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Search results; Over 1,000 homes in Asciano

Superhost
Home in Asciano
Family Forest - Pool in the Crete Senesi
2 bedrooms, 4 beds, 2 private bathrooms
11–16 Nov
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4.91 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Asciano
In_Bangaia
1 bedroom, 1 double bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Monteroni d'Arbia
Villa Canina - charm and rurality in the Crete Senesi
2 bedrooms, 3 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 10 reviews
Superhost
Flat in San Giovanni d'Asso
Podere Ferranino #Alberti Townhouse
3 bedrooms, 5 beds, 2 bathrooms
12–19 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
3 bedrooms, 4 beds, 3 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 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, 55 reviews
Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
5 bedrooms, 5 double beds, 5.5 bathrooms
18–23 Nov
4.98 out of 5 average rating, 116 reviews
Superhost
Flat in Asciano
Charme and Beauty - Tuscan Views
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
3 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 23 reviews
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
Serviced apartment in Rigomagno
Podere la Casina Country Chic apt. Myrtus
2 bedrooms, 2 double beds, 1 bathroom
19–24 Sept
Top guest favourite
Home in Asciano
"Le Arcate" apartment in an 18th-century farmhouse
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Monteroni d'Arbia
Discover Tuscany • Peaceful Country Retreat
2 bedrooms, 2 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
2 bedrooms, 6 beds, 3 bathrooms
22–27 Sept
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Cottage in Osteria delle Noci
Your Tuscan oak tree house, enchanting Val d'Orcia
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 115 reviews
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Montalcino
Villa Cipressino
4 bedrooms, 5 beds, 5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Farm stay in Sinalunga
Villa Panorama near Siena Tuscany
4 bedrooms, 6 beds, 4 bathrooms
13–19 Sept
5.0 out of 5 average rating, 53 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay