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Search results; Over 1,000 homes in Simignano

Top guest favourite
Holiday home in loc. Simignano
Casa al Gianni - Oak
2 bedrooms, 3 beds, 1 private bathroom
19–24 Sept, Business host
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4.93 out of 5 average rating, 244 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
24–29 Oct
4.99 out of 5 average rating, 83 reviews
Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
12–17 Oct
5.0 out of 5 average rating, 40 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
Villa in Radicondoli
Leo's Romantic House
Business host
11–16 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
7–12 Sept
4.98 out of 5 average rating, 217 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 Radicondoli
The cherry tree, Podere il giglio
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 33 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, 49 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
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
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 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
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Sept
5.0 out of 5 average rating, 9 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
18–23 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews