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Search results; Over 1,000 homes in Monteriggioni

Top guest favourite
Cottage in Monteriggioni
Monteriggioni Castello, holiday house in Tuscany
2 bedrooms, 7 beds, 1 private bathroom
1–6 Nov, Business host
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4.95 out of 5 average rating, 296 reviews
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
Guest favourite
Room in Monteriggioni
Rooms and Wine Monteriggioni, Il chianti
Business host
3–8 Nov
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Home in Monteriggioni
Under the Walls of Monteriggioni
Individual host
14–19 Sept
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 388 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
10–15 Oct
4.99 out of 5 average rating, 85 reviews
Top guest favourite
Home in Siena
La Casina del Castagno
Individual host
5–10 Oct
4.97 out of 5 average rating, 39 reviews
Guest favourite
Townhouse in Colle di Val d'Elsa
L'Arco
Business host
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Farm stay in Simignano
Casa al Gianni - Fig
Business host
21–26 Oct
4.92 out of 5 average rating, 288 reviews
Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
Business host
20–25 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Home in Colle di Val d'Elsa
Casa Emilio
Business host
23–28 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Ancaiano
Tower house in the countryside with sensory shower
Individual host
10–15 Nov
4.98 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 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