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Search results; Over 1,000 homes

Guest favourite
Cottage in Ponte Feccia
Country cottage C&M surrounded by greenery, love Tuscany
1 bedroom, 3 beds, 1 private bathroom
1–6 Oct, Individual host
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4.94 out of 5 average rating, 203 reviews
Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
21–26 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Pievescola
Borgo Ripostena – no. 8 Casa Vecchia
Business host
18–23 Oct
4.95 out of 5 average rating, 201 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
10–15 Oct
4.99 out of 5 average rating, 85 reviews
Guest favourite
Holiday home in Monteroni d'Arbia
White lily with a view of Siena
Individual host
21–26 Sept
4.92 out of 5 average rating, 113 reviews
Top guest favourite
Home in Chiusdino
La Capanna: country house with magnificent view
Individual host
3–8 Oct
4.92 out of 5 average rating, 85 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 Asciano
Incredible Views & Pool in the Tuscan Hills
Business host
21–26 Oct
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
13–18 Nov
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Farm stay in Simignano
Casa al Gianni - Hut
Business host
12–17 Nov
4.93 out of 5 average rating, 291 reviews
Guest favourite
Villa in Monterotondo Marittimo
Il Poderino Guest House
Business host
26 Sept – 3 Oct
5.0 out of 5 average rating, 7 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
Flat in Roccatederighi
Domus Olea BnB
Individual host
5–10 Oct
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
Individual host
18–23 Oct
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 reviews
Guest favourite
Villa in Monteroni d'Arbia
Panoramic villa in Crete Senesi, overlooking Siena.
Business host
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 208 reviews
Guest favourite
Villa in Siena
Elf's Hut - Elf's Hut
Business host
26 Sept – 1 Oct
4.97 out of 5 average rating, 60 reviews