Apartment vacation rentals in Pienza

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.

4.98 out of 5 average rating, 161 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 or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

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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.

4.98 out of 5 average rating, 164 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.

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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.

4.97 out of 5 average rating, 186 reviews

Casa Bonari - a paradise for the eyes

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

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Apartment in Castelnuovo Berardenga

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

4.94 out of 5 average rating, 182 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

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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.

4.91 out of 5 average rating, 301 reviews

I Tramonti di Eramo, downtown Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

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A modern kitchen and dining area are featured, with a sleek table and four chairs placed beneath warm lighting. Wooden beams create an inviting atmosphere. A comfortable chair sits in the foreground, while a window reveals greenery outside, enhancing the space's brightness.

4.99 out of 5 average rating, 108 reviews

At the Arch - In the Heart of the Val D'Orcia

Scopri il fascino autentico della Toscana soggiornando in un accogliente e curato appartamento all'ingresso del centro storico situato sulle mura della città di Pienza, nel cuore della splendida Val D'Orcia. Un rifugio perfetto per chi cerca relax, bellezza e atmosfera, circondato da uno dei paesaggi più iconici di Italia. L'appartamento, ideale fino a 3 ospiti, combina semplicità e confort per offrirti un soggiorno piacevole e rilassante.

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A cozy room features a spacious bed against a white wall, complemented by rustic wooden beams and an inviting reading chair. A dining table is set with floral arrangements and tableware. Natural light is seen streaming through the open door leading to the garden.

5 out of 5 average rating, 102 reviews

Casa Tórta - comfort room

Casa Tòrta consists of a bedroom, reading room and bathroom, perfect for a short stay or for long periods, having reception services available. In the historic center of Monticchiello, there is this building that dates back to 1200. The large double bed is located in the main room with a fireplace stove with ancient charm. In the brightest room a reading lounge, then the green bathroom with shower.

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4.99 out of 5 average rating, 117 reviews

The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.

Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

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Apartment in Monteroni d'Arbia

An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.

4.94 out of 5 average rating, 283 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

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A spacious suite features a comfortable bed with neutral-toned bedding, complemented by wooden beams overhead. A freestanding bathtub is positioned near the entrance. Soft lighting creates a calming ambiance, while the adjoining bathroom is accessible through a glass door, enhancing the airy feel of the space.

4.97 out of 5 average rating, 411 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

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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.

4.9 out of 5 average rating, 231 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.

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Apartment in Castiglioncello del Trinoro

The image captures a charming stone exterior framed by blooming flowers and greenery. A doorway with a blue grille leads into a historic building, while the gravel pathway invites exploration. Soft evening light enhances the warm tones of the stone walls.

5 out of 5 average rating, 363 reviews

Stunning Tuscan apartment in 14 Century Palazzo

L'appartamento si trova al terzo piano di un edificio risalente al 1400,il borgo di Castiglioncello del Trinoro risale al1100,si affaccia sulla val d'orcia con vista a 360 gradi.

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Popular amenities for Pienza apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.9 out of 5 average rating, 401 reviews

A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.

Apartment in Montalcino

Panoramic Country Suite Montalcino

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The spacious dining area features a rustic wooden table surrounded by chairs, harmonizing with exposed wooden beams above. A white cabinet and a radiator are visible, while the window offers a view of the outside landscape. Light-colored walls create a warm and welcoming ambiance.

4.97 out of 5 average rating, 266 reviews

Casa Ricci Apartment in a 14th-century building

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A warm and inviting open space features a wooden dining table surrounded by chairs, illuminated by natural light from several windows. A red sofa is positioned nearby, while a television and kitchen appliances, including a stove and oven, are visible in the background.

4.93 out of 5 average rating, 124 reviews

Casa Crociani - Amazing Pool & Free Parking

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An outdoor terrace is presented with a modern seating arrangement featuring two white cushioned chairs and a matching sofa surrounding a dark coffee table. The view captures the rooftops of Montepulciano, complemented by a clear blue sky and distant hills.

5 out of 5 average rating, 118 reviews

Dimora dell'Erbe - Rooftop Apartment

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A private terrace is furnished with a seating area, featuring a table and comfortable chairs. Potted flowers adorn the space, enhancing the views of the surrounding Tuscan countryside. The terracotta tiles and stones provide an inviting outdoor setting.

4.99 out of 5 average rating, 104 reviews

Magnificent 2 BR with Terrace and Air Conditioning

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Apartment in Castiglione d'Orcia

A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.

4.99 out of 5 average rating, 111 reviews

Mimosa Apartment - Poggio al Vento

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A spacious bedroom features a large bed dressed in a vibrant red and orange patterned coverlet. A wooden bedside table sits nearby, and a painting adorns the wall. Natural light filters in through a window with wooden shutters, highlighting the exposed wooden beams above.

4.94 out of 5 average rating, 103 reviews

Via del Bacio Uno (literally Kiss Street One)

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A scenic landscape unfolds with rolling green hills and lined cypress trees under a bright blue sky. A balcony railing frames the view, while vibrant grass is visible in the foreground. The serene beauty of the Tuscan countryside is captured peacefully.

4.92 out of 5 average rating, 105 reviews

La Casetta di Monticchiello with panoramic views

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Private apartment rentals

Apartment in Quercegrossa

A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.

4.97 out of 5 average rating, 77 reviews

Tuscany jem: The Chianti Farmer's House

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A spacious bedroom features a large bed with a textured white coverlet. Two nightstands with lamps flank the bed. A wooden clothing rack stands alongside a vintage mirror, and a colorful rug anchors the room. Natural light filters through the window, enhancing the neutral tones.

4.98 out of 5 average rating, 45 reviews

In the heart of Pienza, just 50 meters from the cathedral!

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Superhost

A view from an open window reveals a panoramic landscape of rolling green hills and trees, framed by rustic stone architecture. Distant mountains rise under a clear blue sky, completing a serene and expansive scene.

4.66 out of 5 average rating, 231 reviews

Artistic Pienza | Breathtaking Val d'Orcia View

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A serene terrace space is presented, featuring a round glass table surrounded by white iron chairs. Greenery and blooming flowers are placed in terracotta pots, complemented by a trellis above providing shade. A charming view of terracotta rooftops and clear blue sky is visible in the background.

5 out of 5 average rating, 57 reviews

Live Like a Local & Private Concierge Service

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4.98 out of 5 average rating, 112 reviews

The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.

Apartment in Siena

Luxury frescoed apartment in the historical center

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An aerial view captures a charming property surrounded by lush greenery and rolling hills. A rectangular swimming pool is situated in the garden, framed by tall cypress trees. The rustic buildings reflect traditional Tuscan architecture, enhancing the serene landscape that stretches into the distance.

4.82 out of 5 average rating, 34 reviews

Poggio ai Gelsi, Ginestra Lodge

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Superhost

4.88 out of 5 average rating, 50 reviews

Nobile Vineyards | Boho Chic | ‘Il Gelsomino’

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4.94 out of 5 average rating, 83 reviews

Apartment in Scrofiano

Bright Tuscany Apartment with view, balcony, A/C

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Apartment rentals with a hot tub

Apartment in San Giovanni d'Asso

A dining table is set with plates, glasses, and utensils, positioned near expansive glass doors. Natural light fills the space, revealing a view of the private patio and lush greenery beyond. A bowl rests at the center of the table, enhancing the dining experience.

5 out of 5 average rating, 8 reviews

Podere Ferranino #Fra Angelico Townhouse

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Apartment in Monteleone d'Orvieto

An indoor pool is surrounded by rustic stone walls and a vaulted brick ceiling. Soft lighting enhances the tranquil ambiance. A shallow section of the pool is visible, along with steps leading to another area. Cozy cushions are placed nearby, inviting relaxation.

4.96 out of 5 average rating, 85 reviews

Elegant historic Palazzo, views of Tuscan valley

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Superhost

A sunlit outdoor area features comfortable lounge chairs in vibrant colors beside a hot tub. Olive trees and shrubs surround the space, providing a serene backdrop. A gentle slope of green grass continues toward distant hills, enhancing the tranquil atmosphere.

Apartment in Montevarchi

4.88 out of 5 average rating, 105 reviews

Apartment with garden in the heart of Tuscany

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5 out of 5 average rating, 50 reviews

A spacious outdoor area features a framed view of rolling green hills in the distance. A swimming pool is visible, surrounded by grass, with a sunshade above a table and chairs. The peaceful landscape showcases the natural beauty of the Tuscan countryside.

Apartment in Castelmuzio

Beautiful Sunset Apartment

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4.96 out of 5 average rating, 55 reviews

Charm Suite with swimming pool

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4.98 out of 5 average rating, 107 reviews

The living area features a stylish design with a dark gray sofa and two deep red armchairs. A round glass table sits on a marble floor, enhanced by natural light from the two windows with light curtains. A decorative mirror and elegant light fixtures adorn the walls.

Apartment in Siena

Domus Nannini - L'Arco di Matteotti Spa

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An ancient stone well is positioned in the foreground, showcasing intricate carvings and a circular top. In the background, an impressive stone building features a tower and windows, accented by flags. The scene captures the historical charm of Montepulciano's central square under a clear blue sky.

4.93 out of 5 average rating, 153 reviews

Charming House in Montepulciano

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A bright kitchen area features modern white cabinetry and a wooden countertop, complemented by a dining table with four white chairs. Large windows allow natural light to fill the space, providing a scenic view of the outdoors. A patterned backsplash adds visual interest.