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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
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
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
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
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
Home in Siena
Siena Centre Luxury Design TownHouse -Parking Near
Individual host
16–21 Sept
5.0 out of 5 average rating, 18 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Apartment in Siena
Casa Manori - refined and cozy two-room apartment
Individual host
15–20 Oct
4.99 out of 5 average rating, 102 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
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Siena
Exclusive Villa Mami
Business host
18–23 Oct
5.0 out of 5 average rating, 25 reviews
Guest favourite
Holiday home in Montebenichi
Agriturismo I Moraioli, Cantina apartment
Business host
13–18 Nov
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Siena
Palazzo del Taja - in the center with whirlpool
Individual host
23–28 Nov
4.99 out of 5 average rating, 254 reviews
Flat in Siena
Modern Central Penthouse with Panoramic Terrace
Individual host
21–26 Sept
New place to stay
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 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