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, 189 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, 165 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

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.

5.0 out of 5 average rating, 155 reviews

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.

Apartment in Castiglion Fiorentino

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.

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.

4.93 out of 5 average rating, 109 reviews

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, 310 reviews

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.

4.97 out of 5 average rating, 116 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

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.

4.98 out of 5 average rating, 414 reviews

Apartment in Sinalunga

Resort Panoramic view - Free parking

New apartment, powerful Wi-Fi, SMART TV, private bathroom, air conditioning, private kitchen, laundry room , free private parking. Free dessert buffet. Breathtaking panoramic view . Between the Crete Senesi and the Val D'Orcia, 800 meters from the center of the village, with restaurants, bars and supermarkets. Strategic place for visiting the main towns in Tuscany : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

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, 423 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

A spacious bed with an intricately designed headboard features soft, neutral bedding accented with decorative pillows. Two bedside lamps illuminate the space, each adorned with a delicate shade. A small tray with tea cups and a book is positioned on the bed, adding a touch of comfort.

4.91 out of 5 average rating, 115 reviews

Scacciapensieri Guest House in Arezzo's historic center

Description: Scacciapensieri Guest House is a characteristic three-story townhouse located a stone's throw from Piazza Grande, the heart of Arezzo's historic center. An optimal location for visiting the city and its treasures, very close to the station, which can be easily reached in less than a 10-minute walk.

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.

4.91 out of 5 average rating, 239 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.

Superhost

The image features a spacious living area with an elegant sofa adorned with greenery-patterned cushions. An archway reveals a cozy sleeping area with a well-placed bed, highlighted by warm lighting and soft decor. The wooden ceiling beams add a touch of character to the room.

Apartment in Castiglion Fiorentino

❤️ of Castiglion Fiorentino, Studio with Courtyard

• Walk Score 85 (‘Very Walkable’) • Courtyard • 20min walk to train station • Extremely safe neighborhood • Fully equipped kitchen • Washer on-site • Ideal for visitors of Santa Chiara Study Center

4.84 out of 5 average rating, 110 reviews

A charming two-story villa is situated on a grassy expanse, showcasing a traditional Tuscan design with stone and plaster elements. A covered porch is present, alongside a patio area furnished with a round table and chairs. Flower pots and greenery enhance the outdoor setting.

4.88 out of 5 average rating, 248 reviews

" Le Tre Civette" Country House

Single house 4 miles away from Arezzo historic center: master bedroom with private bathroom and Tuscan style kitchen. Separate entrance, parking and front yard available for our guests.

Popular amenities for Castiglion Fiorentino apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, 182 reviews

I Terrazzini apt.1

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, 195 reviews

Casa Le Contesse

4.89 out of 5 average rating, 270 reviews

A view showcases the rooftops of Pienza, featuring a blend of rustic tiles and historic bell towers. The image captures the warm hues of a sunset sky, enhancing the architectural details of the clock tower and surrounding structures.

Apartment in Pienza

Renaissance Apartment

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 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, 188 reviews

CasaNella: central, bright and with a view

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, 124 reviews

Dimora dell'Erbe - Rooftop Apartment

4.99 out of 5 average rating, 118 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

Apartment in Castiglion Fiorentino

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.

Pendici 15, small apartment

5.0 out of 5 average rating, 41 reviews

Private apartment rentals

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, 63 reviews

Casa Nobile

4.98 out of 5 average rating, 52 reviews

Ca' delle Acquarelli

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.

4.89 out of 5 average rating, 71 reviews

modus apartments

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.

Tuscany jem: The Chianti Farmer's House

4.98 out of 5 average rating, 87 reviews

4.93 out of 5 average rating, 42 reviews

The Little Court

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, 26 reviews

Casale La Cedrina (Il Melograno)

Apartment in Fratta-Santa Caterina

The spacious living area features exposed wooden beams and brick arches, with a warm-toned terracotta floor. A wooden table and chairs are visible, alongside a cozy seating arrangement in yellow fabric. Natural light enters through large windows, enhancing the inviting ambiance.

Charming apartment with small gardens, pool access

4.87 out of 5 average rating, 30 reviews

4.85 out of 5 average rating, 26 reviews

Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

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, 288 reviews

4.99 out of 5 average rating, 168 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.

Apartment in Siena

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

4.84 out of 5 average rating, 107 reviews

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

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