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Pet-friendly holiday rentals in Gaiole in Chianti

Find and book unique pet-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 20 holiday rentals in Gaiole in Chianti

  • Nightly prices starting at

    Gaiole in Chianti holiday rentals start at $86 AUD per night before taxes and fees

  • Verified guest reviews

    Over 590 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Gaiole in Chianti holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Gaiole in Chianti rentals

  • 4.8 Average rating

    Gaiole in Chianti stays are highly rated by guests—averaging 4.8 out of 5!

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

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

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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.

PetsOutdoor spacesBackyard

4.99 out of 5 average rating, 155 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

Outdoor spacesWalkabilityLaundry

4.93 out of 5 average rating, 256 reviews
Superhost
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 spacesQuiet

4.91 out of 5 average rating, 137 reviews
Top Guest favourite
Home in Il Poggetto

La Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

WalkabilityOutdoor spacesAccuracy

4.93 out of 5 average rating, 155 reviews
Top Guest favourite
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.
Farm stay in Simignano

Casa al Gianni - Capanna

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Outdoor spacesWalkabilityLocation

4.93 out of 5 average rating, 295 reviews
Guest favourite
A well-equipped kitchen area features light cream cabinetry and modern appliances. A wooden dining table is surrounded by white chairs, with a centerpiece of flowers. Natural light filters through the sheer curtains of the window, enhancing the inviting ambiance of the space.
Apartment in Gaiole in Chianti

Casa Martini nel Chianti Storico

Appartamento con giardino e parcheggio privato a Gaiole in Chianti, a due passi dal centro storico dove troverete numerosi bar ristoranti ed il piccolo supermercato ( coop). l'alloggio è ideale per vacanze con animali perché è dotato di un giardino tutto recintato. Viene richiesta la tassa di soggiorno ( 2 euro a persona a notte per le prime sette notti) minori di 14 anni esclusi ( leggi regolamento completo nel sito internet del Comune di Gaiole in Chianti)

PetsWalkabilityQuiet

4.88 out of 5 average rating, 154 reviews
Top Guest favourite
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.

Outdoor spacesWalkabilitySleep quality

4.97 out of 5 average rating, 117 reviews
Guest favourite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Outdoor spacesWalkabilityPool

4.89 out of 5 average rating, 311 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.

Outdoor spacesWalkabilityLocation

4.95 out of 5 average rating, 222 reviews
Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

PetsWalkabilityGetting around

4.91 out of 5 average rating, 101 reviews
Top Guest favourite
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

L appartamento Casa Guardiavigna offre la possibilita’ di vivere un esperienza unica e straordinaria, carica di emozioni e di felicita’. Situato a due passi dal piccolo borgo medievale di San Gusme’ e’ circondato da splendide vigne, boschi e prati fioriti. Parcheggio gratuito interno con cancello automatico.

Outdoor spacesWalkabilityQuiet

4.98 out of 5 average rating, 130 reviews
Top 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.

Outdoor spacesWalkabilityQuiet

4.88 out of 5 average rating, 129 reviews

Popular amenities for Gaiole in Chianti pet-friendly home rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top Guest favourite
Home in Terranuova Bracciolini

Villa Lolù with private heated swimming-pool

Outdoor spacesPetsBarbecue

4.98 out of 5 average rating, 161 reviews
Superhost
Home in Villa A Sesta

Casa Nataly Chianti - Jeky Stay

WalkabilityPetsAir conditioning

4.86 out of 5 average rating, 160 reviews
Guest favourite
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

Agriturismo Casa Giulia di Sopra

Outdoor spacesWalkabilityAmenities

4.95 out of 5 average rating, 107 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 spacesLaundry

4.98 out of 5 average rating, 222 reviews
Guest favourite
A charming stone farmhouse is showcased, featuring traditional architecture with a tiled roof and multiple windows. A wheelbarrow filled with flowers is positioned on the grassy front lawn, complemented by potted plants and an outdoor light fixture, enhancing the rural setting.
Home in Quercegrossa

Casolare nel Chianti, Siena Toscana

WalkabilityOutdoor spacesFamily

4.83 out of 5 average rating, 169 reviews
Top Guest favourite
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.
Home in Figline e Incisa Valdarno

Torretta Apartment

Outdoor spacesWalkabilityParking

4.96 out of 5 average rating, 129 reviews
Guest favourite
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

Amore in Chianti

PetsOutdoor spacesCheck-in

4.96 out of 5 average rating, 249 reviews
Top Guest favourite
Home in Siena

Podere Piazza casa con vista panoramica

PetsWalkabilityAccuracy

4.97 out of 5 average rating, 197 reviews

Pet-friendly home rentals with a pool

Guest favourite
Farm stay in Castelfranco di sopra

Romantico appartamento nel borgo Toscano

WalkabilityOutdoor spacesSolo travel

4.89 out of 5 average rating, 346 reviews
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 spacesWalkabilityAccuracy

4.85 out of 5 average rating, 180 reviews
Top Guest favourite
The stone farmhouse features vibrant red shutters and a terracotta roof. A spacious patio area contains a wooden dining set, surrounded by lush green grass and tall cypress trees. The exterior is complemented by well-maintained stone pathways, inviting guests to explore the outdoor space.
Villa in San Leolino

Poggio del Fattore-Villa with pool,hilltop,Chianti

PetsWalkabilityLong stay

4.99 out of 5 average rating, 131 reviews
Top Guest favourite
The exterior of the villa is showcased, featuring stone walls and greenery. A spacious stone patio is visible, furnished with a dining table and chairs, surrounded by neatly trimmed bushes and potted plants, creating an inviting space for outdoor gatherings.
Farm stay in Loro Ciuffenna

Il Roseto: your Villa in Tuscan Countryside

Outdoor spacesAccuracyGetting around

4.99 out of 5 average rating, 124 reviews
Top Guest favourite
A charming stone cottage is set among lush green hills, featuring large arched windows and a shaded patio area with outdoor seating. Olive trees surround the property, providing a connection to the natural landscape, while a gravel pathway leads to the entrance.
Villa in Sinalunga

Gli sterpi

PetsOutdoor spacesCleanliness

5.0 out of 5 average rating, 100 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

WalkabilityOutdoor spacesLayout

4.99 out of 5 average rating, 116 reviews
Guest favourite
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 in Greve in Chianti

Stunning Tuscan apartment for 2

WalkabilityPetsNearby

4.9 out of 5 average rating, 131 reviews
Guest favourite
The crystal-clear swimming pool reflects the blue sky, bordered by a well-kept garden. In the background, a stone farmhouse features green shutters and a classic tiled roof. The pool area is complemented by shaded seating, offering a serene and private atmosphere.
Villa in Gaiole in Chianti

Podere il Trebbio

Outdoor spacesWalkabilityView

4.92 out of 5 average rating, 88 reviews

Private, pet-friendly home rentals

Top Guest favourite
Farm stay in Siena

Typical Tuscan Country House WITH A/C

Outdoor spacesWalkabilityKitchen

4.98 out of 5 average rating, 294 reviews
Top Guest favourite
Townhouse in Scandicci

Florence Sunset Hills • Giogoli

WalkabilityOutdoor spacesLong stay

4.88 out of 5 average rating, 343 reviews
Guest favourite
Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

WalkabilityOutdoor spacesFamily

4.92 out of 5 average rating, 359 reviews
Top Guest favourite
A light-filled living area features curved ceilings and large arched windows opening to a garden. A comfortable armchair and a striped sofa are arranged around a neutral coffee table. Bookshelves line the walls, displaying an assortment of decorative items and books.
Apartment in Santo Spirito

Wonderful house with garden

WalkabilityOutdoor spacesLayout

4.98 out of 5 average rating, 275 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*

PetsWalkabilityGetting around

4.98 out of 5 average rating, 50 reviews
Guest favourite
A serene bedroom features two single beds that can be combined into a double, complemented by soft pillows and warm bedding. Natural light filters through the window, adorned with patterned curtains. Rustic decor includes wooden accents and artwork on the walls, enhancing the inviting atmosphere.
Apartment in Radda in Chianti

La Capannina del Chianti

Outdoor spacesWalkabilityLaundry

4.96 out of 5 average rating, 67 reviews
Guest favourite
Condo in Radda in Chianti

Appartamento Holly House

Outdoor spacesViewCleanliness

4.95 out of 5 average rating, 20 reviews
Guest favourite
Apartment in Cavriglia

Apartment Comfort | Quiet Escape in Tuscany

Outdoor spacesIndoor spacesAir conditioning

4.93 out of 5 average rating, 60 reviews

Destinations to explore