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Pet-friendly holiday rentals in Castellina in Chianti

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Castellina in Chianti

  • Total holiday rentals

    Explore 30 holiday rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 860 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Castellina in Chianti holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

  • 4.8 Average rating

    Castellina in Chianti stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Castellina in Chianti

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
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

PetsOutdoor spacesCondition

4.88 out of 5 average rating, 338 reviews
Guest favourite
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.
Villa in Castellina in Chianti

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

WalkabilityOutdoor spacesCondition

4.93 out of 5 average rating, 254 reviews
Top guest favourite
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.

Outdoor spacesPetsTV

4.99 out of 5 average rating, 155 reviews
Guest favourite
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.
Home in Castelnuovo Berardenga

La finestra del Chianti

Un luogo meraviglioso dove trascorrere alcuni giorni in piacevole compagnia. Un ampio salone con camino dove rilassarsi al rientro da bellissime passeggiate, giri in bicicletta, ed escursioni. L'appartamento indipendente si trova a 15km da Siena, 20 km dai centri Termali e a 40 minuti dai borghi di san Gimignano e Monteriggioni. Nel complesso è presente un'azienda agricola che produce vini e olio con la possibilità di visite guidate e degustazione dei nostri prodotti con cene a tema.

PetsOutdoor spacesIndoor spaces

4.9 out of 5 average rating, 133 reviews
Top guest favourite
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 - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

PetsOutdoor spacesRiver

4.97 out of 5 average rating, 194 reviews
Superhost
Home in Barberino Tavarnelle

La Casa di 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 🌷

PetsOutdoor spacesValue

4.87 out of 5 average rating, 215 reviews
Top guest favourite
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.
Flat in Gavignano

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

WalkabilityPetsCleanliness

4.92 out of 5 average rating, 386 reviews
Top guest favourite
Cottage in Castellina in Chianti

Cottage Leccio - 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).

Outdoor spacesWalkabilitySleep quality

4.96 out of 5 average rating, 102 reviews
Top guest favourite
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.
Home in Barberino Tavarnelle

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!

WalkabilityOutdoor spacesLaundry

4.96 out of 5 average rating, 330 reviews
Top guest favourite
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.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

WalkabilityOutdoor spacesCondition

4.95 out of 5 average rating, 219 reviews
Guest favourite
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.
Castle in Barberino Tavarnelle

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.

WalkabilityPetsAmenities

4.88 out of 5 average rating, 126 reviews
Guest favourite
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.
Flat in Castellina in Chianti

Casa Tatini la tua casa in Chianti

Casa Tatini si trova nel cuore del Chianti a soli 500 metri da Castellina in Chianti in mezzo alle viti e alla natura, per rilassarsi nel verde. La casa, dotata di piscina, è composta da una camera matrimoniale, soggiorno con cucina e bagno privato.

WalkabilityOutdoor spacesLaundry

4.91 out of 5 average rating, 140 reviews

Popular amenities for Castellina in Chianti pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Superhost
A bright living area features a wooden coffee table at its center, flanked by a light-colored sofa and a darker green couch. Two windows with wooden shutters offer views of the surrounding vineyards, while exposed wooden beams add character to the ceiling.
Home in Greve in Chianti

Country Rentals - La Canonica

WalkabilityOutdoor spacesPool

4.86 out of 5 average rating, 101 reviews
Top guest favourite
Home in Il Poggetto

La Loggia

PetsOutdoor spacesBiking

4.93 out of 5 average rating, 152 reviews
Guest favourite
Home in Barberino Tavarnelle

SuiteLouise.pool, Hot Tub,homeGym & private Garden

PetsOutdoor spacesAccuracy

4.91 out of 5 average rating, 124 reviews
Top guest favourite
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

PetsOutdoor spacesParking

4.98 out of 5 average rating, 218 reviews
Guest favourite
Home in Monteriggioni

Next to castle of Villa-Siena. heart Francigena

PetsWalkabilityHeating

4.83 out of 5 average rating, 157 reviews
Top guest favourite
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 – n. 8 Casa Vecchia

PetsOutdoor spacesLocation

4.95 out of 5 average rating, 200 reviews
Top guest favourite
Home in Terranuova Bracciolini

Villa Lolù with private heated swimming-pool

WalkabilityPetsHot tub

4.97 out of 5 average rating, 159 reviews
Guest favourite
An aerial view captures a rustic countryside villa nestled within lush greenery and olive groves. The structure features a tiled roof and surrounded by trees, with a separate building visible nearby. The serene landscape enhances the sense of privacy and tranquility.
Home in Montespertoli

Costalmandorlo, rustico nel cuore della Toscana

Outdoor spacesWalkabilityBreakfast

4.91 out of 5 average rating, 126 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 spacesWalkabilityKitchen

4.85 out of 5 average rating, 179 reviews
Top guest favourite
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.
Holiday home in Panzano in Chianti

Fienile Santa Teresa

WalkabilityOutdoor spacesPool

4.98 out of 5 average rating, 174 reviews
Guest favourite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Outdoor spacesWalkabilityLong stay

4.89 out of 5 average rating, 307 reviews
Top guest favourite
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.
Farm stay in Monte San Savino

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Outdoor spacesWalkabilityGetting around

4.99 out of 5 average rating, 113 reviews
Guest favourite
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.
Farm stay in Badia a Passignano

Un fienile nel Chianti

PetsWalkabilityAmenities

4.8 out of 5 average rating, 252 reviews
Guest favourite
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.
Flat in Castellina in Chianti

Appartamento T4

WalkabilityPetsKitchen

4.87 out of 5 average rating, 75 reviews
Superhost
A well-appointed villa is situated on an open ridge, surrounded by lush greenery. The private pool, equipped with sun loungers, is framed by vibrant gardens. The structure combines rustic charm with scenic views of the Tuscan landscape, offering a tranquil retreat.
Villa in Castellina in Chianti

Casanovina

Outdoor spacesWalkabilityComfort

4.92 out of 5 average rating, 12 reviews
Top guest favourite
The villa is depicted with a stone exterior, surrounded by olive trees and rolling vineyards. A circular pool is featured in the foreground, offering a tranquil spot for relaxation. Umbrellas provide shade over lounge chairs nearby, enhancing the serene outdoor space.
Villa in Radda in Chianti

Villa con piscina nel Chianti - Castellare Petroso

Outdoor spacesAir conditioningWifi

5.0 out of 5 average rating, 33 reviews

Private, pet-friendly home rentals

Guest favourite
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

Outdoor spacesWalkabilityParking

4.95 out of 5 average rating, 295 reviews
Top guest favourite
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.
Cottage in San Casciano In Val di Pesa

Il Fienile, Cottage in the country with Jacuzzi

WalkabilityOutdoor spacesWifi

4.96 out of 5 average rating, 194 reviews
Guest favourite
Villa in Monteriggioni

Villa dei 2 Ulivi (Abbadia Isola)

WalkabilityPetsBiking

4.97 out of 5 average rating, 174 reviews
Top guest favourite
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.
Flat in Castellina in Chianti

Edera

PetsWalkabilitySleep quality

5.0 out of 5 average rating, 29 reviews
Top guest favourite
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.
Flat in Quercegrossa

Tuscany jem: La Casa del Fattore del Chianti

Outdoor spacesConditionComfort

4.98 out of 5 average rating, 84 reviews
Guest favourite
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.
Flat in Castellina in Chianti

Al Poggio della Capannina di Castellina in Chianti

WalkabilityPetsAccuracy

4.8 out of 5 average rating, 60 reviews
Guest favourite
Home in Barberino Tavarnelle

splendida colonica nel chianti giardino panoramico

Outdoor spacesAccuracyFamily

4.96 out of 5 average rating, 47 reviews
Guest favourite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti

Villa le Scope 5*

Outdoor spacesPetsSleep quality

4.98 out of 5 average rating, 49 reviews

When is the best time to visit Castellina in Chianti?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$183 SGD$183 SGD$213 SGD$223 SGD$233 SGD$233 SGD$225 SGD$222 SGD$237 SGD$213 SGD$194 SGD$190 SGD
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Destinations to explore