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Search results; Over 1,000 homes in Simignano
Over 1,000 homes in Simignano
Top guest favourite
Guest favourite
Holiday home in loc. Simignano
Casa al Gianni - Oak
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
19–24 Sept
19–24 Sept
,
·
Business host
£1,204
£831
total
Show price breakdown
,
·
4.93 out of 5 average rating, 244 reviews
4.93 (244)
Top guest favourite
Guest favourite
Farm stay in Simignano
Casa al Gianni - Fig
Business host
Business host
21–26 Oct
21–26 Oct
£1,324
£914
total
Show price breakdown
Extended stay discount
Free cancellation
4.92 out of 5 average rating, 288 reviews
4.92 (288)
Top guest favourite
Guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
Business host
24–29 Oct
24–29 Oct
£1,005
total
Show price breakdown
£1,005 total
Free cancellation
4.99 out of 5 average rating, 83 reviews
4.99 (83)
Superhost
Superhost
Holiday home in Sovicille
Exclusive Use TrueTuscanFarm PoolHottubAC Siena20P
Individual host
Individual host
30 Sept – 5 Oct
30 Sept – 5 Oct
£4,724
total
Show price breakdown
£4,724 total
5.0 out of 5 average rating, 6 reviews
5.0 (6)
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
£1,028
£813
total
Show price breakdown
5.0 out of 5 average rating, 40 reviews
5.0 (40)
Top guest favourite
Guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
Business host
9–14 Nov
9–14 Nov
£1,913
£999
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
Farm stay in Monteriggioni
Podere Casalino - Il Gatto
Business host
Business host
7–12 Sept
7–12 Sept
£1,012
total
Show price breakdown
£1,012 total
4.91 out of 5 average rating, 116 reviews
4.91 (116)
Top guest favourite
Guest favourite
Villa in Radicondoli
Leo's Romantic House
Business host
Business host
11–16 Sept
11–16 Sept
£2,261
£1,948
total
Show price breakdown
5.0 out of 5 average rating, 65 reviews
5.0 (65)
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
£2,466
£2,082
total
Show price breakdown
4.98 out of 5 average rating, 217 reviews
4.98 (217)
Top guest favourite
Guest favourite
Farm stay in Radicondoli
The cherry tree, Podere il giglio
Business host
Business host
26 Sept – 1 Oct
26 Sept – 1 Oct
£740
total
Show price breakdown
£740 total
5.0 out of 5 average rating, 33 reviews
5.0 (33)
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
£1,032
total
Show price breakdown
£1,032 total
Free cancellation
4.98 out of 5 average rating, 49 reviews
4.98 (49)
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
Individual host
15–20 Sept
15–20 Sept
£3,003
total
Show price breakdown
£3,003 total
New place to stay
New
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
£1,827
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 141 reviews
5.0 (141)
Top guest favourite
Guest favourite
Villa in Tignano
Villa Isabella
Individual host
Individual host
20–25 Sept
20–25 Sept
£2,403
£1,992
total
Show price breakdown
Free cancellation
4.96 out of 5 average rating, 208 reviews
4.96 (208)
Top guest favourite
Guest favourite
Flat in Ancaiano
Tower house in the countryside with sensory shower
Individual host
Individual host
10–15 Nov
10–15 Nov
£519
total
Show price breakdown
£519 total
Free cancellation
4.98 out of 5 average rating, 118 reviews
4.98 (118)
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
Individual host
18–23 Sept
18–23 Sept
£1,505
£1,354
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
Individual host
11–16 Oct
11–16 Oct
£1,128
£903
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
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
£2,142
total
Show price breakdown
£2,142 total
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Top guest favourite
Guest favourite
Home in Montaione
Cercis - La Palmierina
Individual host
Individual host
24–29 Oct
24–29 Oct
£938
£865
total
Show price breakdown
Free cancellation
4.96 out of 5 average rating, 145 reviews
4.96 (145)
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