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Search results; Over 1,000 homes in Siena
Over 1,000 homes in Siena
Guest favourite
Guest favourite
Boutique hotel in Siena
Sleeping on Siena roof
1 bedroom
,
·
1 bed
,
·
1 private bathroom
18–23 Oct
18–23 Oct
,
·
Business host
£715
total
Show price breakdown
£715 total
,
·
4.96 out of 5 average rating, 192 reviews
4.96 (192)
Top guest favourite
Guest favourite
Villa in Impruneta
Private Estate - Personal Concierge & heated pool
Individual host
Individual host
4–9 Oct
4–9 Oct
£8,376
£6,862
total
Show price breakdown
Free cancellation
4.99 out of 5 average rating, 145 reviews
4.99 (145)
Top guest favourite
Guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
Individual host
6–11 Sept
6–11 Sept
£3,128
total
Show price breakdown
£3,128 total
4.99 out of 5 average rating, 113 reviews
4.99 (113)
Top guest favourite
Guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
Business host
7–12 Oct
7–12 Oct
£2,394
total
Show price breakdown
£2,394 total
Free cancellation
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Top guest favourite
Guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
Business host
29 Nov – 4 Dec
29 Nov – 4 Dec
£821
£740
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 53 reviews
5.0 (53)
Top guest favourite
Guest favourite
Villa in Gaiole in Chianti
Sestuccia
Individual host
Individual host
24–31 Oct
24–31 Oct
£4,295
£3,783
total
Show price breakdown
Free cancellation
4.99 out of 5 average rating, 74 reviews
4.99 (74)
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
Individual host
3–8 Sept
3–8 Sept
£1,536
£1,382
total
Show price breakdown
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
Individual host
7–12 Sept
7–12 Sept
£2,461
£2,077
total
Show price breakdown
4.98 out of 5 average rating, 217 reviews
4.98 (217)
Top guest favourite
Guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
23–28 Oct
23–28 Oct
£1,377
total
Show price breakdown
£1,377 total
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Top guest favourite
Guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
Individual host
30 Nov – 5 Dec
30 Nov – 5 Dec
£523
£453
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 104 reviews
5.0 (104)
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
£3,240
total
Show price breakdown
£3,240 total
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
Individual host
15–20 Sept
15–20 Sept
£2,997
total
Show price breakdown
£2,997 total
New place to stay
New
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
£1,030
total
Show price breakdown
£1,030 total
Free cancellation
4.98 out of 5 average rating, 49 reviews
4.98 (49)
Top guest favourite
Guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
Business host
22–27 Sept
22–27 Sept
£5,044
total
Show price breakdown
£5,044 total
Free cancellation
4.99 out of 5 average rating, 149 reviews
4.99 (149)
Top guest favourite
Guest favourite
Farm stay in Greve in Chianti
Farmhouse with pool in Chianti
Business host
Business host
17–22 Nov
17–22 Nov
£609
total
Show price breakdown
£609 total
Free cancellation
4.98 out of 5 average rating, 444 reviews
4.98 (444)
Top guest favourite
Guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
Individual host
12–17 Oct
12–17 Oct
£1,026
£812
total
Show price breakdown
5.0 out of 5 average rating, 40 reviews
5.0 (40)
Top guest favourite
Guest favourite
Farm stay in Siena
Typical Tuscan Country House WITH A/C
Business host
Business host
12–17 Oct
12–17 Oct
£1,002
total
Show price breakdown
£1,002 total
Free cancellation
4.98 out of 5 average rating, 290 reviews
4.98 (290)
Top guest favourite
Guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
Individual host
Individual host
2–7 Nov
2–7 Nov
£1,359
total
Show price breakdown
£1,359 total
Free cancellation
5.0 out of 5 average rating, 97 reviews
5.0 (97)
Top guest favourite
Guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
Business host
6–11 Sept
6–11 Sept
£2,146
total
Show price breakdown
£2,146 total
5.0 out of 5 average rating, 9 reviews
5.0 (9)
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