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Search results; Over 1,000 homes in Poggio San Marco

Guest favourite
Home in Poggio San Marco
Charming converted Hayloft overlooking the Chianti Hills
2 bedrooms, 2 beds, 1 shared bathroom
25–30 Sept, Individual host
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4.97 out of 5 average rating, 307 reviews
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
19–24 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Farm stay in Cavriglia
La Ginestra – Former Tuscan barn over two levels
Business host
1–6 Nov
5.0 out of 5 average rating, 8 reviews
Superhost
Flat in Cavriglia
Basil – Simplicity and relaxation in Tuscany
Business host
4–9 Oct
Superhost
Flat in Cavriglia
Il Ginepro – Relaxation with a Pool View in Chianti
Business host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
15–20 Sept
New place to stay
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 Bucine
Villa Tontenano Capannole Chianti private pool 12
Business host
10–17 Oct
4.98 out of 5 average rating, 60 reviews
Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
Business host
16–21 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Villa in Castel Focognano
Villa Marinelli: pool, hot tub & garden, Tuscany
Individual host
14–19 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Villa in Modine
Tuscan Villa with Private Jacuzzi & River
Business host
30 Oct – 4 Nov
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
Individual host
24–29 Oct
5.0 out of 5 average rating, 19 reviews
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
Business host
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 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
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
Business host
20–25 Sept
5.0 out of 5 average rating, 26 reviews