Vino on the Terrace
4 guests
2 bedrooms
Gaiole in Chianti, Siena
Part of a 13th-century estate-turned-resort, this apartment makes the most of its scenic location in Chianti. Alongside a private terrace, you'll have access to a communal hilltop swimming pool, shared laundry room, and walking trails through the nearby vineyards.
The Vines of the Vineyard
2 guests
2 bedrooms
Gaiole in Chianti, Siena
Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold.
The Daisy Cutter
10 guests
5 bedrooms
Bucine, Arezzo
This rustic villa caught our eye for its remote location and peaceful countryside surroundings (best enjoyed off the secret terrace accessed from the fifth bedroom). The nearest town of Ambra lies 10km away, so car hire is essential – though there'll be no interruptions here.
Tuscany Magic
8 guests
4 bedrooms
Castelnuovo Berardenga, Siena
Step into a piece of history here – once the dwelling of wandering priests a millennium ago, now transformed into holiday homes. Each villa boasts its own terrace, inviting you to savour alfresco meals and unwind with a glass of Chianti overlooking the Tuscan hills.
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