Apartment holiday rentals in Castellina in Chianti

4.98 out of 5 average rating, 343 reviews

A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.

Apartment in Poggibonsi

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility in the heart of the Chianti countryside. The apartment is halfway between Florence and Siena, and is in a strategic position for quickly reaching Florence, Siena, San Gimignano, Volterra, as well as the wonderful Chianti hills. The apartment has ample private parking, two bedrooms, an equipped kitchen, a private bathroom, a private garden, a barbecue, and a wonderful view of the Chianti hills.

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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.

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.

ValueLocationBiking

4.94 out of 5 average rating, 188 reviews

Apartment in Barberino Val d'Elsa

A restored stone mill stands surrounded by trees in a tranquil setting. The building features multi-level architecture with red window accents. A gravel pathway leads to the structure, while a vibrant green lawn and rustic stone borders enhance the natural landscape.

Apartment in Chianti at Mulino dell'Argenna

The apartment of the Roses is located inside the Mulino dell'Argenna guest house. The property was completely restored in 2015. It is an ancient stone mill dating back to 1400, built along the course of the Borro dell'Argenna. The Mill is an enchanting place, surrounded by the greenery of the forest, with a beautiful one-hectare park and a large swimming pool. An ideal place to spend your days in Tuscany in maximum privacy, in full contact with nature.

ValueFamilyAmenities

4.99 out of 5 average rating, 154 reviews

A heated pool is surrounded by lush greenery, offering scenic views of the rolling hills. The pool's clear water reflects the sky, while a fenced area provides safety. Flowering plants are positioned along the edges, enhancing the natural beauty of the setting.

4.94 out of 5 average rating, 210 reviews

Visit Chianti, Siena, Florence, S.Gimignano

Apartment into Borgo Sicelle Residence, in Castellina inChianti area (between Florence, Siena, S.Gimignano). Two people. It has a kitchen, a double bedroom, a bathroom with shower. It's on the first floor. Outside there are shared tables. Pool heated up to25 degrees in Spring and Autumn In front of the property there is a restaurant (Osteria Uscio e Bottega), closed on Wednesday. There is no public transport to reach the property Car is required

LocationValueAir conditioning

4.85 out of 5 average rating, 354 reviews

La dolce vita in Chianti. Swimming pool and relaxation

Apartment nestled in the Chianti Classico hills, in the village of Tregole, 5 km from Castellina in Chianti. Private apartment in a typical Tuscan farmhouse. Suitable for those who want to spend a vacation immersed in nature in complete relaxation and silence. Ideal starting point for visiting the most important places in Tuscany. The apartment is equipped with all comforts. Linen and final cleaning are included in the price. Children are welcome

ValueFamilyCondition

4.92 out of 5 average rating, 391 reviews

An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.

Apartment in Gavignano

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.

ValueFamilyTV

4.97 out of 5 average rating, 117 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.

FamilyLocationQuiet

Apartment in Badia a Passignano

A large shared pool is set against a backdrop of rolling hills and open skies. Several lounge chairs are arranged around the pool, offering a space for relaxation. The clear turquoise water reflects the surrounding landscape and clouds above.

Chianti, Country house with pool

Peace and relax in the heart of Chianti between Florence and Siena, close to Badia a Passignano (4 km dirt road not too much easy if you drive a sportive car) . In an old farmhouse complex, the apartment "Sangiovese" was recently restored by retrieving the characteristics of the Tuscan rural tradition. Large shared pool (01/05 - 30/09) .

ValueFamilyLaundry

4.92 out of 5 average rating, 141 reviews

Apartment in Monteriggioni

An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.

Comfort Apartment in the Chianti Vineyards

Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, a kitchenette, a double bedroom, a private bathroom with a shower, air conditioning.

ValueLocationBiking

4.93 out of 5 average rating, 455 reviews

4.98 out of 5 average rating, 130 reviews

A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.

Apartment in San Gusmè

Casa Guardiavigna | Chianti Hills Vineyard Retreat

The Casa Guardiavigna apartment offers the opportunity to enjoy a unique and extraordinary experience, full of emotions and happiness. Located a stone's throw from the small medieval village of San Gusme' and surrounded by beautiful vineyards, woods and flowery meadows. Free indoor parking with an automatic gate.

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A clear swimming pool reflects the sky, surrounded by lounge chairs and sun umbrellas, set against the backdrop of a rustic stone building. Lush greenery completes the serene outdoor space.

4.91 out of 5 average rating, 141 reviews

Casa Tatini your house in Chianti

Casa Tatini is in the heart of Chianti just 500 meters from Castellina in Chianti in the middle of the vines and nature, to relax in the greenery. The house, equipped with swimming pool, consists of a double bedroom, living room with kitchen and private bathroom.

ValueLocationComfort

4.98 out of 5 average rating, 282 reviews

A scenic view of the surrounding countryside presents rolling hills and lush vineyards. Colorful flowers and greenery frame the pathway leading towards the entrance, under a partly cloudy sky that allows for ample sunlight.

Apartment in Poggibonsi

OLIVE TREE APARTMENT - CHIANTI

Lovely apartment in a magnificent hilly location in Chianti halfway between Florence and Siena from which you can reach and visit the most beautiful cities of art and villages in Tuscany.

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Popular amenities for Castellina in Chianti apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.98 out of 5 average rating, 138 reviews

An aerial view captures the medieval village of Certaldo, featuring terracotta rooftops and winding streets. The lush greenery surrounding the village adds a natural touch, while historic buildings stand prominently, showcasing varied architectural styles. The placement of the highlighted property is evident within the quaint atmosphere.

Apartment in Certaldo

House in a medieval tower with a view in Certaldo

FamilyLocationWalkability

A modern dining area features a large wooden table surrounded by sleek black chairs, with expansive glass walls offering views of the surrounding hills and city. The space is well-lit by hanging pendant lights, creating a bright and inviting environment.

4.96 out of 5 average rating, 399 reviews

Rooftop with Breathtaking Views. Short Walk to The Duomo.

LocationFamilyGetting around

4.86 out of 5 average rating, 275 reviews

A serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.

Apartment in La Presura

Countryhouse 9 kms to Florence-3+2,free park, wine

ValueLocationBiking

A well-equipped kitchen features wooden cabinetry and exposed beams. Copper pots are hung on a rack, complementing tile countertops. A doorway opens to outdoor views, allowing natural light to illuminate the space.

4.87 out of 5 average rating, 79 reviews

Apartment T4

LocationFamilyNearby

A scenic balcony features a small table, adorned with bottles of wine and a dish of fresh green grapes. The view showcases rolling hills and vineyards under a clear blue sky, emphasizing the tranquil surroundings.

4.97 out of 5 average rating, 30 reviews

Edera

ValueFamilyView

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

LocationFamilyCleanliness

4.98 out of 5 average rating, 89 reviews

4.95 out of 5 average rating, 58 reviews

Casa Mirella in Chianti

ValueLocationAccuracy

4.89 out of 5 average rating, 35 reviews

The Farmhouse in Chianti-IlVillinoFarmhouse

FamilyLocationShared spaces

Private apartment rentals

Apartment in Barberino Val d'Elsa

Lorenzo Charme in Chianti

LocationFamilyHospitality

5.0 out of 5 average rating, 28 reviews

4.82 out of 5 average rating, 51 reviews

Casa Bruna – Cipresseta del Chianti

FamilyLocationHospitality

4.93 out of 5 average rating, 60 reviews

Apartment in Cavriglia

Apartment Comfort | Quiet Escape in Tuscany

LocationValueIndoor spaces

Apartment in San Casciano In Val di Pesa

A serene outdoor area features a spacious pool surrounded by neatly trimmed green lawns and several umbrella-covered seating areas. Lush cypress trees and rolling hills form the backdrop, while distant mountains are visible under a clear sky.

Luna Suite at Villa Santa Lucia Nuova

FamilyLocationNearby

5.0 out of 5 average rating, 29 reviews

4.94 out of 5 average rating, 49 reviews

A well-equipped kitchen features a large wooden dining table surrounded by white chairs. Decorative tiles add a touch of character to the walls, with ample counter space and vintage kitchenware displayed. Natural light enters through charming windows, enhancing the functional layout.

Apartment in Poggibonsi

Large Tuscan Chianti Tower suite Apartment

FamilyLocationQuiet

4.85 out of 5 average rating, 26 reviews

Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

ValueFamilyHospitality

5.0 out of 5 average rating, 4 reviews

Apartment in Bossi

Villino Ersilia Music, the charm of Chianti

LocationFamilyPool

Apartment in San Gimignano

Private Courtyard | 3BR/3BA | Garage

LocationFamilyBiking

5.0 out of 5 average rating, 15 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.

ValueFamilySleep quality

4.94 out of 5 average rating, 288 reviews

4.91 out of 5 average rating, 149 reviews

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

LocationValueIndoor spaces

4.89 out of 5 average rating, 102 reviews

Healthy Home | Duomo • Jacuzzi & Green Oasis

ValueFamilyLayout

An expansive terrace features a large table surrounded by black chairs, offering a panoramic view of the city. Bright green lounge chairs provide a spot for relaxation. Decorative tiles enhance the visual appeal against a backdrop of historic architecture and blue skies.

4.83 out of 5 average rating, 166 reviews

At the top faboulous terrace Florence

LocationFamilyView

A living area is presented with a light-colored sofa and a glass coffee table on a patterned rug. Walls are adorned with framed artwork, and a large television is positioned in a wooden cabinet. Double doors lead to an outdoor space, enhancing natural light.

4.99 out of 5 average rating, 102 reviews

Fully renovated exclusive apartment in Villa

FamilyLocationBackyard

A serene garden scene features a table set with a floral-patterned teapot and matching cups. Lush greenery surrounds the area, with terracotta pots and vibrant flowers enhancing the natural setting. The space is bathed in soft sunlight, providing a tranquil outdoor retreat.

4.89 out of 5 average rating, 371 reviews

Apartment with garden and parking

ValueLocationBackyard

4.8 out of 5 average rating, 147 reviews

Apartment in San Marco

Duomo FillYourHomeWithLove Design Apartment

LocationValueHeating