Castiglione dei Pepoli Villas - Best Villa Castiglione dei Pepoli 2026

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Our top choices for Castiglione dei Pepoli villas

A spa area with a hot tub, wicker seating, and a glass enclosure overlooking a garden.

1. Modern Villa with heated jacuzzi,sauna,panoramic view,close to Tuscany

Pergoloso

Andy C.

includes taxes & fees

14 Nov - 15 Nov

2. VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

Pontassieve

"This place is magical!!!!! The host was amazing and so communicative - readily available on the property and was able to answer questions as well as drive us to get food in town and to the train station! Ample space for guests and the property is beautiful. The pool area is great and comes with fun floats / fun activities for near the pool. The ambiance of the outdoor dining area is lovely and the check in/out process was easy. Couldn’t recommend this place more!!!"

Lyndsey S.

includes taxes & fees

14 Nov - 15 Nov

A balcony with a table and chairs, a view of a mountainous landscape, and a door leading outside.

3. Villa 'Casa Padronale Podere La Carbonaia' with Private Terrace, Shared Garden and Wi-Fi

Vicchio

includes taxes & fees

13 Dec - 14 Dec

A table with a vase of flowers on a balcony overlooking a mountainous landscape.

4. Villanova sul Molino Lonciano with Private Pool, Wi-Fi, and Air Conditioning

Sesto Fiorentino

includes taxes & fees

15 Nov - 16 Nov

A terrace with a table and chairs, surrounded by a wrought iron fence and climbing plants.

5. Villa 'Ancòra Tenuta Lonciano' with pool and view

Sesto Fiorentino

"We had a wonderful time at Villa Ancora. From the time I booked Antonella (our host) was so engaged and friendly. She met us at the property and made sure we had everything we needed. She gave us great advice on local markets, restaurants and ideas to make the most of our vacation. We enjoyed every aspect of the beautiful property from the cozy beds to the well-appointed kitchen, the stunning view and comfortable pool area. "

Guillermo S.

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with lounge chairs and a view of the sunset over a hilly landscape.

6. Villa La Torre Tenuta Lonciano with Private Pool, AC, and Sauna

Sesto Fiorentino

includes taxes & fees

15 Nov - 16 Nov

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Learn more about Castiglione dei Pepoli

Tucked into the Apennine Mountains, this medieval village offers charming piazzas and the impressive Church of San Lorenzo with its Renaissance artworks. Hike the surrounding forest trails or time your visit for the autumn mushroom festival when locals celebrate the region's prized porcini harvest.

See all hotels in Castiglione dei Pepoli

A historic building with arched walkways and a lush green courtyard.

Top reviews in Castiglione dei Pepoli

A stone building with a balcony, surrounded by a gravel driveway and flower beds.

Fattoria Ca' di Fatino

Castiglione dei Pepoli

10/10 Excellent

Superlative. The setting is magnificent, nestled in the hills with sensational sweeping views. It’s a restored 1780s farmhouse run by a Swiss-Italian couple, who treat their guests like family. More like the families on old TV shows. It’s a working farm with dozens of horses, 3 dogs, a cat, and a handful of chickens (whose fresh eggs are served every morning). Everything is clean, comfortable, and well appointed, but don’t come here looking for plush. About 200m away is an unassuming...