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Search results; Over 1,000 homes

Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Home in Siena
Fabulous house on Campo with a guest house.
Individual host
25–30 Sept
4.98 out of 5 average rating, 63 reviews
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, 105 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, 20 reviews
Top guest favourite
Farm stay in Siena
Typical Tuscan Country House WITH A/C
Business host
12–17 Oct
4.98 out of 5 average rating, 290 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
Top guest favourite
Villa in Siena
Virgi House
Individual host
12–17 Oct
4.98 out of 5 average rating, 214 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
Holiday home in Sovicille
Podere La Castellina - No. 4 FICO
Business host
17–22 Oct
4.96 out of 5 average rating, 109 reviews
Apartment in Siena
Siena Centre – Modern Apartment with Parking
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Siena
Villa Bonelli - La Magnolia Apartment
Individual host
26–31 Oct
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Guest suite in Siena
Fonte Giusta, romantic suite with breathtaking views
Individual host
4–9 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Siena
San Francesco Penthouse
Individual host
26–31 Oct
4.98 out of 5 average rating, 88 reviews
Guest favourite
Flat in San Gusmè
La Dimora del Luca
Individual host
8–13 Nov
4.98 out of 5 average rating, 169 reviews
Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
Individual host
6–11 Oct
5.0 out of 5 average rating, 96 reviews