
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 $84 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.

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 spacesBreakfast
4.99 out of 5 average rating, 155 reviews
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 spacesWalkabilityAir conditioning
4.93 out of 5 average rating, 255 reviews
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.
Outdoor spacesPetsIndoor spaces
4.9 out of 5 average rating, 136 reviews
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.
PetsWalkabilityView
4.93 out of 5 average rating, 153 reviews
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!
WalkabilityPetsValue
4.93 out of 5 average rating, 293 reviews
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)
WalkabilityPetsHiking
4.88 out of 5 average rating, 153 reviews
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 spacesAccuracy
4.95 out of 5 average rating, 221 reviews
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
PetsOutdoor spacesCleanliness
4.91 out of 5 average rating, 100 reviews
Romantico appartamento nel borgo Toscano
La casa si trova in un antico borgo medioevale completamente ristrutturato pur mantenendo il fascino della sua storia. Nel borgo troverai due piscine, un ristorante, tanti giardini e molto altro... è in una posizione strategica per poter raggiungere le principali attrazioni come la Regione del Chianti, Firenze, Arezzo e Siena!
PetsOutdoor spacesShared spaces
4.89 out of 5 average rating, 343 reviews
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.
WalkabilityOutdoor spacesLaundry
4.98 out of 5 average rating, 129 reviews
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.
WalkabilityPetsComfort
4.88 out of 5 average rating, 128 reviews
La Pieve - the house next to the church
To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?
WalkabilityOutdoor spacesLocation
4.97 out of 5 average rating, 117 reviewsPopular amenities for Gaiole in Chianti pet-friendly home rentals
Pet-friendly house rentals

Agriturismo Casa Giulia di Sopra
Outdoor spacesWalkabilityGetting around
4.95 out of 5 average rating, 106 reviews
Villa Lolù with private heated swimming-pool
PetsWalkabilityQuiet
4.98 out of 5 average rating, 160 reviews
Secret Garden Siena
Outdoor spacesWalkabilityHeating
4.98 out of 5 average rating, 221 reviews
Casa Nataly Chianti - Jeky Stay
PetsWalkabilityTV
4.86 out of 5 average rating, 159 reviews
Casolare nel Chianti, Siena Toscana
Outdoor spacesWalkabilityAccess
4.83 out of 5 average rating, 169 reviews
Podere Piazza casa con vista panoramica
Outdoor spacesPetsHospitality
4.97 out of 5 average rating, 197 reviews
Torretta Apartment
Outdoor spacesWalkabilityHospitality
4.96 out of 5 average rating, 129 reviews
Amore in Chianti
Outdoor spacesWalkabilityParking
4.96 out of 5 average rating, 246 reviewsPet-friendly home rentals with a pool

Villa Capanna, Private Pool, Breathtaking Views
Outdoor spacesWalkabilityLocation
4.89 out of 5 average rating, 309 reviews
Poggio del Fattore-Villa with pool,hilltop,Chianti
Outdoor spacesWalkabilityBreakfast
4.99 out of 5 average rating, 131 reviews
Stunning Tuscan apartment for 2
WalkabilityOutdoor spacesAir conditioning
4.9 out of 5 average rating, 130 reviews
Il Roseto: your Villa in Tuscan Countryside
Outdoor spacesDecorKitchen
4.99 out of 5 average rating, 124 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Outdoor spacesWalkabilityDecor
4.99 out of 5 average rating, 116 reviews
Villa La Doccia, Greve in Chianti.
WalkabilityOutdoor spacesFamily
4.85 out of 5 average rating, 180 reviews
Gli sterpi
PetsOutdoor spacesLong stay
5.0 out of 5 average rating, 100 reviews
Tuscan farmhouse stay with restaurant and pool
Outdoor spacesPetsHeating
4.94 out of 5 average rating, 107 reviewsPrivate, pet-friendly home rentals

Luxury frescoed apartment in the historical center
WalkabilityOutdoor spacesLocation
4.97 out of 5 average rating, 116 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
PetsWalkabilityBiking
5.0 out of 5 average rating, 116 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
Outdoor spacesPetsValue
4.92 out of 5 average rating, 359 reviews
Florence Sunset Hills • Giogoli
Outdoor spacesPetsParking
4.88 out of 5 average rating, 342 reviews
Wonderful house with garden
PetsOutdoor spacesBathroom
4.98 out of 5 average rating, 275 reviews
Rooftop with Breathtaking Views. Short Walk to The Duomo.
Outdoor spacesWalkabilityAir conditioning
4.96 out of 5 average rating, 399 reviews
Villa le Scope 5*
WalkabilityOutdoor spacesKitchen
4.98 out of 5 average rating, 50 reviews
Apartment Comfort | Quiet Escape in Tuscany
Outdoor spacesLocationParking
4.95 out of 5 average rating, 56 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce





