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Search results; Over 1,000 homes in Monti

Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 1 bed, 5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Room in Gaiole in Chianti
Argentina. Welcome to our small village, L...
2 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 48 reviews
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 472 reviews
Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
7 bedrooms, 8 beds, 7 bathrooms
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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, 141 reviews
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
5 bedrooms, 7 beds, 4 bathrooms
19–24 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 4 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in San Gusmè
La Dimora del Luca
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
4 bedrooms, 6 beds, 4 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds, 7 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 115 reviews
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
4 bedrooms, 6 beds, 4 bathrooms
15–20 Sept
New place to stay