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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
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
Top guest favourite
Holiday home in Monteroni d'Arbia
Tuja
Business host
22–27 Oct
5.0 out of 5 average rating, 35 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
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
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
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
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 reviews
Guest favourite
Villa in Roccatederighi
Villa Casale "Il Diaccio" with views of the Maremma
Individual host
2–7 Nov
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 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
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 Monteriggioni
Podere Casalino - Il Gatto
Business host
15–20 Sept
4.91 out of 5 average rating, 117 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 209 reviews