Pet-friendly holiday rentals in Castellina in Chianti

A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.

4.94 out of 5 average rating, 235 reviews

The Farmhouse Cottage

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

4.99 out of 5 average rating, 141 reviews

An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.

Cottage

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

4.95 out of 5 average rating, 265 reviews

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

4.97 out of 5 average rating, 319 reviews

An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.

Apartment

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and Wi-Fi A strategic location for visiting Tuscany and Umbria.

A tranquil outdoor pool is surrounded by well-maintained gardens and olive trees. Sun loungers are positioned along the poolside, providing space for relaxation. The stone-clad building in the background complements the landscape, contributing to the serene environment.

4.92 out of 5 average rating, 159 reviews

Country house 9 km to Florence-2+1g,free parking

We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.

4.91 out of 5 average rating, 235 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.

4.96 out of 5 average rating, 312 reviews

Casa Al Poggio & Chianti view

Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

4.88 out of 5 average rating, 118 reviews

Castle

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Superhost

A warm and inviting fireplace is surrounded by various decorative elements, including potted plants and wall art. Baskets filled with logs are neatly arranged, enhancing the cozy ambiance. Natural light enters through nearby windows, creating a bright and comfortable space.

4.89 out of 5 average rating, 173 reviews

Nada Home

My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

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, 127 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.

A serene pool area is featured, surrounded by well-maintained greenery. Several lounge chairs are positioned along the pool's edge, inviting relaxation. The sky is clear and blue, complementing the tranquil setting of the property.

4.94 out of 5 average rating, 164 reviews

Podere Guidi

Apartment in a panoramic villa between Florence and Siena, in the heart of Chianti, in a charming village. Pool open from May until the end of September. From 2026, the pool will be open from 9 am to 1 pm with exclusive use for guests during this time.

4.92 out of 5 average rating, 111 reviews

A terrace is showcased, featuring a wooden table accompanied by white chairs. The scene includes expansive views of rolling hills and vineyards, framed by tall cypress trees. The sky reveals warm sunset hues, creating a serene atmosphere.

Holiday home

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Popular amenities for Castellina in Chianti pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An outdoor area features a quaint seating arrangement with a small table and four chairs, nestled under the shade of a rustic covered porch. Surrounding planters hold vibrant flowers, and a brick well adds charm to the lush green lawn.

4.95 out of 5 average rating, 488 reviews

Casa del Giardino

Well-maintained gardens feature a lush lawn surrounded by mature trees, providing shade. An old stone building is visible in the background, characterized by arched windows and a terracotta roof. A shaded outdoor seating area, under a rustic wooden eave, adds to the inviting exterior.

4.97 out of 5 average rating, 116 reviews

Torretta Apartment

A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.

4.92 out of 5 average rating, 143 reviews

Private villa/swimming pool in Tuscany

The exterior view features a rustic stone house surrounded by greenery, including trees and flowering plants. Sun loungers are positioned on the lawn, creating a space for relaxation. A spacious terrace extends from the house, providing access to the inviting garden area.

4.99 out of 5 average rating, 172 reviews

Tuscany .Countryhouse on the Florence's hills

A decorative wall shelf is embedded in a stone wall, featuring a small potted plant and a light fixture above. Below the plant, a set of wine glasses is arranged on a glass surface, adding a touch of elegance to the rustic backdrop.

4.96 out of 5 average rating, 265 reviews

House for the Coast

A charming stone exterior reveals a rustic villa surrounded by greenery. The entrance features a wooden door and terracotta roof tiles. Potted plants add color, while seating areas are positioned on a patio, inviting relaxation in the scenic surroundings under a clear blue sky.

4.92 out of 5 average rating, 157 reviews

Casa Dante

A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.

4.94 out of 5 average rating, 109 reviews

Casa Luigi Suite with exclusive pool

A spacious bed is dressed in soft white linens, complemented by decorative pillows. Two bedside tables with lamps stand on either side, providing gentle illumination. The walls feature warm tones and framed artwork, contributing to a calming and serene atmosphere.

4.85 out of 5 average rating, 221 reviews

Gaiole in Chianti Poggio Casabianca

Pet-friendly home rentals with a pool

The spacious living area features rustic wooden beams and terracotta tiled flooring. A well-equipped kitchen is visible, accompanied by a dining table. Comfortable seating is arranged around a central point, while large windows allow natural light to fill the room.

4.86 out of 5 average rating, 117 reviews

The Porchereccia delle Bartaline

A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.

4.98 out of 5 average rating, 108 reviews

San Giovanni in Poggio, villa Meriggio 95mq

A tranquil scene of a swimming pool reflects the blue sky and surrounding greenery. Lush trees and rustic buildings are visible in the background, providing a serene backdrop. Wooden deck chairs line the poolside, inviting relaxation in a natural setting.

4.98 out of 5 average rating, 222 reviews

La Villa farm stay - L'Olivo, Pool & Hot Tub

4.86 out of 5 average rating, 132 reviews

A serene garden setting features a well-maintained lawn with loungers under shaded umbrellas. In the background, a rustic building is partially visible among tall trees, contributing to a tranquil atmosphere. A sign indicates the availability of complimentary wine tasting experiences.

Apartment

Fattoria Lornano Winery- villa ''Trebbiano''

An aerial view of a beautiful countryside property is shown, featuring a stone farmhouse surrounded by lush greenery, gardens, and vineyards. A shared swimming pool is visible, along with outdoor seating areas and well-maintained landscaping that highlights the tranquil rural setting.

4.91 out of 5 average rating, 323 reviews

holidays with swimming pool in Tuscany

Superhost

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.

4.83 out of 5 average rating, 59 reviews

Apartment T4

5 out of 5 average rating, 6 reviews

Casanovina

A dining table is set under the shade of lush trees, featuring a bottle of wine and glasses. The surrounding garden is filled with tall cypress trees and vibrant greenery, creating a serene atmosphere for outdoor dining.

4.78 out of 5 average rating, 163 reviews

Sperone: two floors apartment with pool

Private, pet-friendly home rentals

4.88 out of 5 average rating, 311 reviews

A spacious living area features large arched windows offering panoramic views of the Tuscan hills. A black leather sofa and a rocking chair are arranged around a decorative coffee table, with a subtle light from a chandelier above. A fireplace adds warmth to the serene space.

Townhouse

Florence Country Side: Giogoli a place to be!

An inviting outdoor dining area is framed by a large brick archway, showcasing a panoramic view of the Tuscan countryside. A wooden table is set with white dishes, a coffee pot, and a book, complemented by fresh flowers in a vase and decorative elements.

4.98 out of 5 average rating, 42 reviews

The Arches of Corsanello | Apt "Siena" x 3

An antique wrought iron gazebo features a round stone table set with wine glasses, a selection of wines, and a cheese platter. Colorful flowers are placed around the table, with green gardens and an ancient stone building visible in the background.

5 out of 5 average rating, 17 reviews

beautiful farmhouse in the Chianti panoramic garden

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.

5 out of 5 average rating, 15 reviews

Edera

The open-plan living area features wooden beams across the ceiling. Natural light filters through multiple windows, illuminating the cozy seating and dining areas. A rustic stone wall adds character, while a wooden table and light-colored chairs provide a functional dining space.

4.96 out of 5 average rating, 239 reviews

Casa Irene

Superhost

The expansive view of rolling hills is captured under a dynamic sky filled with scattered clouds. The lush greenery contrasts with the golden fields, creating a serene landscape. In the foreground, the garden area is surrounded by rustic pathways and trees, enhancing the natural setting.

4.89 out of 5 average rating, 334 reviews

Le Splandole Farm – Crete Senesi

5 out of 5 average rating, 33 reviews

To be happy in Tuscany with comfort & view!

The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.