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Search results; Over 1,000 homes in Monteriggioni

Top guest favourite
Farm stay in Monteriggioni
Podere Casalino - Il Gatto
2 bedrooms, 3 beds, 2 private bathrooms
9–14 Sept, Business host
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4.91 out of 5 average rating, 117 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, La prima
Business host
31 Oct – 5 Nov
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
8–13 Sept
5.0 out of 5 average rating, 10 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
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Siena
Relay moderno a Siena
Individual host
18–23 Oct
4.98 out of 5 average rating, 124 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, 84 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
18–23 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Siena
the chestnut house
Individual host
5–10 Oct
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
Business host
9–14 Nov
4.97 out of 5 average rating, 116 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, 85 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
Guest favourite
Cottage in Greve in Chianti
Very cosy cottage with beautiful views
Individual host
4–9 Oct
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Barn in Monteriggioni
Charming Barn with Pool - Chianti Area
Individual host
20–25 Sept
4.98 out of 5 average rating, 64 reviews
Guest favourite
Farm stay in Siena
"Annarosa" Apartment on Chianti hills
Business host
8–13 Mar
4.87 out of 5 average rating, 55 reviews
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
Top guest favourite
Apartment in Noce
Historic 17th-century farm in Chianti, Tuscany
Business host
11–16 Nov
5.0 out of 5 average rating, 220 reviews