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Search results; Over 1,000 homes in Siena

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Top guest favourite
Loft in Siena
Siena Country Loft Hideway
1 bedroom, 1 bed, 2 bathrooms
12–17 Oct, Individual host
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4.95 out of 5 average rating, 255 reviews
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Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 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, 21 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, 17 reviews
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Top guest favourite
Villa in Greve in Chianti
Medieval castle (27 beds)-Chianti-Florence 15km
Business host
1–6 Oct
4.99 out of 5 average rating, 74 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 reviews
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Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
8–13 Dec
5.0 out of 5 average rating, 108 reviews
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Guest favourite
Villa in Sovicille
Farmhouse Podere Il Moro in the nature of Siena
Business host
16–21 Sept
4.95 out of 5 average rating, 20 reviews
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Guest favourite
Villa in Siena
Elf's Hut - Elf's Hut
Business host
26 Sept – 1 Oct
4.97 out of 5 average rating, 60 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, 15 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
Business host
19–24 Oct
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
8–13 Oct
4.99 out of 5 average rating, 151 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, 446 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 reviews
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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Business host
30 Oct – 4 Nov
4.99 out of 5 average rating, 116 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 389 reviews