
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 $69 AUD 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 and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Castellina in Chianti holiday rentals include Wi-Fi 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.

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!
Outdoor spacesWalkabilityAmenities

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 spacesKitchen

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 spacesPetsHeating

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 spacesHeating

Casa Giulia di Sopra Farmhouse
The CASA GIULIA DI SOPRA apartment, renovated in 2022 and located on the first floor, is a portion of an ancient farmhouse located in the heart of Chianti Classico. It is surrounded by the vineyards of Villa Calcinaia, an estate owned by the Capponi Counts since 1524. The apartment is 130 meters away from the shared swimming pool, open from May to October. The apartment has an outdoor area with a table and chairs where guests can dine and enjoy a glass of wine at sunset.
Outdoor spacesWalkabilityPool

Villa La Doccia, Greve in Chianti
Villa La Doccia is located approximately 8 minutes by car from the centre of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet, peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscape. The location is perfect for those who want to relax in the countryside while still being close to the centre of Greve in Chianti.
WalkabilityOutdoor spacesAccuracy

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.
PetsOutdoor spacesAccuracy

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 🌷
WalkabilityPetsAccuracy
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).
Outdoor spacesWalkabilityAmenities

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!
PetsWalkabilityParking

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.
Outdoor spacesWalkabilityCheckout

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.
Outdoor spacesPetsHiking
Popular amenities for Castellina in Chianti pet-friendly home rentals
Pet-friendly house rentals

Farmhouse in Chianti, Siena Tuscany
WalkabilityOutdoor spacesLocation

Borgo Ripostena – No. 8 Casa Vecchia
Outdoor spacesPetsCheckout

The Chianti window
Outdoor spacesPetsAccess

SuiteLouise.pool, Hot Tub,homeGym & private Garden
Outdoor spacesPetsBreakfast

Love in Chianti
PetsOutdoor spacesLaundry

Secret Garden Siena
Outdoor spacesPetsKitchen

The Loggia
WalkabilityPetsHeating

TREEhouse / casaBARTHEL
PetsWalkabilityCheck-in
Pet-friendly home rentals with a pool

Fienile Santa Teresa
WalkabilityPetsDecor

Romantic apartment in the Tuscan village
WalkabilityOutdoor spacesPool

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Outdoor spacesWalkabilityFamily

Villa Capanna, Private Pool, Breathtaking Views
WalkabilityOutdoor spacesDecor

A barn in Chianti
Outdoor spacesPetsBreakfast

Apartment T4
PetsWalkabilityCleanliness

Casanovina
WalkabilityOutdoor spacesCleanliness

Exclusive villa with swimming pool in the Chianti Classico area
Outdoor spacesPoolBathroom
Private, pet-friendly home rentals

Wonderful house with garden
WalkabilityOutdoor spacesLong stay

Monteriggioni Castello, holiday house in Tuscany
WalkabilityOutdoor spacesIndoor spaces

Il Fienile, Cottage in the country with Jacuzzi
WalkabilityOutdoor spacesLocation

Edera
PetsWalkabilityValue

Tuscany jem: The Chianti Farmer's House
Outdoor spacesBathroomFamily

beautiful farmhouse in the Chianti region with panoramic garden
Outdoor spacesFamilyComfort

At the Poggio della Capannina in Castellina in Chianti
Outdoor spacesPetsBathroom

The Chianti Cabin
WalkabilityOutdoor spacesView
When is the best time to visit Castellina in Chianti?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 AUD | $200 AUD | $232 AUD | $243 AUD | $254 AUD | $254 AUD | $246 AUD | $242 AUD | $259 AUD | $232 AUD | $211 AUD | $207 AUD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Destinations to explore
- House rentals Castellina in Chianti
- Apartment rentals Castellina in Chianti
- Family-friendly rentals Castellina in Chianti
- Chalet rentals Castellina in Chianti
- Cottage rentals Castellina in Chianti
- Villa rentals Castellina in Chianti
- Rentals with pools Castellina in Chianti
- Pet-friendly rentals Tuscany
- Pet-friendly rentals Italy
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Cala Violina
- Stazione Santa Maria Novella
- Spiagge Bianche
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





