One of the Greats
10 guests
5 bedrooms
San Gimignano, Siena
Nestled away in the countryside outside the idyllic hilltown of San Gimignano, this extraordinary villa combines exquisite interior design and a sprawling collection of amenities to make for an address that is sure to win over even the most discerning of guests. As you walk about the house for the first time, you might find it difficult to single out a favourite room.
Tuscan Roses
10 guests
5 bedrooms
Castelnuovo Berardenga, Siena
Located amidst the rolling hills and vineyards of Chianti, this Tuscan oasis makes for a serene retreat. There is plenty of space inside for the whole brood to spread out, thanks to an array of lounges and cosy bedrooms.
Olive Green
4 guests
2 bedrooms
Bucine, Arezzo
You could never tire of the rolling hill vistas seen from the private terrace of this pet-friendly Chianti apartment. Set in a handsome farmhouse dating to the 15th century, the home has been reimagined into five independent apartments with a shared swimming pool surrounded by hectares of olive groves at its heart.
The Chianti Hills
8 guests
4 bedrooms
Gaiole in Chianti, Siena
This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comfortably across four en-suite bedrooms, or wander the expansive grounds dotted with trees and surrounded by olive groves.
Explore the 1018 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 Castiglione della Pescaia, Grosseto, 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 Castiglione della Pescaia Home to Rent with a Swimming Pool today, and set up a holiday to remember.
