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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
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
18–23 Sept
4.98 out of 5 average rating, 60 reviews
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Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
18–23 Sept
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Flat in Poggibonsi
Borgo Apt. with ac near Siena
Business host
20–25 Sept
5.0 out of 5 average rating, 4 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
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 56 reviews
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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
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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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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 reviews
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Guest favourite
Flat in Poggibonsi
Cozy tourist house for 4 guests, top relaxation!
Individual host
16–21 Oct
5.0 out of 5 average rating, 9 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, 14 reviews
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Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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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
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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