Pet-friendly holiday rentals in Castellina in Chianti

4.97 out of 5 average rating, 194 reviews

An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.

Home in Simignano

Casa al Gianni - The Simignano Barn

Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

WalkabilityOutdoor spacesCondition

Villa 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.

Manor House - IlVillinoFarmhouse

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

WalkabilityOutdoor spacesCheck-in

4.93 out of 5 average rating, 254 reviews

4.88 out of 5 average rating, 338 reviews

Townhouse in Scandicci

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Outdoor spacesPetsKitchen

4.99 out of 5 average rating, 155 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 in Geggiano

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.

PetsOutdoor spacesCondition

Home in Castelnuovo Berardenga

A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.

The Chianti window

A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Outdoor spacesPetsLong stay

4.9 out of 5 average rating, 133 reviews

4.92 out of 5 average rating, 386 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

Cosy apartment for 4 people, furnished in Tuscan style with exposed beams, nestled among the rolling hills of the Tuscan countryside. Guests have access to a fully equipped garden, free Wi-Fi, a shared swimming pool with facilities, a wood-fired oven and barbecue, and a washing machine. The apartment is housed in a charming 19th-century stone farmhouse that has recently been renovated in the Tuscan style and divided into three comfortable apartments.

Outdoor spacesPetsKitchen

Superhost

4.87 out of 5 average rating, 215 reviews

Nada Home

3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

Outdoor spacesWalkabilityPool

Cottage in Castellina in Chianti

Leccio Cottage - Masseto In Chianti

MASSETO IN CHIANTI, located in La Piazza, between Panzano and Castellina in Chianti, is a private village where you can relax in the garden and near the pool, play sports, or pivot to visit many surrounding Renaissance towns like Firenze, Siena, San Giminiano, Arezzo, Volterra. Kids can move carefree in the village. We offer four indipendent ancient cottages : Quinto (2 beds), Vittoria (4 beds), Cappero (4 beds), Leccio (6 beds).

PetsWalkabilityFamily

4.96 out of 5 average rating, 102 reviews

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, 330 reviews

Casa Al Poggio in Chianti Shire

Casa al Poggio is a 145 sqm Tuscan country house in the heart of Chianti. The ground floor features a large living area with a kitchen and fireplace. Upstairs are 2 double bedrooms and an open room with a versatile sofa bed (set up as a double or 2 singles). A relaxing bathroom offers a shower, bathtub, and Chianti views. Outside, a terrace in the gravel garden awaits for your evenings. Perfect for experiencing authentic Tuscany!

Outdoor spacesPetsSleep quality

4.96 out of 5 average rating, 131 reviews

The garden features a shaded dining area with a large umbrella and a wooden table set with chairs. A brick barbecue stands nearby, surrounded by greenery and well-maintained grass. The entrance to the house is visible through elegant wrought iron doors.

Cottage in La Piazza

Casa La Misura in the heart of Chianti

La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

PetsOutdoor spacesCondition

Castle in Barberino Tavarnelle

An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.

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.

WalkabilityPetsValue

4.88 out of 5 average rating, 126 reviews

Apartment in Castellina in Chianti

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.

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.

PetsWalkabilityBathroom

4.91 out of 5 average rating, 140 reviews

Popular amenities for Castellina in Chianti pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 103 reviews

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.

Home in Greve in Chianti

Casa Giulia di Sopra Farmhouse

Outdoor spacesWalkabilityCheckout

4.93 out of 5 average rating, 152 reviews

Home in Il Poggetto

The Loggia

WalkabilityOutdoor spacesLocation

4.91 out of 5 average rating, 124 reviews

SuiteLouise.pool, Hot Tub,homeGym & private Garden

WalkabilityOutdoor spacesPool

4.95 out of 5 average rating, 200 reviews

A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.

Home in Pievescola

Borgo Ripostena – No. 8 Casa Vecchia

PetsOutdoor spacesCleanliness

4.83 out of 5 average rating, 157 reviews

Home in Monteriggioni

Next to castle of Villa-Siena. heart Francigena

PetsWalkabilityDecor

4.96 out of 5 average rating, 242 reviews

A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.

Home in Greve in Chianti

Love in Chianti

WalkabilityPetsAccess

4.98 out of 5 average rating, 218 reviews

A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.

Home in Siena

Secret Garden Siena

PetsWalkabilityCheckout

Home in Terranuova Bracciolini

Villa Lolù with private heated swimming-pool

PetsWalkabilityBarbecue

4.97 out of 5 average rating, 159 reviews

Pet-friendly home rentals with a pool

Superhost

The exterior of a charming stone villa is showcased, with a refreshing swimming pool in the foreground. Lush green grass surrounds the pool area, and a shaded gazebo with seating is positioned nearby. Rolling hills and a clear blue sky form a picturesque backdrop.

Villa in Greve in Chianti

Villa La Doccia, Greve in Chianti

Outdoor spacesPetsComfort

4.85 out of 5 average rating, 179 reviews

4.95 out of 5 average rating, 219 reviews

A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.

Tower in Fiesole

A Big Dream in a Little Tower.

Outdoor spacesWalkabilityGetting around

4.89 out of 5 average rating, 307 reviews

Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

WalkabilityOutdoor spacesCleanliness

Farm stay in Badia a Passignano

A spacious swimming pool is surrounded by a sun terrace featuring red and cream sun loungers. The lush green landscape of the Chianti hills is visible in the background, under a sky adorned with soft, white clouds.

A barn in Chianti

Outdoor spacesWalkabilityNearby

4.8 out of 5 average rating, 252 reviews

Holiday home in Panzano in Chianti

The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.

Fienile Santa Teresa

Outdoor spacesWalkabilityPool

4.98 out of 5 average rating, 174 reviews

Farm stay in Monte San Savino

A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

WalkabilityOutdoor spacesValue

4.99 out of 5 average rating, 113 reviews

Farm stay in Castelfranco di sopra

Romantic apartment in the Tuscan village

WalkabilityOutdoor spacesKitchen

4.89 out of 5 average rating, 339 reviews

Villa in Monte San Savino

The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.

Villa Tonacato - Charming Villa with private pool

Outdoor spacesWalkabilityPool

4.99 out of 5 average rating, 107 reviews

Private, pet-friendly home rentals

4.95 out of 5 average rating, 295 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 in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

PetsOutdoor spacesParks

4.97 out of 5 average rating, 174 reviews

Villa in Monteriggioni

Villa of the 2 Olive Trees (Abbadia Isola)

WalkabilityOutdoor spacesAir conditioning

Cottage in San Casciano In Val di Pesa

The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.

Il Fienile, Cottage in the country with Jacuzzi

Outdoor spacesWalkabilityComfort

4.96 out of 5 average rating, 194 reviews

Apartment in Castellina in Chianti

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.

Edera

WalkabilityPetsCheck-in

5.0 out of 5 average rating, 29 reviews

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

Outdoor spacesNearbySleep quality

4.98 out of 5 average rating, 84 reviews

Apartment in Castellina in Chianti

A small outdoor seating area features two cushioned chairs and a glass table, surrounded by greenery. A tree branches overhead, providing shade. The charming building's exterior displays rustic stone and warm-toned walls, with open double doors inviting guests inside.

At the Poggio della Capannina in Castellina in Chianti

PetsOutdoor spacesHeating

4.8 out of 5 average rating, 60 reviews

4.96 out of 5 average rating, 47 reviews

beautiful farmhouse in the Chianti region with panoramic garden

Outdoor spacesAccuracyBathroom