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Search results; Over 1,000 homes in Montebenichi

Guest favourite
Flat in Montebenichi
Agriturismo I Moraioli apartment Parata
1 bedroom, 1 bed, 1 private bathroom
30 Oct – 4 Nov, Business host
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5.0 out of 5 average rating, 19 reviews
Guest favourite
Holiday home in Montebenichi
Agriturismo I Moraioli, Cantina apartment
Business host
13–18 Nov
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Montebenichi
[Little Escape] 4 Beds + Private Panoramic Pool
Individual host
1–6 Oct
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 77 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
19–24 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
Individual host
30 Oct – 4 Nov
4.99 out of 5 average rating, 471 reviews
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
12–17 Sept
4.98 out of 5 average rating, 59 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
10–15 Sept
4.99 out of 5 average rating, 114 reviews
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
22–27 Sept
4.99 out of 5 average rating, 149 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–14 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Villa in Monte San Savino
Villa Tonacato - Charming Villa with private pool
Individual host
6–11 Oct
4.99 out of 5 average rating, 107 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
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
Business host
1–6 Nov
4.84 out of 5 average rating, 109 reviews
Top guest favourite
Apartment in Noce
Podere Vergianoni nestled in Chianti with a pool
Business host
11–16 Nov
5.0 out of 5 average rating, 350 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccina
Individual host
31 Oct – 7 Nov
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Farm stay in Reggello
Il Palazzaccio
Individual host
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
19–26 Sept
5.0 out of 5 average rating, 10 reviews