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Search results; Over 1,000 homes in Siena

Guest favourite
Villa in Siena
L'Apparita del Peruzzi | Villa | Private Pool & A/C
6 bedrooms, 7 beds, 6.5 private bathrooms
2–7 Oct
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5.0 out of 5 average rating, 22 reviews
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
4.99 out of 5 average rating, 85 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
2 bedrooms, 3 beds, 1 bathroom
13–18 Nov
4.97 out of 5 average rating, 116 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
Apartment in Siena
NEW in Siena, Porta Ovile + free private parking
1 bedroom, 1 double bed, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 122 reviews
Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds, 2 bathrooms
8–13 Dec
5.0 out of 5 average rating, 108 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Sept
4.92 out of 5 average rating, 389 reviews
Guest favourite
Villa in Siena
Elf's Hut - Elf's Hut
4 bedrooms, 4 king beds, 4 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 60 reviews
Guest favourite
Flat in San Gusmè
La Dimora del Luca
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
5 bedrooms, 6 beds, 5.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 340 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
5 bedrooms, 6 beds, 4 bathrooms
8–13 Oct
4.99 out of 5 average rating, 151 reviews
Guest favourite
Villa in Sovicille
Farmhouse Podere Il Moro in the nature of Siena
9 bedrooms, 16 beds, 9 bathrooms
15–20 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
1 bedroom, 2 beds, 1 bathroom
11–16 Nov
5.0 out of 5 average rating, 222 reviews
Guest favourite
Apartment in Siena
GuestHost - Stunning Church of San Domenico View
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
4.94 out of 5 average rating, 62 reviews
Guest favourite
Apartment in Siena
Siena Center – Modern Apartment with Parking
2 bedrooms, 3 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 5 reviews