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Apartment holiday rentals in Castiglione d'Orcia

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Top-rated apartment rentals in Castiglione d'Orcia

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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

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

4.98 out of 5 average rating, 163 reviews
Top Guest favourite
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

Casa Bonari - a paradise for the eyes

Casa Bonari is a self-contained, non-shared, single-storey apartment located within a villa at the foot of Monticchiello. It features 3 bedrooms, 2 bathrooms, a fully equipped kitchen and a living room. The rooms are furnished in Tuscan style, featuring restored heirloom 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 the rooms offer a beautiful view of the countryside.

4.97 out of 5 average rating, 187 reviews
Top Guest favourite
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.
Apartment in Castiglione d'Orcia

Mimosa Apartment - Poggio al Vento

Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

4.99 out of 5 average rating, 112 reviews
Guest favourite
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

I Tramonti di Eramo, central 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.

4.91 out of 5 average rating, 304 reviews
Top Guest favourite
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.
Apartment in Monticchiello

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.

5.0 out of 5 average rating, 104 reviews
Top Guest favourite
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.

4.99 out of 5 average rating, 117 reviews
Guest favourite
A panoramic view of a rustic farmhouse is captured, surrounded by expansive green hills and fields under a bright blue sky. The structure features a traditional tiled roof and is set within a serene countryside landscape, offering a tranquil escape.
Apartment in Castiglione d'Orcia

"il poderuccio" two-room farmhouse

The IL PODERUCCIO farmhouse has several apartments, for a total of 11 beds, including: a two-room apartment on the ground floor (sleeps 2) complete with double bedroom, private bathroom with shower and living room with double sofa bed, wood-burning fireplace and fully equipped kitchen. A truly comfortable environment, ideal for couples.

4.92 out of 5 average rating, 118 reviews
Top Guest favourite
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

Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.

4.9 out of 5 average rating, 404 reviews
Guest favourite
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.
Apartment in Monticchiello

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 ...

4.97 out of 5 average rating, 411 reviews
Superhost
Apartment in Castiglione d'Orcia

La Pineta: CIPRESSO, two-room apartment in Val D'orcia

Two-room apartment near the historic center of Castiglione d'Orcia with independent entrance, en-suite bathroom and parking space. Possibility to use a gazebo overlooking the Valdorcia and a BBQ in the common area (shared with other guests).

4.87 out of 5 average rating, 263 reviews
Top Guest favourite
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

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.

4.91 out of 5 average rating, 235 reviews
Top Guest favourite
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.
Apartment in Castiglioncello del Trinoro

Stunning Tuscan apartment in 14 Century Palazzo

The apartment is on the third floor of a building dating back to 1400, the village of Castiglioncello del Trinoro dates back to 1100, overlooking the Val d'Orcia with 360-degree views.

5.0 out of 5 average rating, 364 reviews

Popular amenities for Castiglione d'Orcia apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favourite
A rustic stone building is framed by lush greenery, with a gravel pathway leading to its entrance. Windows are adorned with flower boxes, and archways add architectural interest. The sky features a mix of clouds, hinting at a temperate climate.
Apartment in Montalcino

Classic two-room apartment

4.84 out of 5 average rating, 105 reviews
Top Guest favourite
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.
Apartment in Montepulciano

Dimora dell'Erbe - Rooftop Apartment

5.0 out of 5 average rating, 120 reviews
Guest favourite
A bright bedroom features large windows with green curtains that allow natural light to fill the space. A spacious bed is positioned beside a vintage-style dresser and a decorative chair. An artwork is displayed on the wall, contributing to the room's inviting ambiance.
Apartment in San Quirico d'Orcia

Comfortable Central Apartment Dimora delle Mura

4.93 out of 5 average rating, 124 reviews
Guest favourite
A sleeping area is presented with a double bed featuring white linens and a decorative blanket. Natural light filters through a sheer curtain over a window, illuminating the white walls and wooden ceiling beams. A bedside table is positioned beside the bed.
Apartment in San Quirico d'Orcia

Virgilio in Val d’Orcia

4.85 out of 5 average rating, 126 reviews
Guest favourite
The kitchen area is designed with modern cabinetry and features a dining table set for four. Large windows allow natural light to fill the space, while exposed wooden beams add character to the high ceiling. A glimpse of the outdoor scenery is visible through the glass doors.
Apartment in Monticchiello

Apartment Antica Toscana

4.92 out of 5 average rating, 147 reviews
Guest favourite
The exterior of the building showcases a three-story structure surrounded by greenery. Mature trees and flowering plants create a serene atmosphere, while a winding stone path leads through the garden. A charming fountain adds to the inviting outdoor space.
Apartment in Torrenieri

Lavender Apartment

4.87 out of 5 average rating, 149 reviews
Top Guest favourite
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

4.98 out of 5 average rating, 113 reviews
Superhost
The exterior of a rustic stone farmhouse is displayed under a clear blue sky. Lush greenery surrounds the structure, and colorful flower pots line the entrance steps. The building features arched windows and doors, while a staircase leads to the upper level.
Apartment in Castiglione d'Orcia

Casa al Poggio

4.81 out of 5 average rating, 27 reviews

Private apartment rentals

Superhost
Apartment in Montalcino

Wp Relais Argante Apartment

5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Scrofiano

Panoramic View New Apartment with Balcony and A/C

5.0 out of 5 average rating, 4 reviews
Top Guest favourite
Apartment in San Quirico d'Orcia

Apartment in Val d'Orcia

4.94 out of 5 average rating, 53 reviews
Guest favourite
A panoramic view of the Val di Chiana is framed by a brick archway. Rolling hills and a serene sky displaying soft hues of orange and pink capture the scenic beauty of the landscape, which stretches far into the distance.
Apartment in Montepulciano

La Terrazza dell'Eden, infinity view of Tuscany

4.93 out of 5 average rating, 72 reviews
Guest favourite
An outdoor dining area is set beneath a pergola adorned with grapevines, offering a scenic view of the surrounding hills and valleys. A table is arranged with dinnerware, surrounded by metal chairs, creating an inviting space for meals while enjoying the landscape.
Apartment in Montalcino

Podere Belsogno

4.93 out of 5 average rating, 88 reviews
Superhost
A rustic outdoor patio is framed by lush green vines, creating a natural canopy. A large table is surrounded by wooden and wrought-iron chairs, providing ample seating for guests. Sunlight gently filters through the arches of the adjacent building, enhancing the relaxed ambiance.
Apartment in San Giovanni d'Asso

Podere Ferranino #Brunelleschi Townhouse

4.95 out of 5 average rating, 22 reviews
Superhost
Apartment in Castiglione d'Orcia

Gemma Verde-tavoleto Apartment

4.62 out of 5 average rating, 26 reviews
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.
Apartment in Pienza

Artistic Pienza | Breathtaking Val d'Orcia View

4.66 out of 5 average rating, 231 reviews

Apartment rentals with a hot tub

Guest favourite
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.
Apartment in Monteroni d'Arbia

"Red Rose" apartment with view of Siena.

4.94 out of 5 average rating, 287 reviews
Guest favourite
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.
Apartment in Castelnuovo Berardenga

Villa di Geggiano - Perellino Suite

4.94 out of 5 average rating, 183 reviews
Top Guest favourite
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.
Apartment in Montepulciano

Charming House in Montepulciano

4.93 out of 5 average rating, 153 reviews
Guest favourite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena

Villa'Colombaiolo di Marciano', 28

4.9 out of 5 average rating, 146 reviews
Top Guest favourite
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

4.98 out of 5 average rating, 107 reviews
Guest favourite
An outdoor seating area is presented with a stone wall backdrop, featuring a round table surrounded by four white plastic chairs. A terracotta pot with flowers adds a touch of color. Natural light illuminates the space, highlighting the rustic stone and wooden beams above.
Apartment in Cortona

Agriturismo Pilari apt. Stalla

4.89 out of 5 average rating, 147 reviews
Guest favourite
A stone pathway leads to a rustic building adorned with vibrant yellow flowers, framed by wooden shutters. Surrounding greenery adds a lush atmosphere, while a small stone feature is visible to the side, enhancing the tranquil garden setting.
Apartment in Seggiano

Romantic farmhouse, garden apartment with panorama

4.86 out of 5 average rating, 80 reviews
Top Guest favourite
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

5.0 out of 5 average rating, 54 reviews

Destinations to explore