Search results; Over 1,000 homes

Top guest favourite
Room in Monterongriffoli
Morning Glory -Truffle N Bed
15-min walk
3–8 Aug
4.95 out of 5 average rating, 60 reviews
Top guest favourite
Home in Montalcino
Villa Cipressino
10-min drive
21–26 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Pienza
Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
30-min drive
22–27 Aug
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Apartment in Pienza
Mascagni Farmhouse in Val d'Orcia, Pienza
30-min drive
19–24 Oct
5.0 out of 5 average rating, 154 reviews
Superhost
Flat in Montalcino
Wp Relais Argante Apartment
30-min drive
23–28 Jul
Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
30-min drive
20–25 Jul
4.98 out of 5 average rating, 115 reviews
Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
50-min drive
15–20 Jul
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 beds
20–25 Nov
5.0 out of 5 average rating, 95 reviews
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
3 beds
25–30 Jul
Home in Castelnuovo dell'Abate
Modern Home near Montalcino with Private Garden
40-min drive
25–30 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Tiny home in Pienza
Selvoli Farmhouse – The School
40-min drive
3–8 Oct
4.93 out of 5 average rating, 68 reviews
Top guest favourite
Home in Monteroni d'Arbia
Villa Canina - charm and rurality in the Crete Senesi
60-min drive
20–25 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
5 beds
19–24 Oct
5.0 out of 5 average rating, 47 reviews
Villa in Lucignano
[Between Cortona and Siena] 1000 sqm Villa | Pool & Tennis
40-min drive
25–30 Jul
New place to stay
Top guest favourite
Farm stay in Seggiano
Terra Delle Sidhe, Seggiano, Tuscany, Italy
60-min drive
31 Aug – 5 Sept
4.99 out of 5 average rating, 283 reviews
Top guest favourite
Cottage in Buonconvento
Hut at S. Carlo in Buonconvento
30-min drive
1–8 Sept
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Apartment in Montefollonico
Toskana Charme: Montefollonico!
40-min drive
14–19 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Montalcino
City Center Palazzo: 4 King BR 6 Bath and Garage
30-min drive
1–6 Aug
5.0 out of 5 average rating, 23 reviews