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Search results; Over 1,000 homes in Asciano

Farm stay in Asciano
The Lazy Olive 5 apartments - Vite
1 bedroom, 1 bed, 1 private bathroom
30 Sept – 5 Oct, Business host
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Superhost
Flat in San Giovanni d'Asso
Podere Ferranino #Alberti Townhouse
Business host
12–19 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Asciano
In_Bangaia
Individual host
2–7 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
Individual host
18–23 Nov
4.98 out of 5 average rating, 116 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, 84 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, 76 reviews
Top guest favourite
Home in Montisi
Private 16th century farmhouse
Business host
17–24 Apr
5.0 out of 5 average rating, 22 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
7–12 Sept
5.0 out of 5 average rating, 3 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 Lucignano
Palazzo Trapani Luxury Residence
2 bedrooms, 1 bed, 2.5 bathrooms
13–18 Nov
4.9 out of 5 average rating, 42 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
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 113 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, 57 reviews
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 Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
Individual host
29 Sept – 4 Oct
5.0 out of 5 average rating, 21 reviews
Villa in Rapolano Terme
Castellare 14, Emma Villas
Business host
20–25 Sept
Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
12–17 Oct
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Montalcino
Villa Cipressino
Individual host
3–8 Sept
5.0 out of 5 average rating, 12 reviews