Ripoli
Quadruple room
Business host
2–7 Oct
New place to stay