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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
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
Farm stay in Sovicille
Agriturismo La Villa - Il Ciliegio, Pool & Garden.
Business host
27 Sept – 2 Oct
4.95 out of 5 average rating, 146 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
Guest favourite
Villa in Radicondoli
Private Tuscan villa with pool steps from village
Business host
18–23 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Siena
Secret Garden Siena
Individual host
2–7 Nov
4.98 out of 5 average rating, 220 reviews
Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
8–13 Dec
5.0 out of 5 average rating, 108 reviews
Top guest favourite
Home in Montaione
Cercis - La Palmierina
Individual host
27 Oct – 1 Nov
4.96 out of 5 average rating, 146 reviews
Top guest favourite
Farm stay in Simignano
Casa al Gianni - Hut
Business host
12–17 Nov
4.93 out of 5 average rating, 292 reviews
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
Individual host
30 Oct – 4 Nov
4.99 out of 5 average rating, 472 reviews
Top guest favourite
Farm stay in Montecerboli
Gelsomino Apartment in Agriturismo with Pool
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 27 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
Top guest favourite
Flat in Radicondoli
SerenaHouse
Individual host
1–6 Oct
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
16–21 Sept
4.92 out of 5 average rating, 389 reviews
Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
Business host
19–24 Oct
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Farm stay in Monteroni d'Arbia
The Arches of Corsanello | Apt "Siena" x 3
Business host
30 Oct – 4 Nov
4.97 out of 5 average rating, 77 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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