
Villa vacation rentals in Città di Castello
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Quick stats about villa rentals in Città di Castello

Nightly prices starting at
Città di Castello vacation rentals start at G$127,554 GYD per night before taxes and fees

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Città di Castello rentals

5 Average rating
Città di Castello stays are highly rated by guests—averaging 5 out of 5!
Top-rated villa rentals in Città di Castello
Guests agree: these villas are highly rated for location, cleanliness, and more.

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
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Wine Experience Villa in Montepulciano
🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.
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Charming Tuscan Villa with View forFamily&Friends
The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away
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Villa San Martino, on the Tuscany/ Umbria border
Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.
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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
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Tuscan Villa Luigina with Pool & Panoramic View
If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX
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A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.
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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.
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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.
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La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
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Torre Villa Belvedere Luxury & Relax with pool
"TORRE VILLA BELVEDERE" Wonderful 260-square-meter apartment in a villa with a 12th-century tower. Private pool (15 meters long and 5 meters wide), billiards, darts, large garden, 80-square-meter porch, barbecue, gym, and relaxation area inside the tower. Convenient private parking within the property. Strategically located, 12 km from Perugia, 4 km from the highway, it can comfortably accommodate up to 8 guests. 3 double bedrooms with private bathroom, TV, safe.
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Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
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Popular amenities for Città di Castello villa rentals
Private villa rentals

Villa Montanina - relax in esclusiva in Toscana
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Ortaglia di Sotto Farm
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Il Posto Umbria - full property with large pool
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Villa il Laghetto with Infinity Pool in Tuscany
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Villa Casanova - Private Pool & Garden in Umbria
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Fabulous Farmhouse with Pool & 360 Panoramic View
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Lake View Private Villa with Pool
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Casa Napoleone - Tuscan Villa w/ pool near Cortona
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Luxury villa rentals

Montepulciano Central Villa – Sauna & Jacuzzi
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Villa a Montepulciano con Piscina
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Poggio Ginepro Panoramic Villa in Assisi
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Podere Biagio | Rural Tuscan farmhouse with pool
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“Villa Lux Poggelleri” – a unique view of the Casentino
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Villa with garden. The Cardinal's Garden.
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Villa A Chiaraluna (Agritourism)
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Villa Antico Casale entire property exclusively
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Villa rentals with a pool

The Lazy Oak
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Gli sterpi
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Tuscany Country House with swimming pool
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Villa La Foce
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Private Villa with swimming Pool and Garden exclus
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Villa Aurora
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Villa Eleonora
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Villa La Pieve
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Destinations to explore
- Lake Trasimeno
- Misano World Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Del Chianti
- Palacongressi Della Riviera Di Rimini
- Frasassi Caves
- Basilica of St Francis
- Italia in Miniatura
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- La Scarzuola
- Oltremare
- Fiabilandia
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- Parco Naturale del Monte San Bartolo
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Gola del Furlo
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore





