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Search results; Over 1,000 homes in Siena

Top guest favourite
Farm stay in Siena
Authentic Tuscan Country House WITH A/C
1 bedroom, 1 bed, 2 private bathrooms
10–15 Oct, Business host
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4.97 out of 5 average rating, 325 reviews
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
24–29 Oct
4.99 out of 5 average rating, 83 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 Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 113 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
Individual host
24–31 Oct
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
2–7 Sept
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
19–24 Oct
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
12–17 Oct
5.0 out of 5 average rating, 40 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
Farm stay in Greve in Chianti
Typical Tuscan country house
Business host
3–8 Dec
4.99 out of 5 average rating, 431 reviews
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
22–27 Sept
4.99 out of 5 average rating, 149 reviews
Top guest favourite
Farm stay in Greve in Chianti
Farmhouse in Chianti with Swimming Pool
Business host
29 Oct – 3 Nov
4.99 out of 5 average rating, 510 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
7–12 Sept
4.98 out of 5 average rating, 216 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
2–7 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Greve in Chianti
Medieval castle (27 beds)-Chianti-Florence 15km
Business host
7–12 Sept
4.99 out of 5 average rating, 73 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, 104 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, 97 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Flat in Siena
Diacceto19 Siena Apartments Int.1
Individual host
20–25 Nov
4.98 out of 5 average rating, 440 reviews