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Guest favourite
Cottage in Massa Sabbioni
Private Country House with swimming pool -Chianti
5 bedrooms, 5 beds, 5.5 private bathrooms
27 Sept – 2 Oct
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4.95 out of 5 average rating, 57 reviews
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Guest favourite
Villa in Castelnuovo dei Sabbioni
Villa Valdarno Chianti - Private Pool
8 bedrooms, 12 beds, 7.5 bathrooms
26 Jun – 1 Jul
4.92 out of 5 average rating, 36 reviews
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Guest favourite
Holiday home in Cavriglia
Casa Tregli
3 bedrooms, 4 beds, 1 bathroom
21–27 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
6 bedrooms, 6 beds, 7 bathrooms
4–9 Oct
4.99 out of 5 average rating, 145 reviews
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Guest favourite
Home in Gaiole in Chianti
Exclusive private villa with private pool
6 bedrooms, 9 beds, 6 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Villa in Greve in Chianti
Villa Prenzano | A Rare Private Estate in Tuscany
6 bedrooms, 7 beds, 6.5 bathrooms
10–17 Oct
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Villa in Bucine
Villa Tontenano Capannole Chianti private pool 12
6 bedrooms, 8 beds, 7 bathrooms
10–17 Oct
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 1 bed, 5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Villa in Bucine
Villa Petrea - Holidays and Weddings
8 bedrooms, 14 beds, 8 bathrooms
24–31 Oct
4.94 out of 5 average rating, 90 reviews
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Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
6 bedrooms, 8 beds, 4.5 bathrooms
9–14 Oct
5.0 out of 5 average rating, 19 reviews
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Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
4 bedrooms, 4 king beds, 5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
3 bedrooms, 5 beds, 3 bathrooms
25–30 Sept
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds, 7 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 116 reviews
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 4 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Siena
San Francesco Penthouse
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 88 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Ancient Tuscan farmhouse in the Chianti hills
2 bedrooms, 2 double beds, 1 bathroom
23–28 Nov
4.99 out of 5 average rating, 284 reviews