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Search results; Over 1,000 homes

Top guest favourite
Farm stay in Siena
La Villa Farmhouse - Chestnut, Pool & Garden
3 bedrooms, 7 beds, 3 private bathrooms
21–26 Sept, Business host
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4.98 out of 5 average rating, 220 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
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
Villa in Siena
Virgi House
Individual host
12–17 Oct
4.98 out of 5 average rating, 215 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, 106 reviews
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
Exclusive Villa Mami
Business host
18–23 Oct
5.0 out of 5 average rating, 25 reviews
Apartment in Siena
Siena Centre – Modern Apartment with Parking
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 4 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
Farm stay in Siena
Typical Tuscan Country House WITH A/C
Business host
12–17 Oct
4.98 out of 5 average rating, 291 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
Flat in Siena
Villa Bonelli - La Magnolia Apartment
Individual host
3–8 Oct
4.94 out of 5 average rating, 143 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, 55 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 Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Siena
Siena Centre Luxury Design TownHouse -Parking Near
Individual host
9–14 Sept
5.0 out of 5 average rating, 17 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
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