Holiday houses in Orzale

Villa Garden of the Jars

In an enchanting hilly location, located between the characteristic Tuscan towns of Cortona and Castiglion Fiorentino, is Il Giardino delle Giare. A completely independent farmhouse, surrounded by greenery, ideal for those seeking privacy and tranquility. The Villa, ideal for 4 people, is equipped with every comfort. The living area consists of a nice living room with sofas and TV, a spacious dining room, a fully equipped kitchen and a full bathroom, equipped with a shower. The sleeping area consists of two elegant double bedrooms and a bathroom. The true soul of this lovely property is the beautiful flower garden, cared for in every detail. The swimming pool overlooks the valley, thanks to its suggestive location. You can enjoy refreshing baths and relax in the sun, looking out to the horizon. The garden has a relaxation area around the pool and a fully equipped dining area for outdoor dining, ideal for excellent barbecues or for cooking a tasty pizza in the wood oven. Guests will have a large private parking lot at their disposal. A stay at Il Giardino delle Giare will give you an unforgettable vacation in a charming and exclusive location

Family · Location · Kitchen

Tuscan charm of villa - countryside - Villa Senaia

In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Value · Location · TV

Tuscany Villa Mammi

Large, renovated stone villa in the woods of Castiglion Fiorentino, close to Cortona, Arezzo and Siena. A haven of privacy featuring a swimming pool, a panoramic hot tub with breathtaking views of the valley, and table tennis. Enjoy magical evenings under the stars, thanks to the authentic stone barbecue and the wood-fired pizza oven. The ideal getaway for those seeking relaxation, nature and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable holiday.

Family · Location · Hot tub

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

Location · Value · Getting around

Casa Napoleone - Tuscan Villa w/ pool near Cortona

A villa set on a hill, overlooking a magnificent Tuscan valley, yet only 10 mins drive from Castiglion Fiorentino train station. A 20 min drive from Arezzo and Cortona, a town made famous by the book and movie “Under The Tuscan Sun”. The Villa is the perfect base and within striking distance of Florence, Siena, Assisi and Montepulciano, famous for its Brunello wine, either by car or train. And after all that exploration you’ll return to soak in the pool whilst enjoying the stunning views.

Location · Family · Getting around

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Family · Value · Decor

Villa Tonacato - Charming Villa with private pool

Ancient rural farmhouse, located on the Tuscan hills with views of the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system

Location · Value · Hospitality

Beautiful and cozy country-house, sleeps 11

Exquisite two-storey villa with open-plan living and dining areas and five bedrooms overlooking the pool and countryside. Ideal for families or friends, with generous indoor and outdoor spaces. A private courtyard opens onto a beautiful pool and two dining areas set among olive trees. The main building features a private spa with chromotherapy shower and infrared sauna with red light. Pool heating available on request. Designed for relaxation, wellness and shared moments.

Location · Family · Kitchen

Villa with Private Pool in the Tuscan Countryside

Modern villa with private pool, waterfall, large garden and relaxation area. Divided into: Suite with hydromassage bathtub, private bathroom and small refreshment corner; Apartment with 2 bedrooms, equipped kitchen and a second bathroom in elegant white faux marble. Perfect for families and groups up to 7. Features American BBQ, panoramic gazebo, ping pong, outdoor dining area and poolside shower. Close to Cortona, Arezzo, Montepulciano, Siena and the Crete Senesi.

Family · Location · Pets

Ortaglia di Sotto Farm

Located in the Tuscan countryside, a 10-minute drive from Castiglion Fiorentino, Podere Ortaglia di Sotto offers a private pool with enclosed garden, WiFi and free private parking. The holiday home features 5 bedrooms, 6 bathrooms, a flat-screen TV, a dining area, a fully equipped kitchen and a terrace with mountain and valley views.(The swimming pool is available from 23 May to 17 October, closing and opening dates may vary depending on the weather)

Family · Location · Backyard

Villa Pergo is an ancient charming country villa

Stay in a piece of Tuscan history at Villa Pergo, a charming countryside estate dating back to 1640. Surrounded by olive groves and rolling hills near Cortona, the villa offers authentic character, panoramic views, and a beautiful infinity pool. With space for up to 11+1 guests in 6 bedrooms, large gardens and peaceful surroundings, it is the perfect retreat for families or groups looking to experience the true charm of Tuscany.

Family · Location · Hiking

Charming Cottage with Pool

This charming cottage with pool is nestled in the heart of the beautiful Val di Chiana, a few minutes’ drive from the picturesque hilltop town of Castiglion Fiorentino and 15 minutes from Cortona. Here you can enjoy the peace of the Tuscan countryside. The large swimming pool (12.00 x 6.00 m) is for exclusive use of the guests. During summer 2026 the pool is open May 16th - October 3th

Location · Family · Barbecue