Chianti Hills
12 guests
6 bedrooms
Gaiole in Chianti, Siena
Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool area and an alfresco dining terrace to soak in the vistas, and inside, a second-floor lounge with far-reaching panoramas.
The Sweetest Life
32 guests
16 bedrooms
Monteriggioni, Siena
Staying at this sprawling Tuscan estate is like having your own ancient borgo (small village). Hectares of grounds are dotted with cypress trees, dense woodland, ancient olive groves and gardens blossoming with flowers.
Like Sweetness
8 guests
4 bedrooms
Castellina in Chianti, Tuscany
If you’re looking to experience the natural beauty of Chianti, this home delivers a charming solution. You’ll be welcomed by stunning views across the surrounding vineyards and there’s a private swimming pool for leisurely dips.
The Tuscan Farm
14 guests
7 bedrooms
Sovicille, Tuscany
Whether you’re here for the famous landscapes, rich history, culture or cuisine, one thing’s for sure, if you want to experience Tuscany at its finest, this charming villa is the place to be. In an idyllic countryside location, this home is surrounded by luscious greenery, rolling hills and landscapes, making it the ideal spot for sunset views and stargazing.
Explore the 2344 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 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 Siena Home to Rent with a Swimming Pool today, and set up a holiday to remember.
