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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 $1,035 NZD 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.

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Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

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

ValueFamilyComfort

4.9 out of 5 average rating, 240 reviews
Top Guest favourite
Villa in Montepulciano

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.

LocationFamilyHot tub

4.97 out of 5 average rating, 125 reviews
Top Guest favourite
Villa in Colombella

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.

LocationFamilyBreakfast

5.0 out of 5 average rating, 114 reviews
Top Guest favourite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme

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

FamilyLocationKitchen

4.97 out of 5 average rating, 128 reviews
Superhost
A saltwater swimming pool is framed by lush greenery, with sunbeds positioned on the grass nearby. A natural fence enhances the privacy of the outdoor area, which is surrounded by trees that provide shade and a serene environment.
Villa in Pierle

Historic Villa Getaway with 6BR/9BA, Pool, Views

This six-bedroom villa complex, set in atop a hill, overlooks a panorama of surrounding hills, fully immersed in nature. Villa was estored in 2020, with the rustic flair preserved to maintain its unique charm. The authentic stonework, the open fireplace in the entrance hall, and the exposed beams are in harmony with wooden floors. The villa is within 30min drive of Cortona. Also near Siena, Gubbio, Assisi, Lake Trasimeno, Arezzo, Montepulciano, Spoleto, and Perugia. (Read other details to note)

LocationValueGetting around

4.89 out of 5 average rating, 46 reviews
Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

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

LocationValueIndoor spaces

4.92 out of 5 average rating, 331 reviews
Top Guest favourite
Villa in Cortona

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

LocationFamilyOutdoor spaces

4.81 out of 5 average rating, 108 reviews
Guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano

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.

LocationFamilyKitchen

4.96 out of 5 average rating, 166 reviews
Top Guest favourite
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona

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.

ValueLocationLong stay

5.0 out of 5 average rating, 96 reviews
Top Guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

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.

ValueLocationAccuracy

4.96 out of 5 average rating, 101 reviews
Top Guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino

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

FamilyValueLong stay

4.99 out of 5 average rating, 107 reviews
Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

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.

FamilyValueKitchen

4.97 out of 5 average rating, 158 reviews

Popular amenities for Città di Castello villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top Guest favourite
A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.
Villa in Castiglion Fiorentino

Tuscany Villa Mammi

FamilyValueComfort

4.99 out of 5 average rating, 89 reviews
Guest favourite
An aerial view captures a large hilltop property surrounded by lush greenery, with a spacious pool at its center. Two rustic buildings, with traditional tiled roofs, sit amidst olive trees, and expansive hills stretch into the distance under a clear blue sky.
Villa in Umbertide

Il Posto Umbria - full property with large pool

FamilyLocationCondition

5.0 out of 5 average rating, 8 reviews
Guest favourite
The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.
Villa in Castiglion Fiorentino

Ortaglia di Sotto Farm

LocationFamilyComfort

4.95 out of 5 average rating, 19 reviews
Guest favourite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo

Fabulous Farmhouse with Pool & 360 Panoramic View

LocationFamilyHeating

4.91 out of 5 average rating, 58 reviews
Top Guest favourite
The villa is surrounded by lush greenery, showcasing an inviting infinity pool that reflects the sky. The stone exterior of the house features warm wooden shutters, with outdoor seating visible on the terrace. Nearby, lavender plants create a serene ambiance against the landscape.
Villa in Lisciano Niccone

Villa San Martino, on the Tuscany/ Umbria border

FamilyLocationAir conditioning

4.89 out of 5 average rating, 58 reviews
Top Guest favourite
The image features a serene outdoor area with a spacious swimming pool surrounded by lounge chairs. Lush greenery and flowering plants line the poolside, while a stone wall and distant hills provide a peaceful backdrop under a clear sky.
Villa in Pieve a Socana

Villa Montanina - exclusive relaxation in Tuscany

ValueFamilyBeach

4.99 out of 5 average rating, 83 reviews
Top Guest favourite
Villa in Arezzo

Casa Napoleone - Tuscan Villa w/ pool near Cortona

FamilyLocationBarbecue

4.96 out of 5 average rating, 27 reviews
Guest favourite
A shaded outdoor seating area features a white sofa and black wicker chairs, facing a view of Lake Trasimeno. A small table holds drinks, while vibrant sunflowers are arranged nearby. The pool is visible in the background, surrounded by lush greenery.
Villa in La Cima

Lake View Private Villa with Pool

FamilyLocationGetting around

4.92 out of 5 average rating, 49 reviews

Luxury villa rentals

Guest favourite
Villa in Montepulciano

Villa in Montepulciano with a Pool

ValueLocationHospitality

4.92 out of 5 average rating, 146 reviews
Guest favourite
Villa in Montepulciano

Montepulciano Central Villa - Sauna & Jacuzzi

LocationValueCheckout

4.85 out of 5 average rating, 153 reviews
Top Guest favourite
A spacious swimming pool is surrounded by well-maintained gardens with lush greenery and tall trees. Comfortable loungers are positioned on the pool deck, and an umbrella provides shade nearby. The tranquil setting offers views of the adjacent hills and landscape.
Villa in Assisi

Poggio Ginepro Panoramic Villa in Assisi

LocationFamilyKitchen

4.96 out of 5 average rating, 46 reviews
Top Guest favourite
The aerial view captures the charming layout of Monticchiello, showcasing terracotta-roofed buildings surrounding a lush green garden adorned with soft lighting. A winding pathway leads to the garden, providing a serene outdoor area amidst the medieval architecture.
Villa in Monticchiello

Villa with garden. The Cardinal's Garden.

LocationFamilySleep quality

4.98 out of 5 average rating, 95 reviews
Top Guest favourite
The image captures a tranquil scene of a swimming pool reflecting the colors of a sunset, surrounded by trees and hills. The serene water mirrors the sky’s hues, with the sun positioned just above the mountains in the distance, evoking a peaceful atmosphere.
Villa in Poppi

“Villa Lux Poggelleri”: a unique view of the Casentino

FamilyLocationComfort

5.0 out of 5 average rating, 24 reviews
Guest favourite
Surrounded by lush greenery, the villa is set amidst gentle hills. An infinity pool sits at the edge of the property, complemented by sun loungers and an umbrella. The traditional stone structure is nestled among the trees, enhancing the serene environment.
Villa in Resina, Perugia

Villa Antorrita Farmhouse, infinity pool, ensuite

FamilyLocationSleep quality

4.97 out of 5 average rating, 61 reviews
Guest favourite
A rustic stone villa is surrounded by lush greenery and tall cypress trees under a clear blue sky. The spacious exterior features multiple arched windows and a welcoming porch, with outdoor seating visible in the front garden.
Villa in Ranciano

Villa A Chiaraluna (Agritourism)

ValueLocationOutdoor spaces

4.9 out of 5 average rating, 40 reviews
Guest favourite
A rustic Tuscan farmhouse is surrounded by lush green vineyards, with a private pool visible in the grassy area. The structure features a mix of stone and terracotta, harmonizing with its natural landscape.
Villa in Cortona

Villa Le Vigne, 8 pax, private pool, Top Comfort

ValueFamilyAmenities

4.91 out of 5 average rating, 91 reviews

Villa rentals with a pool

Top Guest favourite
A charming stone cottage is set among lush green hills, featuring large arched windows and a shaded patio area with outdoor seating. Olive trees surround the property, providing a connection to the natural landscape, while a gravel pathway leads to the entrance.
Villa in Sinalunga

The twigs

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 97 reviews
Guest favourite
Two cocktails with fresh fruit adorn a table. A straw hat rests nearby, while a serene view of a pool and rolling hills unfolds in the background, under a clear blue sky.
Villa in Urbania

Villa del Duca - Private villa with pool

FamilyLocationKitchen

4.94 out of 5 average rating, 17 reviews
Guest favourite
A private swimming pool is surrounded by a well-maintained garden, with lounge chairs positioned nearby. The two-story ancient stone building features a tiled roof and multiple outdoor seating areas, framed by trees and sun umbrellas, creating an inviting outdoor space.
Villa in Panicale

Villa Antico Casale entire property exclusively

FamilyLocationIndoor spaces

4.94 out of 5 average rating, 32 reviews
Top Guest favourite
A charming brick farmhouse is framed by olive trees and lush gardens, providing a serene backdrop for the inviting pool. Sun loungers and umbrellas are arranged around the pool area, creating a relaxing outdoor space for guests to unwind.
Villa in Cortona

Villa Il Giardino di Diana (12 people)

FamilyLocationWalkability

4.96 out of 5 average rating, 46 reviews
Superhost
A private swimming pool is surrounded by green lawn and well-maintained landscaping. Adjustable loungers sit beside the water, while a shaded umbrella provides relief from the sun. The villa, partially hidden by trees, offers a tranquil backdrop to the serene outdoor space.
Villa in Chiusi Scalo

Private Villa with swimming Pool and Garden exclus

FamilyValueOutdoor spaces

4.9 out of 5 average rating, 30 reviews
Guest favourite
The spacious kitchen and dining area features rustic wooden beams and well-lit windows that invite natural light. A large dining table is surrounded by white chairs, accommodating several guests. An inviting seating area with a sofa and decorative elements enhances the communal atmosphere.
Villa in Arezzo

Tuscany Country House with swimming pool

LocationValueHospitality

4.95 out of 5 average rating, 73 reviews
Guest favourite
A charming stone house is framed by vibrant flower pots filled with pink blooms. Sun loungers are positioned nearby, leading to a spacious pool area surrounded by lush greenery. Natural stone pathways enhance the outdoor setting under clear blue skies.
Villa in La Cima

Villa Aurora

ValueLocationCondition

4.97 out of 5 average rating, 66 reviews
Top Guest favourite
A spacious outdoor area features a large swimming pool surrounded by a manicured lawn. Sun loungers and umbrellas are arranged along the poolside, with trees providing natural shade in the background. A gazebo is also present, enhancing the relaxing ambiance of the space.
Villa in Camucia

Apt. Rolando-Tenuta VillaAugusto

LocationValueCondition

4.97 out of 5 average rating, 33 reviews

Destinations to explore