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Search results; Over 1,000 homes

Guest favourite
Cottage in Siena
Wonderful Villa for 10 people in Valdorcia
5 bedrooms, 5 beds, 5 private bathrooms
2–7 Apr, Business host
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4.95 out of 5 average rating, 57 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
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
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
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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
Guest favourite
Apartment in Siena
Siena Centre – Modern Apartment with Parking
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Siena
Fabulous house on Campo with a guest house.
Individual host
1–6 Oct
4.98 out of 5 average rating, 63 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, 293 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
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
Guest favourite
Flat in San Gusmè
La Dimora del Luca
Individual host
8–13 Nov
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Flat in Siena
Il Mezzanino
Business host
13–18 Oct
4.97 out of 5 average rating, 34 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
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 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, 56 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