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Search results; Over 1,000 homes in Simignano

Top guest favourite
Home in Simignano
Casa al Gianni - The Simignano Barn
5 bedrooms, 5 beds, 4 private bathrooms
31 Oct – 5 Nov, Business host
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4.97 out of 5 average rating, 195 reviews
Top guest favourite
Farm stay in Simignano
Casa al Gianni - Fig
Business host
21–26 Oct
4.92 out of 5 average rating, 288 reviews
Superhost
Holiday home in Sovicille
Exclusive Use TrueTuscanFarm PoolHottubAC Siena20P
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 6 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
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Villa in Radicondoli
Leo's Romantic House
Business host
12–17 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Farm stay in Monteriggioni
Podere Casalino - Il Gatto
Business host
10–15 Sept
4.91 out of 5 average rating, 117 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
13–18 Nov
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
19–24 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Farm stay in Radicondoli
The cherry tree, Podere il giglio
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 33 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 208 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
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
9–14 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Farm stay in Sovicille
Exclusive use of the farmhouse, swimming pool, en-suite rooms, A/C
Business host
3–8 Oct
5.0 out of 5 average rating, 30 reviews
Guest favourite
Cottage in Greve in Chianti
Very cosy cottage with beautiful views
Individual host
4–9 Oct
4.96 out of 5 average rating, 52 reviews