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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
7–12 Nov, Business host
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5.0 out of 5 average rating, 20 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, 75 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, 78 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
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 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
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
14–19 Sept
4.98 out of 5 average rating, 59 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, 108 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
Flat in San Gusmè
La Dimora del Luca
Individual host
8–13 Nov
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
8–13 Dec
5.0 out of 5 average rating, 108 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, 151 reviews
Top guest favourite
Villa in Pergine Valdarno
La Vignaccia (Farmhouse) - villa w/private pool
Business host
26 Sept – 3 Oct
4.96 out of 5 average rating, 101 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
Sestuccina
Individual host
31 Oct – 7 Nov
4.93 out of 5 average rating, 46 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
Guest favourite
Home in Rapolano Terme
The Golden Stone
Individual host
11–16 Oct
4.92 out of 5 average rating, 12 reviews