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Search results; Over 1,000 homes in Chianni

Top guest favourite
Cottage in Chianni
Cozy Italian stone cottage central Tuscany
3 bedrooms, 4 beds, 2 private bathrooms
21–26 Sept
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4.94 out of 5 average rating, 71 reviews
Top guest favourite
Home in Morrona
Villino Isotta (exclusive private villa)
Individual host
15–20 Oct
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in San Casciano In Val di Pesa
Authentic Tuscan home: history, wine and relax
Individual host
20–25 Sept
5.0 out of 5 average rating, 44 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Barberino Tavarnelle
Relaxing Tuscan Country Home with Beautiful Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Flat in San Miniato
San Miniato - Panoramic terrace in the historic center
Individual host
1–6 Nov
4.99 out of 5 average rating, 173 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
3–8 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Flat in Impruneta
Relaxing Tuscan Terrazza near Florence 4|Shared Po
Business host
31 Oct – 5 Nov
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in San Miniato
Tuscan Palazzo with Original Frescoes & Views
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Volterra
Marta's Domus
Individual host
3–8 Oct
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
Individual host
8–13 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Vinci
Il Palagio
Individual host
18–23 Oct
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Monteroni d'Arbia
Villa Canina - charm and rurality in the Crete Senesi
Individual host
23–28 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Pisa
Greenhouse Seal
Business host
10–15 Oct
5.0 out of 5 average rating, 9 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
3–8 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Volterra
Olive Harmony Tuscan Escape with Pool
Business host
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Ponteginori
Tenuta Tegolaia
Individual host
23–28 Sept
5.0 out of 5 average rating, 29 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Flat in Rivalto
La Piazzetta
Individual host
4–9 Sept