Apartment vacation rentals in Pienza

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Top-rated apartment rentals in Pienza

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Top guest favorite

A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.

Apartment in Cortona

4.99 out of 5 average rating, 155 reviews

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

Top guest favorite

A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.

Apartment in Montepulciano

5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Top guest favorite

A spacious living area is showcased with large windows offering panoramic views of the surrounding hills. A dining table sits in the center, accompanied by chairs, while a comfortable seating arrangement is positioned nearby. Natural light fills the space, highlighting the earthy tones and wood accents.

Apartment in Montepulciano

4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2025 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Top guest favorite

The spacious living area features rustic wooden beams and terracotta tile flooring. A wooden dining table is accompanied by several chairs, while a cozy seating area with a sofa is positioned nearby. A stone fireplace adds a traditional touch, and large windows allow natural light to fill the space.

Apartment in Pienza

4.91 out of 5 average rating, 123 reviews

"L'Ovile" Apartment with a view of Val d'Orcia

In the countryside, along the panoramic road that leads from Pienza to Monticchiello, 2 km from Pienza, large studio divided into sleeping area, with double and single bed, living-dining area, kitchenette, bathroom. Veranda for outdoor dining and relaxation. Panoramic view of Val d'Orcia and its villages. A few kilometers from Montepulciano and Montalcino, and the Bagno Vignoni hot springs. From June to September PRIVATE SWIMMING POOL There is NO breakfast service

Top guest favorite

A serene outdoor space is highlighted by a sparkling swimming pool surrounded by lush garden beds filled with vibrant flowers. Comfortable sun loungers are positioned under shaded umbrellas, offering a relaxing area. The historic building in the background complements the scenic countryside.

Apartment in Laviano

4.95 out of 5 average rating, 141 reviews

Farmhouse with swimming pool with wonderful view

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests eight vacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

Guest favorite

A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.

Apartment in Montepulciano

4.94 out of 5 average rating, 196 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historical center offers a breathtaking view of the surrounding countryside, giving an authentic and unforgettable experience. You can leave the house and taste the historic atmosphere of Montepulciano. Within walking distance you will have the extraordinary Piazza Grande, high quality restaurants and services of all kinds. Tuscany awaits you to experience unique emotions.

Top guest favorite

A wooden table is set with two cream-colored cups and a small vase filled with dried wheat and decorative grasses. The white brick wall creates a warm backdrop, enhancing the inviting atmosphere of the dining area.

Apartment in Montepulciano

4.99 out of 5 average rating, 263 reviews

Montepulciano Downtown Storico

Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. Apartment consists of: entrance hall, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

Guest favorite

A rustic dining area features a spacious table set with plates and glassware, surrounded by wooden chairs. Exposed beams highlight the ceiling, while a soft lamp provides gentle illumination. A glimpse of the outside view can be seen through the window, enhancing the inviting atmosphere.

Apartment in Montepulciano

4.91 out of 5 average rating, 129 reviews

Tuscany on the terrace, downtown Montepulciano

Welcome to Montepulciano, the hidden gem of Tuscany, where historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region. Immersed in the charming labyrinth of cobblestone streets, you will be greeted by the reassuring sound of bell towers announcing the passage of time, while the inviting scent of freshly baked bread mixes with the aromatic notes of our vineyards.

Top guest favorite

A spacious bedroom features a comfortable bed with a soft grey headboard and neutral bedding. A small dining area with a wooden table and two dishes is visible. A large mirror and a flat-screen TV are mounted on the wall, reflecting natural light from a nearby window.

Apartment in Sinalunga

4.99 out of 5 average rating, 275 reviews

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

Guest favorite

Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.

Apartment in Monticchiello

4.97 out of 5 average rating, 153 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

Top guest favorite

A charming street is lined with stone buildings, featuring planters with greenery. A clock tower rises in the distance, reflected in puddles on the cobblestone surface. The scene is enhanced by a soft overcast sky, suggesting a quaint atmosphere.

Apartment in Pienza

4.82 out of 5 average rating, 212 reviews

Comfortable and quiet in Pienza

Small but comfortable apartment located in a private courtyard a few dozen meters from the main door of Pienza. Completely independent, with terrace, equipped kitchen, and Wi-Fi. I remind those who use public transport that on Sundays there are no buses, only taxi service. I remind those who use public transport that on Sundays there are no buses, only taxis.