
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 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 spacesWalkabilityAmenities
4.93 out of 5 average rating, 255 reviews
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 spacesAir conditioning
4.99 out of 5 average rating, 155 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 spacesPetsHeating
4.9 out of 5 average rating, 136 reviews
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!
WalkabilityPetsLayout
4.97 out of 5 average rating, 198 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.
WalkabilityOutdoor spacesLaundry
4.93 out of 5 average rating, 153 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)
PetsOutdoor spacesLaundry
4.88 out of 5 average rating, 153 reviews
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.
WalkabilityOutdoor spacesKitchen
4.97 out of 5 average rating, 116 reviews
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 spacesWalkabilityValue
4.89 out of 5 average rating, 309 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.
Outdoor spacesWalkabilityCheck-in
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
WalkabilityOutdoor spacesSleep quality
4.91 out of 5 average rating, 100 reviews
Villa Lolù with private heated swimming-pool
Affascinante villa con piscina privata riscaldata, e con vasca idromassaggio all'aperto. Grandissima casa di mq.175 con cucina, sala da pranzo, sala con caminetto, 3 camere matrimoniali, 1 camera con 2 letti singoli , 1 divano letto matrimoniale, 3 bagni di cui uno en suite. Da quest'anno è presente anche una palestra
WalkabilityPetsAmenities
4.98 out of 5 average rating, 160 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.
Outdoor spacesWalkabilityBreakfast
4.98 out of 5 average rating, 129 reviewsPopular amenities for Gaiole in Chianti pet-friendly home rentals
Pet-friendly house rentals

Secret Garden Siena
WalkabilityPetsQuiet
4.98 out of 5 average rating, 221 reviews
Casolare nel Chianti, Siena Toscana
WalkabilityOutdoor spacesCleanliness
4.83 out of 5 average rating, 168 reviews
Country Rentals - La Canonica
WalkabilityOutdoor spacesIndoor spaces
4.86 out of 5 average rating, 101 reviews
Casa Nataly Chianti - Jeky Stay
WalkabilityOutdoor spacesBathroom
4.86 out of 5 average rating, 159 reviews
La Casa di Nada Home
WalkabilityOutdoor spacesAir conditioning
4.87 out of 5 average rating, 217 reviews
Torretta Apartment
WalkabilityOutdoor spacesSleep quality
4.96 out of 5 average rating, 129 reviews
Podere Piazza casa con vista panoramica
Outdoor spacesPetsCheck-in
4.97 out of 5 average rating, 197 reviews
Borgo Ripostena – n. 8 Casa Vecchia
Outdoor spacesPetsView
4.95 out of 5 average rating, 202 reviewsPet-friendly home rentals with a pool

Poggio del Fattore-Villa with pool,hilltop,Chianti
WalkabilityPetsView
4.99 out of 5 average rating, 131 reviews
Villa La Doccia, Greve in Chianti.
Outdoor spacesPetsWi-Fi
4.85 out of 5 average rating, 180 reviews
Romantico appartamento nel borgo Toscano
Outdoor spacesPetsAccess
4.89 out of 5 average rating, 343 reviews
Rural Tuscany | Family farmstay with restaurant
WalkabilityPetsBathroom
4.96 out of 5 average rating, 116 reviews
Il Roseto: your Villa in Tuscan Countryside
Outdoor spacesLocationAir conditioning
4.99 out of 5 average rating, 124 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Outdoor spacesWalkabilityBarbecue
4.99 out of 5 average rating, 116 reviews
Cottage Cappero - Masseto In Chianti
WalkabilityOutdoor spacesLocation
4.97 out of 5 average rating, 115 reviews
Poggio Massiccioli
PetsOutdoor spacesHeating
4.92 out of 5 average rating, 389 reviewsPrivate, pet-friendly home rentals

Amazing Tuscany Villa, FREE parking
WalkabilityOutdoor spacesKitchen
4.93 out of 5 average rating, 335 reviews
Florence Sunset Hills • Giogoli
Outdoor spacesWalkabilityCheck-in
4.88 out of 5 average rating, 342 reviews
Il Fienile, Cottage in the country with Jacuzzi
PetsOutdoor spacesNearby
4.96 out of 5 average rating, 198 reviews
Suite in Castello di Valle
Outdoor spacesPetsWi-Fi
4.88 out of 5 average rating, 128 reviews
Typical Tuscan Country House WITH A/C
PetsOutdoor spacesWi-Fi
4.98 out of 5 average rating, 294 reviews
Villa le Scope 5*
WalkabilityPetsFamily
4.98 out of 5 average rating, 50 reviews
Tuscany jem: La Casa del Fattore del Chianti
Outdoor spacesPoolSleep quality
4.98 out of 5 average rating, 88 reviews
Villa Eroica
WalkabilityOutdoor spacesHospitality
4.97 out of 5 average rating, 32 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





