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Search results; Over 1,000 homes

Top guest favourite
Cottage in Ponte Feccia
Country cottage C&M surrounded by greenery, love Tuscany
1 bedroom, 3 beds, 1 private bathroom
20–25 Oct, Individual host
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4.95 out of 5 average rating, 200 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 Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
24–29 Oct
4.99 out of 5 average rating, 83 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
9–14 Nov
4.97 out of 5 average rating, 115 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, 288 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, 217 reviews
Top 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, 112 reviews
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
8–13 Sept
4.99 out of 5 average rating, 137 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, 84 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, 49 reviews
Top guest favourite
Farm stay in Monteriggioni
Podere Casalino - Il Gatto
Business host
7–12 Sept
4.91 out of 5 average rating, 116 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
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
Guest favourite
Villa in Radicondoli
Mulino di Anqua: A Tuscan Oasis
Individual host
4–9 Sept
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Montaione
Cercis - La Palmierina
Individual host
24–29 Oct
4.96 out of 5 average rating, 145 reviews
Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
Individual host
8–13 Oct
4.98 out of 5 average rating, 64 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
3–8 Sept
5.0 out of 5 average rating, 4 reviews