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Search results; Over 1,000 homes in Siena

Top guest favourite
Home in Il Poggetto
The Loggia
2 bedrooms, 3 beds, 2 private bathrooms
21–26 Oct, Individual host
,
4.93 out of 5 average rating, 153 reviews
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
10–15 Oct
4.99 out of 5 average rating, 85 reviews
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
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
Individual host
25 Sept – 2 Oct
4.99 out of 5 average rating, 75 reviews
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
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
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
Top guest favourite
Home in Siena
VILLA SIENA with pool and spa
Individual host
3–10 Oct
5.0 out of 5 average rating, 28 reviews
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
Top guest favourite
Apartment in Noce
Podere Vergianoni nestled in Chianti with a pool
Business host
11–16 Nov
5.0 out of 5 average rating, 351 reviews
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
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, 115 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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, 98 reviews
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, 151 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Farm stay in Greve in Chianti
Typical Tuscan country house
Business host
3–8 Dec
4.99 out of 5 average rating, 432 reviews
Top guest favourite
Villa in Siena
Virgi House
Individual host
12–17 Oct
4.98 out of 5 average rating, 215 reviews