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Search results; Over 1,000 homes in Asciano

Top guest favourite
Flat in Asciano
Siena - apartment in the countryside near Siena
3 bedrooms, 4 beds, 2 private bathrooms
10–15 Oct, Business host
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4.95 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Asciano
In_Bangaia
Individual host
11–16 Oct
5.0 out of 5 average rating, 21 reviews
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 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
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
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
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
9–14 Sept
4.99 out of 5 average rating, 114 reviews
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, 23 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
8–13 Sept
5.0 out of 5 average rating, 4 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Flat in Lucignano
Palazzo Trapani Luxury Residence
2 bedrooms, 1 bed, 2.5 bathrooms
13–18 Nov
4.91 out of 5 average rating, 44 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
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
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
Flat in Rigomagno
Podere la Casina Country Chic apt. Myrtus
Business host
19–24 Sept
Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
Individual host
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 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
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
Individual host
21–26 Oct
5.0 out of 5 average rating, 40 reviews