A Rustic Reverie
4 guests
2 bedrooms
Sovicille, Tuscany
For a taste of authentic Tuscan living, this holiday home is a great choice. This apartment is one of six, renovated from a 15th-century structure by a historically conscious architect.
Rent Luxury Holiday Cottages in Castiglione della Pescaia
We selected the 54 homes worth renting in this location
Home spotlights in Castiglione della Pescaia
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.
Hillside Harvest
4 guests
2 bedrooms
Gaiole in Chianti, Siena
Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine.
Tuscan Haven
2 guests
2 bedrooms
Sovicille, Tuscany
Situated a short drive outside the bustling medieval city of Siena, this villa offers a true escape in the Tuscan countryside. Originally constructed as a watchtower, its 12th-century exterior has been updated with a stunning glass pavilion that offers 270-degree views of rolling Tuscan hills covered in cypress trees and olive groves.
We selected the top 3% holiday homes in Castiglione della Pescaia Cottages
Explore the 54 most perfect homes in our collection
View on map
Check upcoming rates & availability for Castiglione della Pescaia Cottages
Frequently asked questions
Similar destinations
Discover our curated collection of luxury holiday Cottages in Castiglione della Pescaia, Grosseto, Tuscany, Italy. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Castiglione della Pescaia Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.
Search our collection