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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
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
Top guest favourite
Flat in Asciano
Belvedere apartment in farmhouse with swimming pool
4.97 out of 5 average rating, 79 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Oct
Guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
4.99 out of 5 average rating, 146 reviews, 5 bedrooms, 6 beds, 4 bathrooms
8–13 Oct
Top guest favourite
Holiday home in San Gimignano
Tuscan House with Private Jacuzzi in Chianti
4.94 out of 5 average rating, 85 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Aug
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
4.98 out of 5 average rating, 46 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
Guest favourite
Villa in Siena
Elf's Hut - Elf's Hut
4.97 out of 5 average rating, 58 reviews, 4 bedrooms, 4 beds, 4 bathrooms
1–6 Aug
Superhost
Home in Barberino Tavarnelle
Exclusive Villa with Pool in Chianti Classico
5 bedrooms, 5 beds, 6 bathrooms
2–7 Aug
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
5.0 out of 5 average rating, 50 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
Top guest favourite
Home in Siena
the chestnut house
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Oct
Top guest favourite
Apartment in Siena
GuestHost - Stunning Church of San Domenico View
4.95 out of 5 average rating, 58 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4.98 out of 5 average rating, 46 reviews, 4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 4 bathrooms
24–29 Aug
Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
4.84 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Room in Gaiole in Chianti
Argentina. Welcome to our small village, L...
4.94 out of 5 average rating, 18 reviews, 2 beds, 1 bathroom
4–9 Oct
Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
4.97 out of 5 average rating, 70 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
19–24 Oct