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Search results; Over 1,000 homes in Villa a Sesta

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Guest favourite
Home in Villa A Sesta
Casa Matilde Chianti - Jeky Stay
2 bedrooms, 2 beds, 1.5 private bathrooms
8–13 Oct
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4.92 out of 5 average rating, 63 reviews
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Top guest favourite
Cottage in Villa A Sesta
CASA MARIA
2 bedrooms, 3 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Villa in Villa A Sesta
Private villa with pool
4 bedrooms, 4 double beds, 2 bathrooms
24 Sept – 1 Oct
4.83 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Villa A Sesta
Raffaella's House in Chianti
2 bedrooms, 3 beds, 1 bathroom
28 Oct – 2 Nov
4.99 out of 5 average rating, 481 reviews
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Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 472 reviews
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Guest favourite
Flat in San Gusmè
La Dimora del Luca
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 171 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 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
Home in Troghi
Historic residence 30 minutes from Florence
2 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 90 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 56 reviews
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Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 342 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
New place to stay
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Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds, 2 bathrooms
2–7 Jan
5.0 out of 5 average rating, 109 reviews
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Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
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Top guest favourite
Home in Bellavista
Bellavista, entire Tuscan villa for exclusive use
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 11 reviews
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Superhost
Home in Castelnuovo Berardenga
Camere in Bed and Breakfast Casa Cernano
2 bedrooms, 2 beds, 2 bathrooms
5–10 Oct
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Top guest favourite
Home in Siena
Siena Centre Luxury Design TownHouse -Parking Near
2 bedrooms, 2 double beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
2 bedrooms, 6 beds, 3 bathrooms
22–27 Sept
4.99 out of 5 average rating, 78 reviews