Apartment holiday rentals in Castiglion Fiorentino

A spacious bedroom features a king size bed adorned with light bedding, complemented by decorative pillows. A chair is positioned near the window, which opens to a small private terrace with greenery visible. Iroko wooden parquet flooring adds a warm touch.

4.99 out of 5 average rating, 184 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.

FamilyValueAir conditioning

5.0 out of 5 average rating, 153 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.

ValueFamilyAir conditioning

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, 165 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.

FamilyValueAmenities

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, 104 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.

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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.

FamilyValueBathroom

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, 186 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.

ValueFamilyBreakfast

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, 416 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

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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.

5.0 out of 5 average rating, 102 reviews

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.

LocationCheck-inAccuracy

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.

ValueFamilyAccuracy

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, 179 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"

ValueFamilyView

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, 191 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.

ValueLocationPool

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.

4.83 out of 5 average rating, 109 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

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Popular amenities for Castiglion Fiorentino apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, 284 reviews

"Red Rose" apartment with view of Siena.

LocationFamilyTV

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, 232 reviews

Tuscany on the terrace, downtown Montepulciano

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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.

4.97 out of 5 average rating, 411 reviews

Romantic Tower's dating 1200

ValueLocationDecor

A spacious terrace is shown, featuring comfortable seating arrangements, including lounge chairs and a small dining table. The area is partially shaded by awnings, with a view of the surrounding landscape. A table is set with fresh strawberries and beverages, inviting relaxation.

5.0 out of 5 average rating, 101 reviews

Terrace on the walls of Siena - Casa Laura

FamilyLocationAccuracy

A spacious living area is showcased with large windows offering panoramic views of the surrounding hills. A dining table sits in the center, accompanied by chairs, while a comfortable seating arrangement is positioned nearby. Natural light fills the space, highlighting the earthy tones and wood accents.

4.97 out of 5 average rating, 443 reviews

A view from the top, Montepulciano

LocationValueLong stay

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.

FamilyValueHiking

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

ValueFamilyComfort

Apartment in Villa A Sesta

A serene garden area is visible, featuring two wooden lounge chairs positioned on lush green grass. Surrounding plants and flowers add a touch of color. The stone house in the background features multiple windows, framed by greenery and terracotta pots.

4.94 out of 5 average rating, 243 reviews

At Paola's in Chianti

FamilyLocationWi-Fi

Private apartment rentals

Apartment in Passignano sul Trasimeno

5.0 out of 5 average rating, 54 reviews

Sunset on the Lake – Passignano Centro Lake view

LocationAir conditioningBathroom

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

LocationHospitalityNearby

4.89 out of 5 average rating, 19 reviews

Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

LocationValueAmenities

5.0 out of 5 average rating, 39 reviews

Casa AlMa: air conditioning and private terrace

LocationWalkabilityIndoor spaces

4.94 out of 5 average rating, 83 reviews

Apartment in Scrofiano

Bright Tuscany Apartment with view, balcony, A/C

LocationFamilyHospitality

5.0 out of 5 average rating, 57 reviews

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.

Apartment in Pienza

Live Like a Local & Private Concierge Service

ValueLocationCheckout

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.

4.69 out of 5 average rating, 26 reviews

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

LocationFamilyKitchen

4.96 out of 5 average rating, 94 reviews

An outdoor dining area features a large table set for four under a spacious umbrella. Two lounge chairs are positioned nearby, surrounded by stone pavers and potted plants. The charming facade of the villa can be seen in the background, enhancing the peaceful ambiance.

Apartment in Arezzo

Villa Medici Donnini Deluxe Apartment

FamilyLocationHospitality

Apartment rentals with a hot tub

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, 112 reviews

Luxury frescoed apartment in the historical center

FamilyLocationGetting around

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, 144 reviews

Agriturismo Pilari apt. Stalla

FamilyLocationCheckout

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.

4.91 out of 5 average rating, 143 reviews

Villa'Colombaiolo di Marciano', 28

FamilyLocationShared spaces

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

ValueFamilyBathroom

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.

4.98 out of 5 average rating, 107 reviews

Domus Nannini - L'Arco di Matteotti Spa

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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

LocationValueWalkability

4.93 out of 5 average rating, 14 reviews

A cozy sleeping area features an elegant bed with a soft white comforter, complemented by exposed stone walls that add texture to the room. A staircase leads to a loft area, while a living space is visible with a green sofa and patterned rug, providing additional comfort.

Apartment in Lucignano

Design Suite Lucignano | Four

FamilyLocationParking

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.