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Search results; Over 1,000 homes in Asciano

Guest favourite
Home in Asciano
Charming House Rental with infinity pool
2 bedrooms, 3 beds, 2 private bathrooms
16–22 Sept, Individual host
,
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Asciano
In_Bangaia
Individual host
16–21 Sept
5.0 out of 5 average rating, 23 reviews
Superhost
Flat in San Giovanni d'Asso
Podere Ferranino #Alberti Townhouse
Business host
19–26 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, 11 reviews
Top guest favourite
Home in Cortona
Relais Tosca Slow and Rural Life
Individual host
26 Sept – 1 Oct
5.0 out of 5 average rating, 6 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
Flat in Rigomagno
Podere la Casina Country Chic apt. Myrtus
Business host
28 Sept – 3 Oct
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 Sinalunga
Villa Panorama near Siena Tuscany
Business host
14–20 Sept
5.0 out of 5 average rating, 54 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
13–18 Sept
5.0 out of 5 average rating, 4 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
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
13–18 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
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
Home in Montisi
Private 16th century farmhouse
Business host
17–24 Apr
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
Business host
11–16 Nov
5.0 out of 5 average rating, 222 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