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Holiday houses in Città della Pieve

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Top-rated holiday rentals in Città della Pieve

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Top Guest favourite
A scenic view reveals a medieval village perched on a hillside, surrounded by lush greenery and rolling hills. The buildings display a blend of architectural styles, set against a clear blue sky, illustrating the charm of the Tuscan countryside.
Home in Cetona
4.96 out of 5 average rating, 102 reviews

Case Aneris, Tosca - The most beautiful view of Cetona!

The stories of four generations have unfolded in the Aneris Houses. Thanks to the care and commitment of Aneris' children, today the Houses are two apartments equipped with all comforts, in an ideal location to enjoy the village - a three-minute walk from the square and the historic center - and explore enchanting places, where culture, nature, food and wine, and relaxation have been watchwords for centuries. The view of the Tuscan countryside and the medieval heart of the village are priceless.

Top Guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 124 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 204 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top Guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 110 reviews

Casa Dolce Toscana~Suite&View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation,with panoramic views,immersed in the hills of Tuscany. Anoasis of peace perfect for those who want to relax and live an authentic experience. Located a few kilometers from Siena and Florence,our accommodation combines rustic charm with all modern comforts. it is in the heart of the historic center of the famous village of Cetona,below the castle ,overlooking the valley and the scent of Tuscany.

Top Guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano
5 out of 5 average rating, 483 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Top Guest favourite
A bright living space features a white table surrounded by colorful chairs. Large arched windows open to a view of the green landscape. A grey armchair and wooden sideboard enhance the room's inviting atmosphere, with natural light flooding in from multiple angles.
Home in Città della Pieve
4.98 out of 5 average rating, 100 reviews

The Terrace of Victory

La Terrazza di Vittoria is a delightful studio on one level surrounded by silence and greenery. It is located a few meters from the main house and just 2 km from Città della Pieve. The large garden surrounding the house is a natural terrace overlooking Lake Trasimeno. It is enriched by a pergola equipped with a table and barbecue available for your meals in total relaxation. Inside, in a 40 sqm space, there is a double bed, a sofa bed, a bathroom and an equipped kitchen.

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
4.97 out of 5 average rating, 137 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.

Top Guest favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Condo in Asciano
4.97 out of 5 average rating, 319 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 to 20 which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and Wi-Fi Strategic location for visiting Tuscany and Umbria.

Top Guest favourite
A welcoming living area features a seating arrangement with a neutral-toned sofa and decorative cushions. A table for two is set nearby, surrounded by blue wicker chairs. The space is enhanced by natural light streaming through glass doors and soft accents of greenery on the walls.
Townhouse in Città della Pieve
5 out of 5 average rating, 12 reviews

Heart of the Parish - Luxury H. with Spa for a fee

About this place Completely renovated medieval historical residence with private spa suite at an additional cost. Hot tub with chromotherapy, 4-in-1 Turkish hammam, massage chair, exposed beams, equipped kitchen. In the heart of Città della Pieve between Umbria-Tuscany. 2 levels, sleeps 4, 3 bathrooms. 2h from Florence/Rome. Luxury sanctuary for authentic wellness in medieval red village with panoramic views of Val di Chiana and Perugino masterpieces.

Guest favourite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona
4.96 out of 5 average rating, 142 reviews

Poggio dell'orso.Traditional Casale. Amazing views

Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

Top Guest favourite
Farm stay in Campiglia D'orcia
4.95 out of 5 average rating, 473 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Guest favourite
A living area is characterized by stone walls and wooden beams. A cozy beige sofa is positioned near a traditional fireplace, complemented by a television mounted on the wall. Fresh flowers are arranged in a decorative vase on a table, enhancing the warm ambiance.
Home in Cetona
4.92 out of 5 average rating, 438 reviews

Rosaspina - Poggio Alla Serra

Rosaspina is located in the open countryside a stone's throw from the historic center of the village of Cetona, on the slopes of the homonymous mountain, in the south of the Province of Siena. It is furnished with the typical taste of the country house with views of the village and the mountains.

Popular amenities for Città della Pieve holiday rentals

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Città della Pieve?

    Four-legged friends are welcome in Città della Pieve. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Città della Pieve?

    Città della Pieve has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Città della Pieve

  • Total holiday rentals

    Explore 20 holiday rentals in Città della Pieve

  • Nightly prices starting at

    Città della Pieve holiday rentals start at $61 AUD per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Città della Pieve holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Città della Pieve rentals

  • 4.9 Average rating

    Città della Pieve stays are highly rated by guests—averaging 4.9 out of 5!

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