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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, 289 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, 84 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Villa in Radicondoli
Leo's Romantic House
Business host
11–16 Sept
5.0 out of 5 average rating, 65 reviews
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
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
9–14 Nov
4.97 out of 5 average rating, 116 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
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 Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
27 Oct – 1 Nov
4.98 out of 5 average rating, 49 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
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
Business host
1–6 May
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 208 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
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
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
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
22–27 Sept
4.99 out of 5 average rating, 149 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