The Tuscan Song
17 guests
8 bedrooms
Castiglion Fiorentino, Arezzo
If you’re in search of a traditional Tuscan escape, this home delivers a great solution. Just 10 kilometres from Cortona, this rustic sanctuary consists of three independent apartments (each with its own entrance) – making it a great option for groups and families.
Limestone & Antique
12 guests
6 bedrooms
Marciano della Chiana, Arezzo
Situated near Monte San Savino, this farmhouse invites guests to experience an authentic taste of the Tuscan countryside, including a complimentary wine tasting and a visit to the owner's winery. With a large garden and private swimming pool overlooking the vineyards and hills, you'll likely choose to spend much of your time out here taking in the surrounding scenery.
The Lucia
10 guests
5 bedrooms
Cortona, Arezzo
This quintessentially Italian home is nestled in the countryside just 5 kilometres from the beautiful town of Cortona. Days here can be spent hiking, cycling and exploring the historic hilltop towns of Tuscany.
Fresh As a Vine
11 guests
6 bedrooms
Montecchio, Castiglion Fiorentino
Overlooking the lush Chiana Valley, this former farmhouse boasts views you won’t be forgetting any time soon. There are plenty of spots to sit back and soak it all in, but the pergola’s one of our favourites, perched right next to the pool and offering plenty of room for dining alfresco.
Explore the 1864 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 Castiglion Fiorentino, Arezzo, 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 Castiglion Fiorentino Home to Rent with a Swimming Pool today, and set up a holiday to remember.
