Vines & Vistas
8 guests
4 bedrooms
Radda in Chianti, Tuscany
Nestled in the heart of the Chianti region, this charming cottage seamlessly blends traditional and modern styles. Surrounded by vineyards, olive groves, and oak forests, with views of the valley and distant castles, you can’t fail to relax here.
Shadow Blooms
4 guests
3 bedrooms
Castel del Piano, Grosseto
Tucked away in the Tuscan countryside just outside Castel del Piano, this rural villa is perfectly placed for exploring. This region is known for natural hot springs and idyllic spa towns like Saturnia and Montalcino – both a forty-minute drive away – where you can soak your troubles away in thermal pools.
Aglio e Olio
9 guests
5 bedrooms
Montepulciano, Siena
Tucked within seventy hectares of countryside and surrounded by countless rows of olive groves and cypress trees, this charming Tuscan estate is the picture of rural tranquillity. Split into the main house and an independent annexe, the address has retained plenty of its original features – wooden beams, an open-hearth fireplace, stone floors and antique furniture give guests a sense of history.
The Olive House
10 guests
5 bedrooms
Murlo, Siena
This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area.
Explore the 794 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. 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.
