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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
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
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
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
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
Business host
1–6 May
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
9–14 Sept
5.0 out of 5 average rating, 10 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
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
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 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
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
19–24 Oct
4.98 out of 5 average rating, 218 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
Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 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
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
10–15 Oct
4.98 out of 5 average rating, 47 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
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