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Guest favourite
Cottage in Ponte Feccia
Country cottage C&M surrounded by greenery, love Tuscany
1 bedroom, 3 beds, 1 private bathroom
1–6 Oct, Individual host
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4.94 out of 5 average rating, 203 reviews
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Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
21–26 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
10–15 Oct
4.99 out of 5 average rating, 85 reviews
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Guest favourite
Villa in Monterotondo Marittimo
Il Poderino Guest House
Business host
26 Sept – 3 Oct
5.0 out of 5 average rating, 7 reviews
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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
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Top guest favourite
Holiday home in Monteroni d'Arbia
Tuja
Business host
22–27 Oct
5.0 out of 5 average rating, 35 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Top guest favourite
Farm stay in Simignano
Casa al Gianni - Hut
Business host
12–17 Nov
4.93 out of 5 average rating, 292 reviews
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Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
13–18 Nov
4.97 out of 5 average rating, 116 reviews
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Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 reviews
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Top guest favourite
Home in Chiusdino
La Capanna: country house with magnificent view
Individual host
3–8 Oct
4.92 out of 5 average rating, 85 reviews
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Top guest favourite
Flat in Colle di Val d'Elsa
CANONICA 43 Luxury villa in the heart of Tuscany
Individual host
13–18 Oct
5.0 out of 5 average rating, 80 reviews
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Guest favourite
Villa in Siena
Elf's Hut - Elf's Hut
Business host
26 Sept – 1 Oct
4.97 out of 5 average rating, 60 reviews
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Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
17–22 Sept
4.99 out of 5 average rating, 138 reviews
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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
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Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 209 reviews
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Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 reviews
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Top guest favourite
Apartment in Siena
Luxury penthouse with a view of Piazza del Campo
Individual host
25–30 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
Individual host
18–23 Oct
4.98 out of 5 average rating, 65 reviews