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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
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, 15 reviews
Home in Monteriggioni
Under the Walls of Monteriggioni
Individual host
18–23 Sept
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
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, 119 reviews
Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 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
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
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Farm stay in Sovicille
Agriturismo La Villa - Il Ciliegio, Pool & Garden.
Business host
29 Sept – 4 Oct
4.95 out of 5 average rating, 146 reviews
Top guest favourite
Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
Business host
11–16 Nov
5.0 out of 5 average rating, 222 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews