The Hilltop Dream
12 guests
6 bedrooms
Radda in Chianti, Tuscany
With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining.
Sage and Rosemary
10 guests
5 bedrooms
Poggibonsi, Siena
Surrounded by 10 hectares of land, featuring olive groves, lush woods and picturesque vineyards, this home is the perfect introduction to the Tuscan countryside. From the terrace, you can take in the view of the region’s rolling hills, with the hilltown of Poggibonsi rising up in the distance.
Chianti Sunrise
4 guests
2 bedrooms
Castelnuovo Berardenga, Siena
Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind.
Wild Roses
10 guests
5 bedrooms
Radda in Chianti, Tuscany
Tucked away in the Tuscan countryside, this idyllic villa promises plenty of rest, relaxation and rustic charm. Famous for its rolling hills, acres of vineyards and quaint, historic hamlets, there's no better spot to explore all this region has to offer.
Explore the 2090 most perfect homes in our collection
You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Castellina in Chianti, Siena, Tuscany, Italy. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Castellina in Chianti Home to Rent with a Swimming Pool today, and set up a holiday to remember.
