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Holiday home in Siena
San Giovan d'Asso - Apartment in Val d'Orcia
3 bedrooms, 6 beds, 2 shared bathrooms
11–16 Oct, Individual host
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4.77 out of 5 average rating, 13 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
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
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
8–13 Dec
5.0 out of 5 average rating, 107 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
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
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
Holiday home in Sovicille
Podere La Castellina - No. 4 FICO
Business host
17–22 Oct
4.96 out of 5 average rating, 109 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 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
Villa in Siena
Exclusive Villa Mami
Business host
18–23 Oct
5.0 out of 5 average rating, 25 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
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
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
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
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
Apartment in Pienza
Tuscan rural house in Mascagni Farmhouse Pienza
Business host
26–31 Oct
5.0 out of 5 average rating, 160 reviews
Top guest favourite
Flat in Siena
La casa in Camollia - Historic centre of Siena
Individual host
29 Oct – 3 Nov
4.95 out of 5 average rating, 105 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