If the idea of a holiday brings to you visuals of you sitting with your family by the poolside amidst unending views, then this 3-bedroom holiday home in Castiglion Fiorentino is a perfect pick for you. With a private swimming pool, an illuminated garden and enviable location, this property is ideal for a family of 6. You are just 4 km away from the town centre, while staying here. Nearest restaurants are 6 km away. If you enjoy cooking for family and friends, there is a well-equipped kitchen at your disposal. On the terrace, there is a barbecue and is therefore ideal for dining outside with a nice glass of local wine. Bedrooms are air-conditioned as well as heated to keep you comfortable. Parking is on-site. ChildrenÂ’s bed is available for the young oneÂ’s comfort.

This is a contemporary villa, with a large private swimming pool and spectacular views, located in Mammi. This 2-bedroom villa is a great choice for a family of 4 coming on a refreshing break. You can conveniently go to the town centre, 2 km away and enjoy eating Italian delicacies. Florence, Arezzo and Cortona are nearby to visit. Spending lovely evenings in the illuminated and furnished garden will make memorable memories. You can cook barbecue meal together, if not lounging indoors. Air conditioning as well as heating is available for your comfort. Parking is on-site. Kids can comfortably sleep here on the children’s bed. Public transport can be availed 2 km away from the villa. Nearest airport is at 90 km. Attention: 1 pet accepted, only if small (request in advance)

Located near Castiglion Fiorentino, this villa has 4 bedrooms and accommodates 8 people. This luxurious villa has a swimming pool and offers stunning views of the valley. It also features a wood oven where you can make your own pizzas, making this the perfect holiday home for a family vacation. The town centre is 4 km away and you can buy your daily groceries 1 km from here. The historic city of Cortona and Lake Traseimeno are also nearby and are worth a visit. The home has a garden with furniture and a terrace with barbecue. It is child-friendly and has a children’s bed. It offers bed linen and bath towels. The nearest airport is Perugia San Francesco d'Assisi - Umbria International Airport, 68 km away.

Nestled among olive groves and rolling vineyards, this charming farmhouse in Castiglion Fiorentino offers a serene escape into the heart of Tuscany. Perfect for families and small groups seeking space and privacy, the home is set within a peaceful rural estate where guests can unwind under the Tuscan sun and soak in the region’s timeless beauty. The farmhouse features a private terrace ideal for quiet mornings or evening aperitivos, while the spacious garden invites you to lounge with a book or share alfresco meals beside the barbecue. The shared swimming pool is the centerpiece of summer days—cool off with a refreshing dip, bask on a sun lounger, or simply take in the uninterrupted views of the surrounding countryside. Despite its secluded setting, the property is conveniently close to the town center—Castiglion Fiorentino is just 3 km away, where you’ll find quaint shops, weekly markets, and traditional trattorias. For a special meal out, try Ristorante Da Muzzicone for classic Tuscan flavors or Il Passaggio for refined dining with a view. History and culture lovers will appreciate the short drives to Arezzo (20 km) and Siena (70 km), both offering a wealth of medieval architecture, art treasures, and vibrant local life. Discover Renaissance frescoes, ancient Etruscan roots, and lively piazzas—all easily accessible from your countryside haven. Whether you're here to explore, relax, or enjoy quality time with loved ones, this farmhouse delivers an authentic Tuscan experience with comfort and charm.

This cozy and beautiful agriturismo is in Castiglione Fiorentino in the rolling hills with forests, vineyards and olive trees. There are a total of three apartments overlooking a spacious garden. The decor is classic Tuscan terracotta floors and wooden ceilings and wooden beams.   Each apartment has its own private terrace to enjoy and relax. There is a pizza oven and barbecue that guests can use. Ask the homeowner how you can make a pizza in the pizza oven! On request you can have breakfast or dinner. The home owner is an excellent cook so a Tuscan dinner at the agriturismo is a must. Natural products are used. The panoramic swimming pool is behind the apartments so the garden is quiet. The pool has a sun terrace with sun beds, umbrellas and a shower. There is also a part of the garden with play equipment for children. In the area you can walk and cycle. The agriturismo does organic farming and produces and sells wine, olive oil and vin santo. Further growing the agriturismo typical plants and shrubs. So if you want to buy a small olive tree and take it home as a souvenir, this is possible!

Nestled in the scenic Val di Chiana, this charming pet-friendly cottage near Castiglion Fiorentino is perfect for a relaxing Tuscan escape. Recently renovated, the farmhouse blends rustic elegance with modern comforts, making it ideal for up to 4 guests. Surrounded by nature and just 2 km from town, it offers an authentic Italian countryside experience. Inside, the home features two cozy bedrooms, a well-equipped kitchen, and a warm dining area. Amenities include central and floor heating, a satellite TV, washing machine, and WiFi. Step outside to enjoy a large fenced garden, a private swimming pool overlooking the valley, sun loungers, barbecue facilities, and even bicycles to explore the surroundings. Located just 1.5 km from Castiglion Fiorentino, you’ll find supermarkets, restaurants, and a train station for easy day trips. Discover nearby gems like Cortona (12 km) or enjoy local delights at traditional trattorias. This farmhouse is a peaceful haven with convenient access to Tuscany's best.

Non-independent holiday home in a charming Tuscan farmhouse set in the beautiful landscape of the Val di Chiana, just 2 km from the town of Castiglion Fiorentino. There is a large enclosed garden, parking and a shared swimming pool overlooking Castiglion Fiorentino and surrounded by lavender and rosemary bushes, olive groves and centuries-old oaks. The perfect place for a relaxing holiday, to enjoy the peace and quiet of the Tuscan countryside and the beauty of the many picturesque historic villages in the surrounding area. The property has been recently renovated to offer authentic and enchanting surroundings, without forgetting the comforts. In the nearby Castiglion Fiorentino (2 km) you can find all the services you need, moreover the property is only 10 minutes away from the railway station which will allow you to easily reach many places to visit during your holiday. Supermarket 500 m away

This cosy and pleasant farmhouse is located on the bright hills of Castiglion Fiorentino, amidst woods, vineyards and olive groves. There are a total of three flats overlooking the large garden. The décor is classic Tuscan, with terracotta floors and wooden ceilings. Each flat has a private terrace for relaxing in peace and quiet. There is a pizza oven and barbecue for guests' use. Ask the owner to teach you how to use the wood-fired oven to make pizza! Breakfast and dinner can be served on request. The owner of the house cooks very well, so if you get the chance, don't miss out on a Tuscan farmhouse dinner. Fresh produce is used. The swimming pool with a panoramic view is behind the flats, so it's very quiet in the garden. It also includes a solarium with sun loungers, parasols and a shower. Part of the garden has games for children. In the surroundings you can go for walks or bike rides. The farm cultivates typical plants and shrubs using organic methods and produces and sells wine, olive oil and vin santo, and if you wish, you can buy a small olive tree to take home!

This welcoming, pleasant farmhouse is located in the sunny hills of Castiglion Fiorentino, amidst woods, vineyards, and olive trees. There are three apartments in total, overlooking the large garden. _x000D_ _x000D_ The furnishings are traditionally Tuscan, with terracotta floors and wooden ceilings. _x000D_ _x000D_ Each apartment has a private terrace to relax in complete tranquillity. There is a pizza oven and a barbecue for guests to use. Breakfast or dinner can be provided on request. The owner of the house is a very good cook, so if you have the opportunity, enjoy a Tuscan dinner in a farmhouse. Fresh products are used. The swimming pool with panoramic views is behind the apartments, so it is very quiet in the garden, and it includes a solarium with deckchairs, parasols, and a shower. Part of the garden has games for children. You can go for walks or bicycle rides in the surrounding area. _x000D_ _x000D_ The farmhouse grows typical plants and shrubs using organic methods and produces and sells wine, olive oil, and vin santo, so, if you wish, you can even buy and take home a small olive tree as a souvenir! _x000D_

Perched on a scenic hillside in Castiglion Fiorentino, this authentic Tuscan villa offers sweeping views of the lush Val di Chio. Ideal for families or groups, the home combines rustic charm with modern comfort. Relax in your private garden or soak up the sun by the spacious pool, perfect for a peaceful escape in the heart of Tuscany. Inside, the villa features five inviting bedrooms, a cozy living room with a traditional fireplace, and a fully equipped kitchen with modern appliances. Dine together in the elegant dining room or unwind on the terrace. A fenced landscaped garden, barbecue, sun loungers, and ample parking complete the outdoor setup, while conveniences like a washing machine, ironing board, and multiple bathrooms ensure a comfortable stay. Just 6 km away, Castiglion Fiorentino offers delightful shops and authentic Italian dining. A scenic 2 km vineyard walk leads to a charming restaurant and grocery store in Santa Cristina. Steeped in history, Borgo Caprile once hosted noble families and still radiates timeless elegance, an ideal base for exploring Tuscany’s rich heritage.