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Search results; Over 1,000 homes in Siena

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Top guest favourite
Flat in Siena
The rooftop terrace
2 bedrooms, 3 beds, 1 private bathroom
18–23 Oct, Individual host
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4.95 out of 5 average rating, 424 reviews
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Top guest favourite
Flat in Siena
Diacceto19 Siena Apartments Int.1
Individual host
20–25 Nov
4.98 out of 5 average rating, 440 reviews
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Top guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
Individual host
2–7 Nov
5.0 out of 5 average rating, 97 reviews
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Top guest favourite
Villa in Impruneta
Private Estate - Personal Concierge & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 144 reviews
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Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
30 Nov – 5 Dec
5.0 out of 5 average rating, 104 reviews
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Superhost
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 112 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
19–24 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Farmhouse with pool in Chianti
Business host
17–22 Nov
4.98 out of 5 average rating, 443 reviews
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Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
12–17 Oct
5.0 out of 5 average rating, 40 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
5–10 Sept
New place to stay
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Superhost
Room in Gaiole in Chianti
Argentina. Welcome to our little village, L...
Business host
14–19 Oct
4.95 out of 5 average rating, 20 reviews
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Superhost
Apartment in Siena
Luxury penthouse with a view of Piazza del Campo
Individual host
25–30 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
22–27 Sept
4.99 out of 5 average rating, 148 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
Business host
1–6 Nov
4.84 out of 5 average rating, 109 reviews
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Home in Siena
Siena Centre Luxury Design TownHouse -Parking Near
Individual host
9–14 Sept
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Flat in Siena
Villa Bonelli - La Magnolia Apartment
Individual host
3–8 Oct
4.94 out of 5 average rating, 142 reviews