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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
Superhost
Home in Barberino Tavarnelle
Exclusive Villa with Pool in Chianti Classico
5 bedrooms, 5 beds, 6 bathrooms
2–7 Aug
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Flat in Asciano
Belvedere apartment in farmhouse with swimming pool
4.97 out of 5 average rating, 78 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Oct
Top 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 Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
4.99 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Nov
Top guest favourite
Farm stay in Greve in Chianti
Farmhouse with pool in Chianti
4.98 out of 5 average rating, 437 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 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
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
5.0 out of 5 average rating, 48 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
Superhost
Home in Gaiole in Chianti
Fienile House
New place to stay, 2 bedrooms, 2 beds, 2.5 bathrooms
21–26 Aug
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
4.99 out of 5 average rating, 144 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, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
26 Nov – 1 Dec
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
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
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
Farm stay in Siena
Typical Tuscan Country House WITH A/C
4.98 out of 5 average rating, 288 reviews, 1 bedroom, 1 bed, 2 bathrooms
12–17 Oct
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
Guest favourite
Flat in Siena
[NEW!] Renovated, just a stone's throw from the center!
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Aug