Gateway to Tuscany
6 guests
2 bedrooms
Gambassi Terme, Florence
Set in the rolling Tuscan hillsides, with the towers of nearby San Gimignano in full view, the setting of this hilltop farmhouse is one-of-a-kind. Inside, the quietly elegant interiors allow the window's vistas to sing, and the mezzanine desk space will be handy for anyone planning to work.
Valley View Villa
4 guests
2 bedrooms
Roccalbegna, Grosseto
This home is part of a development of independently-owned cottages in the countryside that borders the Pescinello natural park. It’s a tranquil place to stay, ideal for those seeking an Italian stay that’s off the beaten track.
I Dream of Chianti
10 guests
5 bedrooms
Gaiole in Chianti, Siena
This former defence watchtower dating back to the 10th century has been beautifully reimagined into a corker of a family home. Within the palatial grounds, there's a ping-pong table, pool table, table-football set, and a children's playground to keep little ones busy and a private secluded pool and sauna for some adult relaxation time.
Hillside Harvest
4 guests
2 bedrooms
Gaiole in Chianti, Siena
Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine.
Explore the 118 most perfect homes in our collection
Discover our curated collection of luxury holiday Cottages in Siena, Tuscany, Italy. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Siena Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.
