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Search results; Over 1,000 homes in Monsanto I

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Guest favourite
Villa in Monsanto
La Cipresseta Estate | Cipresso House
2 bedrooms, 3 beds, 1 private bathroom
10–15 Oct, Individual host
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4.98 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
15–20 Oct
5.0 out of 5 average rating, 6 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
New place to stay
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Guest favourite
Flat in Poggibonsi
Capanna, typical house in Chianti with pool
Individual host
21–26 Sept
4.97 out of 5 average rating, 59 reviews
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Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
27 Oct – 1 Nov
4.95 out of 5 average rating, 57 reviews
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Flat in Poggibonsi
Borgo Apt. with ac near Siena
Business host
21–26 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
Individual host
18–23 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
19–24 Sept
4.98 out of 5 average rating, 61 reviews
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Room in Barberino Tavarnelle
Margherita Room - Le Querciole di Mauro Corsi
Individual host
19–24 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Farm stay in Montaione
Tenuta Collerucci | Villa with private pool
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 57 reviews
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Top guest favourite
Farm stay in San Gimignano
Casa Renai - holidays with friends in San Gimignano
Business host
18–23 Oct
5.0 out of 5 average rating, 49 reviews
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Rooms in Barberino Val d'Elsa
Four-Poster Bed | Agriturismo with Pool | Chianti
Business host
30 Sept – 5 Oct
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Flat in Poggibonsi
small apartment 90 metres from Siena Eye Laser
Individual host
3–8 Oct
New place to stay
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Top guest favourite
Apartment in San Gimignano
Casaglia Residence
Individual host
5–10 Oct
4.97 out of 5 average rating, 75 reviews
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Room in Barberino Val d'Elsa
Compact Double | Chianti | Pool & Restaurant
Business host
4–9 Oct