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.

LocationValueBreakfast

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

ValueLocationLong stay

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.

FamilyLocationCleanliness

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.

4.93 out of 5 average rating, 109 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.

FamilyLocationComfort

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. Complimentary 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 .

ValueFamilyWi-Fi

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.

LocationFamilyCheckout

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

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.

LocationValueDecor

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

ValueLocationHospitality

Apartment in Monticchiello

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.

Casa Tòrta - 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.

LocationSolo travelCheck-in

5.0 out of 5 average rating, 107 reviews

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, 196 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.

LocationValueSleep quality

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.

4.84 out of 5 average rating, 110 reviews

❤️ 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

FamilyValueTV

4.88 out of 5 average rating, 248 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.

Apartment in Arezzo

" 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.

FamilyLocationShared spaces

Popular amenities for Castiglion Fiorentino apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, downtown Montepulciano.

LocationFamilyAmenities

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

ValueFamilyOutdoor spaces

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

FamilyLocationAmenities

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

LocationValueKitchen

Apartment in Monticchiello

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.

Romantic Tower's dating 1200

ValueLocationAir conditioning

4.97 out of 5 average rating, 414 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, 217 reviews

The source

FamilyValueGetting around

4.91 out of 5 average rating, 115 reviews

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.

Apartment in Arezzo

Scacciapensieri Guest House in Arezzo's historic center

FamilyLocationParking

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

LocationFamilyHospitality

Private apartment rentals

5.0 out of 5 average rating, 14 reviews

Casa il Giardino

LocationFamilyLaundry

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, 15 reviews

Casa Sonia

LocationParkingAmenities

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

LocationFamilyCheck-in

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

FamilyLocationQuiet

4.87 out of 5 average rating, 30 reviews

4.98 out of 5 average rating, 52 reviews

Ca' delle Acquarelli

FamilyLocationParking

4.98 out of 5 average rating, 49 reviews

Casa AlMa: air conditioning and private terrace

LocationSleep qualityKitchen

4.85 out of 5 average rating, 26 reviews

Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

FamilyLocationGetting around

Apartment in Passignano sul Trasimeno

Sunset on the Lake – Passignano Centro Lake view

LocationComfortView

5.0 out of 5 average rating, 59 reviews

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.

FamilyValueWi-Fi

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

ValueFamilyParking

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

FamilyValueWi-Fi

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

FamilyLocationAccuracy

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

LocationValueKitchen

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

LocationValueLong stay

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

Apartment with garden in the heart of Tuscany

ValueFamilyWi-Fi

4.88 out of 5 average rating, 105 reviews

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.