
Holiday rentals in Calcione
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Top-rated holiday rentals in Calcione
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Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dinners. A memorable getaway awaits you in this little slice of paradise!
4.97 out of 5 average rating, 198 reviews
Villa Eleonora
Welcome to my farmhouse in the open countryside in the heart of Tuscany, a typical Leopoldina house built by Grand Duke Leopold of Tuscany during the Grand Duchy, with its typical square shape and turret. It is located 6 km from the village, in a quiet location. We will be delighted to offer you our pizza evenings, dinners with a private chef and cooking classes. From October to March, the annexe is rented separately from the main house. It is possible that there will be 2 people staying in the small separate building.
4.85 out of 5 average rating, 20 reviews
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
4.9 out of 5 average rating, 241 reviews
House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.
4.96 out of 5 average rating, 125 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 reviews
Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
4.93 out of 5 average rating, 334 reviews
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.
4.99 out of 5 average rating, 116 reviews
Unique Villa in Tuscany
La Smirandola is nestled in the hills between Siena and Arezzo. The house is surrounded by a large garden with olive grove. Next to the (heated) swimming pool, there is a gazebo where you can have lunch/dinner/grill. The house is spread over two floors: on the ground floor there is the kitchen, living room, veranda, bedroom and bathroom. On the first floor there are 3 bedrooms + 2 bathrooms. The kitchen is equipped with a dishwasher. Air conditioning available at a flat rate of: €20/day.
4.93 out of 5 average rating, 42 reviews
Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
4.96 out of 5 average rating, 116 reviews
Beautiful villa with pool in secluded location
Peace and tranquility in the stunning Villa L'Eremo, offering total seclusion in 25 acres of garden, olive grove and woodland. Relax by the pool, on a shaded terrace or meander through the gardens, breathing in the scent of lavender and rosemary. All this just 3kms from the lovely Monte San Savino, thankfully off the conventional tourist trail, yet offering many outstanding restaurants. Perfectly placed for exploring Tuscany, just 1hr from Florence and Perugia. Codice: 051025LTN0067
5.0 out of 5 average rating, 45 reviews
Sasso Canaldo Charming property in Tuscany
Sasso Canaldo is a magnificent property immersed in the Tuscan countryside that is divided into 4 houses: Villa sleeps 9, Lavanda 7, Limonaia 2+2, Roseto 2, total beds 22. Each house enjoys complete independence and autonomy. A structure particularly suitable for organizing events, family reunions, celebrating anniversaries and weddings. The large park allows for long walks in complete relaxation. Large swimming pool, recently completely renovated, surrounded by greenery.
5.0 out of 5 average rating, 6 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviewsPopular amenities for Calcione holiday rentals
Other great holiday rentals in Calcione

Il Podere - Rustic charm in Tuscany
5.0 out of 5 average rating, 10 reviews
Stunning Tuscan Villa & Panoramic Infinity Pool
5.0 out of 5 average rating, 96 reviews
Hadrian's Villa
5.0 out of 5 average rating, 4 reviews
Villa il Laghetto with Infinity Pool in Tuscany
4.96 out of 5 average rating, 56 reviews
Il Capoverso Farmhouse (9+5p.) Feel welcome
5.0 out of 5 average rating, 6 reviews
Incredible Views & Pool in the Tuscan Hills
4.85 out of 5 average rating, 26 reviews
Castello delle Serre – Private Villa
4.97 out of 5 average rating, 29 reviews
Magnificent 1700's villa in Tuscany
4.81 out of 5 average rating, 69 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Lake Bolsena
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino





