filters

Search results; Over 1,000 homes in Monsanto II

Photo 1 of 23
Top guest favourite
Home in Monsanto II
The cottage in Chianti with a small breakfast
2 bedrooms, 4 beds, 1 private bathroom
11–16 Oct
,
4.96 out of 5 average rating, 52 reviews
Photo 1 of 29
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 61 reviews
Photo 1 of 29
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 143 reviews
Photo 1 of 29
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
15–20 Oct
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
1–6 Oct
Photo 1 of 29
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 38 reviews
Photo 1 of 29
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 57 reviews
Photo 1 of 29
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 69 reviews
Photo 1 of 29
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds, 3.5 bathrooms
27 Oct – 1 Nov
4.99 out of 5 average rating, 115 reviews
Photo 1 of 29
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 30 reviews
Photo 1 of 29
Guest favourite
Flat in Poggibonsi
Capanna, typical house in Chianti with pool
1 bedroom, 1 double bed, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 59 reviews
Photo 1 of 29
Luxe
Villa in Barberino Tavarnelle
Villa Chianti Fornace
6 bedrooms, 6 beds, 5 bathrooms
17–24 Oct
4.86 out of 5 average rating, 14 reviews
Photo 1 of 24
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Superhost
Flat in Poggibonsi
Sole: Rustic Escape Tuscany private park @ Chianti
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
3 bedrooms, 3 beds, 3.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 19 reviews
Photo 1 of 29
Top guest favourite
Farm stay in Greve in Chianti
Ancient Tuscan farmhouse in the Chianti hills
2 bedrooms, 2 double beds, 1 bathroom
23–28 Nov
4.99 out of 5 average rating, 285 reviews
Photo 1 of 29
Top guest favourite
Villa in Siena
Exclusive Villa Mami
6 bedrooms, 6 beds, 6.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 25 reviews
Photo 1 of 6
Rooms in Barberino Val d'Elsa
Four-Poster Bed | Agriturismo with Pool | Chianti
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct