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Search results; Over 1,000 homes in Simignano

Top guest favourite
Farm stay in Simignano
Casa al Gianni - Hut
1 bedroom, 1 bed, 1 private bathroom
12–17 Nov, Business host
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4.93 out of 5 average rating, 292 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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Superhost
Villa in Sovicille
Agriturismo La Villa - Chesnut & Olive Tree House
Business host
2–8 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Radicondoli
Leo's Romantic House
Business host
21–26 Sept
5.0 out of 5 average rating, 66 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, 55 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 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
Guest favourite
Farm stay in Sovicille
Tuscan Villa: Pool, Hot Tub, 4bd, A/C, Wi-Fi, Siena
Business host
21–26 Oct
5.0 out of 5 average rating, 5 reviews
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, 51 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 209 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
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
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
18–23 Sept
4.98 out of 5 average rating, 60 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
Apartment in Siena
Luxury penthouse with a view of Piazza del Campo
Individual host
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Villa in Montecastelli Pisano
Exclusive villa with pool jacuzzi wifi and green
Business host
20–27 Mar
4.96 out of 5 average rating, 53 reviews