Apartment holiday rentals in Castiglion Fiorentino

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.

4.99 out of 5 average rating, 187 reviews

Cortona’s Rooftop Nest

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 accommodates 4 people. Fans in the bedrooms The apartment is located in the historic center right in front of the wonderful church of St. Francis and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can accommodate up to 4 people. Fans in the rooms.

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, 163 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

5.0 out of 5 average rating, 155 reviews

A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.

Apartment in Arezzo

Piazza Grande Boutique Apartment

Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.

The living area features a spacious sectional sofa, a modern television on a low cabinet, and a round dining table surrounded by four chairs. A map artwork adorns the wall, complemented by shelf plants, enhancing the open feel of the apartment.

4.92 out of 5 average rating, 105 reviews

Modern apartment in the heart of Tuscany

A few steps from Castiglion Fiorentino train station. Ideal for exploring not only this charming medieval city but also other beautiful Tuscan cities, such as Arezzo, Cortona and Siena. The apartment has 1 bathroom and 5 beds, ideal for families or groups of friends. There is also an additional sofa bed for extra guests. It also has a small loggia for relaxing. Its central location allows you to easily find services such as shops, restaurants and bars nearby.

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, 304 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.

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.

4.98 out of 5 average rating, 113 reviews

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

A spacious living area features a comfortable purple sofa and striped poufs, complemented by a classic wooden sideboard and elegant lamps. Warm colors adorn the walls, and a large artwork adds character. Natural light enters through multiple windows, enhancing the inviting ambiance.

4.97 out of 5 average rating, 187 reviews

CasaNella: central, bright, and with a view

Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.

4.96 out of 5 average rating, 419 reviews

Cortona Shabby Chic House - independent & balcony-

This is an apartment cared for by a Superhost who lives in Cortona every day. My place is located in the heart of the historic center just a few steps from the main squares and streets This cute apartment is recently renovated and sleeps up to 3 people. Independent apartment with single entrance all on one floor, with balcony. Thoughtfully furnished, equipped with all the comforts for total relaxation

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.

5.0 out of 5 average rating, 120 reviews

Dimora dell'Erbe - Rooftop Apartment

The apartment has two independent double bedrooms with private bathroom (Nepitella and Timo), a large bright kitchen with living room and finally exclusive access to the beautiful terraces that overlook the roofs of Montepulciano. The modern and functional kitchen offers an induction hob, dishwasher fridge and a service for 6 people. Independent air conditioning and heating and wi-fi.

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.

A small round table is set on a balcony, accompanied by two white chairs. A bottle of wine and two glasses are positioned on the table. The railing features decorative ironwork, framing a panoramic view over the terracotta rooftops and the valley below.

4.97 out of 5 average rating, 181 reviews

I Terrazzini apt.1

In one of the most beautiful old buildings of the hystorical center, completely refurbished very sunny and scenic: a balcony with a spectacular view over Cortona roofs,Valdichiana, Trasimeno Lake and mountains far away. Living,attic,dinig,kitchen,bathroom,two bedrooms. Just few steps down the street and you are in Ruga Piana or Signorelli Square "movida"

A serene outdoor space is framed by tall, leafy trees, creating a natural canopy. Within the gravel area, terracotta pots with greenery are visible, offering a sense of tranquility. The expansive view stretches across the hills and valleys of the surrounding landscape.

4.96 out of 5 average rating, 193 reviews

Casa Le Contesse

It's a small apartment, part of the farmhouse where I live. It's located on the ground floor, with independent access, on a hill amidst olive trees, one km from Cortona. Parking, private access, and use of the very scenic garden are available.

Popular amenities for Castiglion Fiorentino apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

Apartment in Monticchiello

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.

Casa Bonari - a paradise for the eyes

4.97 out of 5 average rating, 187 reviews

A rustic kitchen is highlighted by exposed wooden beams and a traditional stone fireplace. Blue tile decor complements white cabinetry and a spacious dining table surrounded by chairs. Natural light filters through a window, creating a warm and functional cooking space.

5.0 out of 5 average rating, 214 reviews

The source

A spacious bedroom features a warm terracotta ceiling with herringbone patterns. Natural light streams in through a window, illuminating the wooden furniture, including a wardrobe and a small table. Air conditioning is also visible, ensuring a comfortable environment.

4.96 out of 5 average rating, 25 reviews

Casa La Girandola – Journey through the medieval alleys

An aerial view of a stone farmhouse is presented, surrounded by lush greenery. A private garden features various seating arrangements, including loungers and a dining area under a sunshade. A pathway leads to the entrance, emphasizing the rustic charm of the setting.

5.0 out of 5 average rating, 39 reviews

Pendici 15, small apartment

Superhost

A cozy master bedroom features a spacious bed draped with soft linens. Wooden beams stretch across the ceiling, while bedside tables with lamps provide soft illumination. The warm tones of the walls create a serene environment, with a glimpse of the living area visible in the background.

4.7 out of 5 average rating, 27 reviews

Casa il Cassero, rustic-style apartment free WI-FI

A living area features a comfortable gray sofa accompanied by a bright decorative cushion. Light wood flooring complements the simple dining table and chairs. The walls are adorned with framed artwork and mirrors, providing a welcoming ambience.

4.93 out of 5 average rating, 14 reviews

Casa Sonia

5.0 out of 5 average rating, 14 reviews

Casa il Giardino

The lounge room features a charming design with pale pink walls and a richly decorated ceiling. An ornate chandelier hangs above, illuminating an antique wooden cabinet and a comfortable seating arrangement with light-colored sofas. A round, decorative coffee table sits at the center, adding functionality.

4.9 out of 5 average rating, 62 reviews

Casa Nobile

Private apartment rentals

4.98 out of 5 average rating, 53 reviews

Luna Apartment

An aerial view captures a historic farmhouse set amidst expansive olive groves. Lush greenery surrounds the property, with neatly arranged trees and a sparkling swimming pool visible. The outdoor space features a well-maintained garden, ideal for relaxation and leisure.

5.0 out of 5 average rating, 23 reviews

Casale La Cedrina (Il Melograno)

Apartment in San Leo Bastia

An outdoor space is featured, showcasing a stone structure with a door leading inside. A rustic table is set with glasses and plates, surrounded by vibrant yellow flowers and green shrubs, creating a serene environment for dining.

Hamlet San Biagio a Colle – House of Venus

5.0 out of 5 average rating, 41 reviews

Apartment in Marciano della Chiana

Frutteti Apartment 4 + 2 + 2 + 2 | up to 135 sqm

4.95 out of 5 average rating, 58 reviews

4.93 out of 5 average rating, 40 reviews

Apartment in Arezzo

The Little Court

4.9 out of 5 average rating, 42 reviews

An outdoor lounge area is shaded by a lush pergola, offering expansive views of the surrounding countryside. Comfortable seating surrounds a modern round table, while a potted plant adds a touch of greenery, creating a serene spot for relaxation.

Apartment in Lucignano

Palazzo Trapani Luxury Residence

4.89 out of 5 average rating, 70 reviews

A spacious living area features large windows allowing natural light to fill the room. The space includes a comfortable seating arrangement, a dining table set with serving pieces, and distinctive ceiling structures. A warm wooden floor complements the modern decor and exposed brick wall.

Apartment in Arezzo

modus apartments

The image captures a quiet evening view of a historic town, with softly lit buildings nestled among lush greenery. A faint outline of a church is visible against the darkening sky, while the surrounding hills add a sense of depth to the scene.

4.92 out of 5 average rating, 25 reviews

Bel Tramonto, historic center with private garden

Apartment rentals with a hot tub

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.

"Red Rose" apartment with view of Siena.

4.94 out of 5 average rating, 287 reviews

The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.

4.99 out of 5 average rating, 168 reviews

Villa di Geggiano – Alfieri Suite

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.

4.89 out of 5 average rating, 147 reviews

Agriturismo Pilari apt. Stalla

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

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.

4.9 out of 5 average rating, 146 reviews

Villa'Colombaiolo di Marciano', 28

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.