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Search results; Over 1,000 homes in Monteriggioni

Guest favourite
Villa in Monteriggioni
Villa of the 2 Olive Trees (Abbadia Isola)
6 bedrooms, 12 beds, 4 private bathrooms
7–12 Oct, Individual host
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4.97 out of 5 average rating, 174 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
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, 12 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Sept
5.0 out of 5 average rating, 9 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, 84 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 2 - pool and amazing views
Individual host
17–22 Nov
5.0 out of 5 average rating, 65 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
7–12 Sept
4.98 out of 5 average rating, 217 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
Top guest favourite
Farm stay in Sovicille
Agriturismo La Villa - Il Ciliegio, Pool & Garden.
Business host
27 Sept – 2 Oct
4.95 out of 5 average rating, 145 reviews
Top guest favourite
Flat in Poggibonsi
OLIVE TREE APARTMENT - CHIANTI
Individual host
1–6 Apr
4.98 out of 5 average rating, 280 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, 37 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
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews