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Search results; Over 1,000 homes in Siena

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Top guest favourite
Farm stay in Siena
Authentic Tuscan Country House WITH A/C
1 bedroom, 1 bed, 2 private bathrooms
10–15 Oct, Business host
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4.97 out of 5 average rating, 325 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, 16 reviews
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Top guest favourite
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
Villa in Impruneta
Private Estate - Personal Concierge & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 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, 113 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 Greve in Chianti
Farmhouse with pool in Chianti
Business host
17–22 Nov
4.98 out of 5 average rating, 444 reviews
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Top guest favourite
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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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
1–6 Sept
5.0 out of 5 average rating, 4 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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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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
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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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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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, 149 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 Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
19–26 Sept
5.0 out of 5 average rating, 10 reviews