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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
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
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
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
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
Villa Bonelli - La Magnolia Apartment
Individual host
3–8 Oct
4.94 out of 5 average rating, 143 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
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
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
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
Individual host
6–11 Oct
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Flat in Siena
CASA WOW panoramic terrace * . *
Individual host
21–26 Sept
4.98 out of 5 average rating, 107 reviews
Top guest favourite
Apartment in Siena
NEW in Siena, Porta Ovile + free private parking
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 121 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