
Villa holiday 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 holiday rentals start at $1,065 NZD per night before taxes and fees

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
ValueLocationOutdoor spaces
4.9 out of 5 average rating, 241 reviews
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.
LocationValueBarbecue
4.97 out of 5 average rating, 126 reviews
Torre Villa Belvedere Luxury & Relax with pool
"TORRE VILLA BELVEDERE" Wonderful 260 square meter apartment in a villa with a 12th century tower. Private swimming 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. Located in a strategic position, 12 km from Perugia and 4 km from the highway, it can comfortably accommodate up to 8 guests with 3 double bedrooms with private bathrooms, TV, and a safe.
FamilyLocationLong stay
5.0 out of 5 average rating, 114 reviews
Charming Tuscan Villa in Val d'Orcia with a view
Luxury and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!
ValueLocationCheckout
4.97 out of 5 average rating, 130 reviews
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.
LocationFamilyAccuracy
4.9 out of 5 average rating, 59 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
LocationFamilyComfort
4.93 out of 5 average rating, 334 reviews
Villa in Montepulciano with a Pool
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * 2 AirCon units: 1 per bedroom * * Pool open from April to November. Circular warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *
LocationFamilyComfort
4.92 out of 5 average rating, 148 reviews
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.
LocationValuePets
5.0 out of 5 average rating, 96 reviews
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.
ValueLocationBarbecue
4.96 out of 5 average rating, 102 reviews
Fabulous Farmhouse with Pool & 360 Panoramic View
In the very centre of Italy, straddling the border of Umbria and Tuscany, this carefully restored farmhouse makes a great base for a memorable Italian holiday. Situated in an idyllic hillside position overlooking Montepulciano, ‘La Colomba’ is blessed with 360-degree views of iconic Italian landscape and fully equipped with all child amenities. Within easy reach of many of the world’s most important historical and cultural attractions, this house really is The Italian Dream.
LocationFamilyAmenities
4.92 out of 5 average rating, 61 reviews
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.
LocationValueGetting around
4.97 out of 5 average rating, 159 reviews
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 pool is available from the last week of May to the second week of October .The dates may vary depending on the weather.)
LocationFamilyCondition
4.95 out of 5 average rating, 19 reviewsPopular amenities for Città di Castello villa rentals
Private villa rentals

Villa del Duca - Private villa with pool
FamilyLocationHot tub
4.94 out of 5 average rating, 18 reviews
Casa Napoleone - Tuscan Villa w/ pool near Cortona
FamilyLocationKitchen
4.96 out of 5 average rating, 28 reviews
romignano wine farm
FamilyValueAmenities
4.74 out of 5 average rating, 57 reviews
Villa il Laghetto with Infinity Pool in Tuscany
ValueFamilyNearby
4.96 out of 5 average rating, 56 reviews
Villa Montanina - exclusive relaxation in Tuscany
LocationFamilyBeach
4.99 out of 5 average rating, 85 reviews
Il Posto Umbria - full property with large pool
LocationFamilyNearby
5.0 out of 5 average rating, 9 reviews
Lake View Private Villa with Pool
LocationFamilyNearby
4.92 out of 5 average rating, 51 reviews
Villa Casanova - Private Pool & Garden in Umbria
FamilyLocationCleanliness
4.95 out of 5 average rating, 20 reviewsLuxury villa rentals

Tuscan Villa Luigina with Pool & Panoramic View
LocationFamilyGetting around
4.8 out of 5 average rating, 110 reviews
Montepulciano Central Villa - Sauna & Jacuzzi
FamilyLocationCheckout
4.85 out of 5 average rating, 153 reviews
Villa with garden. The Cardinal's Garden.
LocationFamilyIndoor spaces
4.97 out of 5 average rating, 97 reviews
Poggio Ginepro Panoramic Villa in Assisi
FamilyLocationAmenities
4.96 out of 5 average rating, 46 reviews
Villa A Chiaraluna (Agritourism)
LocationValueWalkability
4.9 out of 5 average rating, 40 reviews
Villa La Pieve
FamilyLocationHiking
4.67 out of 5 average rating, 36 reviews
Villa Le Vigne, 8 pax, private pool, Top Comfort
ValueFamilyLayout
4.91 out of 5 average rating, 91 reviews
Tuscany Country House with swimming pool
FamilyValueCondition
4.95 out of 5 average rating, 75 reviewsVilla rentals with a pool

Villa Il Giardino di Diana (12 people)
LocationFamilyComfort
4.96 out of 5 average rating, 48 reviews
Villa Aurora
FamilyValueLong stay
4.97 out of 5 average rating, 67 reviews
Villa Eleonora
FamilyLocationKitchen
4.85 out of 5 average rating, 20 reviews
Casale Santa Margherita in beautiful Assisi
ValueFamilyCleanliness
4.92 out of 5 average rating, 52 reviews
Private Villa with swimming Pool and Garden exclus
FamilyLocationComfort
4.9 out of 5 average rating, 30 reviews
Villa Antico Casale entire property exclusively
LocationFamilySleep quality
4.94 out of 5 average rating, 32 reviews
Terra Antica Suites & Villas - Montepulciano
LocationFamilyAccuracy
5.0 out of 5 average rating, 55 reviews
Apt. Rolando-Tenuta VillaAugusto
FamilyLocationShared spaces
4.97 out of 5 average rating, 34 reviewsDestinations to explore
- Lake Trasimeno
- Misano World Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Del Chianti
- Palacongressi Della Riviera Di Rimini
- Basilica of St Francis
- Frasassi Caves
- Italia in Miniatura
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- La Scarzuola
- Siena Cathedral
- Fiabilandia
- Oltremare
- Parco Naturale del Monte San Bartolo
- Avignonesi Winery Fattoria Le Capezzine
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Gola del Furlo
- Terme San Filippo
- Abbey of Sant'Antimo
- Castello di Gradara





