Tuscan Cottage
2 guests
1 bedrooms
Radda in Chianti, Tuscany
This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence.
Beneath the Sun
2 guests
1 bedrooms
Barberino Tavarnelle, Florence
This former barn has been transformed into a rustic sanctuary where you can slow down and savour the magic of Italian living. Nestled in the grounds of the owner’s private home, the house offers peace, privacy and all the essentials you could need for a romantic break or solo retreat.
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.
Tuscan Flow
4 guests
2 bedrooms
Castelnuovo Berardenga, Siena
Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court.
Explore the 92 most perfect homes in our collection
Discover our curated collection of luxury holiday Cottages in Castiglion Fiorentino, Arezzo, 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 Castiglion Fiorentino 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.
