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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
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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
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
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 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
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
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 Montecatini Val di Cecina
Belforti Tower
Business host
8–13 Sept
4.99 out of 5 average rating, 137 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 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
Home in Montaione
Cercis - La Palmierina
Individual host
24–29 Oct
4.96 out of 5 average rating, 145 reviews
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Sept
5.0 out of 5 average rating, 9 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
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