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Search results; Over 1,000 homes in Siena

Top guest favourite
Home in Il Poggetto
The Loggia
2 bedrooms, 2 beds, 2 private bathrooms
19–24 Aug
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4.93 out of 5 average rating, 150 reviews
Top guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Gaiole in Chianti
Fienile House
2 bedrooms, 2 double beds, 2.5 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Farm stay in Greve in Chianti
Typical Tuscan country house
2 bedrooms, 2 double beds, 2 bathrooms
7–12 Nov
4.99 out of 5 average rating, 428 reviews
Superhost
Home in Barberino Tavarnelle
Exclusive Villa with Pool in Chianti Classico
5 bedrooms, 5 double beds, 6 bathrooms
2–7 Aug
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Asciano
Belvedere apartment in farmhouse with swimming pool
3 bedrooms, 5 beds, 2 bathrooms
9–14 Oct
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Holiday home in San Gimignano
Tuscan House with Private Jacuzzi in Chianti
2 bedrooms, 2 double beds, 2 bathrooms
26 Nov – 1 Dec
4.94 out of 5 average rating, 83 reviews
Top guest favourite
Farm stay in Greve in Chianti
Farmhouse with pool in Chianti
2 bedrooms, 2 double beds, 2 bathrooms
17–22 Nov
4.98 out of 5 average rating, 437 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
5 bedrooms, 6 beds, 4 bathrooms
8–13 Oct
4.99 out of 5 average rating, 144 reviews
Top guest favourite
Farm stay in Greve in Chianti
Farmhouse in Chianti with Swimming Pool
2 bedrooms, 2 double beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 509 reviews
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 382 reviews
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, 332 reviews
Top guest favourite
Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
3 bedrooms, 4 beds, 2 bathrooms
6–11 Nov
4.99 out of 5 average rating, 93 reviews
Superhost
Flat in Scrofiano
Panoramic View New Apartment with Balcony and A/C
1 bedroom, 2 beds, 1 bathroom
20–25 Aug
New place to stay
Top guest favourite
Apartment in Siena
GuestHost - Stunning Church of San Domenico View
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.95 out of 5 average rating, 58 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 211 reviews