Vacation rentals in La Strada-Santa Cristina

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

Location · Family · Quiet

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.

Value · Family · Air conditioning

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 · Nearby

Tuscany Villa Mammi

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

Value · Family · Check-in

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 · Sleep quality

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.

Value · Family · Kitchen

Casa Bianchini | Duplex 6-bedroom apartment (12 +1

La Foresteria is a historical rural estate located near Arezzo in southeast Tuscany. Surrounded by lush countryside and fruit orchards, it offers guests serenity and peace. The property features ten carefully restored apartments, a private swimming pool, and an on-site restaurant where guests can enjoy breakfast and dinner. Its location is perfect for relaxing or exploring Tuscany’s art, culture, and nearby cities like Cortona, Florence, Siena, and Montepulciano.

Family · Value · Shared spaces

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 · Amenities

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 · Amenities

Villa il Laghetto with Infinity Pool in Tuscany

PERFECT LOCATION FOR YOUR WEDDING, SPECIAL EVENTS & PRIVATE PARTY! PAY ATTENTION: You can book Food&Wine services such as Chef in Villa, Cooking Class and delivery shopping. The ideal location to spend days in the tranquillity of a natural oasis with breathtaking views. It's divided in a main building and a dependance, it offers pool and Jacuzzi (not hot)

Location · Value · Getting around

Coaching House

The Villa is situated in an ancient country building located in Arezzo, twenty minutes walk from the historic center and surrounded by shops, supermarkets, restaurants within a few minutes walk. By car you reach the downtown and the treain station in about 10 minutes; moreover, the structure is close to places of interest such as the Equestrian Centre.

Family · Location · Pool

Tuscany House | View Breathtaking

Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.

Family · Location · Biking