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Search results; Over 1,000 homes
Over 1,000 homes
Guest favourite
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
1–6 Oct
,
·
Individual host
£487
total
Show price breakdown
£487 total
,
·
4.94 out of 5 average rating, 203 reviews
4.94 (203)
Top guest favourite
Guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
Individual host
21–26 Oct
21–26 Oct
£1,031
£947
total
Show price breakdown
5.0 out of 5 average rating, 40 reviews
5.0 (40)
Guest favourite
Guest favourite
Home in Pievescola
Borgo Ripostena – no. 8 Casa Vecchia
Business host
Business host
18–23 Oct
18–23 Oct
£811
total
Show price breakdown
£811 total
Free cancellation
4.95 out of 5 average rating, 201 reviews
4.95 (201)
Top guest favourite
Guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
Business host
10–15 Oct
10–15 Oct
£1,030
total
Show price breakdown
£1,030 total
Free cancellation
4.99 out of 5 average rating, 85 reviews
4.99 (85)
Top guest favourite
Guest favourite
Holiday home in Monteroni d'Arbia
Tuja
Business host
Business host
22–27 Oct
22–27 Oct
£1,423
total
Show price breakdown
£1,423 total
Free cancellation
5.0 out of 5 average rating, 35 reviews
5.0 (35)
Top guest favourite
Guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
Business host
20–25 Oct
20–25 Oct
£2,093
£1,822
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 141 reviews
5.0 (141)
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
Individual host
15–20 Sept
15–20 Sept
£2,995
total
Show price breakdown
£2,995 total
New place to stay
New
Top guest favourite
Guest favourite
Farm stay in Simignano
Casa al Gianni - Hut
Business host
Business host
12–17 Nov
12–17 Nov
£861
£620
total
Show price breakdown
Extended stay discount
Free cancellation
4.93 out of 5 average rating, 291 reviews
4.93 (291)
Guest favourite
Guest favourite
Holiday home in Monteroni d'Arbia
White lily with a view of Siena
Individual host
Individual host
21–26 Sept
21–26 Sept
£871
total
Show price breakdown
£871 total
4.92 out of 5 average rating, 113 reviews
4.92 (113)
Top guest favourite
Guest favourite
Apartment in Siena
Luxury penthouse with a view of Piazza del Campo
Individual host
Individual host
25–30 Oct
25–30 Oct
£3,238
total
Show price breakdown
£3,238 total
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Top guest favourite
Guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
Business host
13–18 Nov
13–18 Nov
£2,139
£1,117
total
Show price breakdown
Extended stay discount
Free cancellation
4.97 out of 5 average rating, 116 reviews
4.97 (116)
Top guest favourite
Guest favourite
Home in Chiusdino
La Capanna: country house with magnificent view
Individual host
Individual host
3–8 Oct
3–8 Oct
£659
total
Show price breakdown
£659 total
4.92 out of 5 average rating, 85 reviews
4.92 (85)
Top guest favourite
Guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
Individual host
6–11 Oct
6–11 Oct
£2,291
total
Show price breakdown
£2,291 total
Free cancellation
4.98 out of 5 average rating, 218 reviews
4.98 (218)
Guest favourite
Guest favourite
Villa in Roccatederighi
Villa Casale "Il Diaccio" with views of the Maremma
Individual host
Individual host
2–7 Nov
2–7 Nov
£1,613
total
Show price breakdown
£1,613 total
Free cancellation
4.94 out of 5 average rating, 18 reviews
4.94 (18)
Top guest favourite
Guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
Individual host
28 Oct – 2 Nov
28 Oct – 2 Nov
£1,406
£1,226
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
Business host
27 Oct – 1 Nov
27 Oct – 1 Nov
£1,029
total
Show price breakdown
£1,029 total
Free cancellation
4.98 out of 5 average rating, 51 reviews
4.98 (51)
Top guest favourite
Guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
Individual host
Individual host
18–23 Oct
18–23 Oct
£569
total
Show price breakdown
£569 total
Free cancellation
4.98 out of 5 average rating, 65 reviews
4.98 (65)
Top guest favourite
Guest favourite
Farm stay in Monteriggioni
Podere Casalino - Il Gatto
Business host
Business host
15–20 Sept
15–20 Sept
£1,009
total
Show price breakdown
£1,009 total
4.91 out of 5 average rating, 117 reviews
4.91 (117)
Top guest favourite
Guest favourite
Villa in Tignano
Villa Isabella
Individual host
Individual host
20–25 Sept
20–25 Sept
£1,971
total
Show price breakdown
£1,971 total
4.96 out of 5 average rating, 209 reviews
4.96 (209)
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