
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 $65 SGD per night before taxes and fees

Verified guest reviews
Over 800 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.

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

Museum Suite - Luxurious unit with a River View -
After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

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.

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
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

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!

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!

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.

Tuscany .Countryhouse on the Florence's hills
Casa recentemente ristrutturata in colonica Toscana dell'800 circondata da colline, vigneti e oliveti situata nella zona del Chianti e distante 1 km dal paese (Antella) e 20 minuti di macchina da Firenze centro. L'alloggio è dotato di raffrescamento per i mesi estivi anche se i muri molto spessi in pietra garantiscono una temperatura gradevole anche in estate.

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.

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.

Secret Garden Siena
A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.
Popular amenities for Castellina in Chianti pet-friendly home rentals
Pet-friendly house rentals

Amore in Chianti

Torretta Apartment

Casolare nel Chianti, Siena Toscana

SuiteLouise.pool, Hot Tub,homeGym & private Garden

La casina ridente in Toscana con vista mozzafiato

Podere Piazza casa con vista panoramica

Casa Dante - Authentic Chianti Stay | Views&Relax

La Casa di Nada Home
Pet-friendly home rentals with a pool

Apartment Ramerino

Il Giglio Relax a Castellina in Chianti

Un fienile nel Chianti

Torre dei Belforti

Esplora la natura al centro di Vigneti Chianti

La Pieve - the house next to the church

Cottage Vittoria - Masseto In Chianti

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Private, pet-friendly home rentals

Gelsomino

Sogno Toscano a Fonterutoli tra Siena e il Chianti

Tuscany jem: La Casa del Fattore del Chianti

Il Fienile, Cottage in the country with Jacuzzi

Al Poggio della Capannina di Castellina in Chianti

Celeste - Il colore del cielo d'estate in Toscana

favolosa colonica nel chianti, giardino panoramico

Appartamento T4
When is the best time to visit Castellina in Chianti?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $186 SGD | $186 SGD | $216 SGD | $216 SGD | $217 SGD | $234 SGD | $229 SGD | $225 SGD | $240 SGD | $216 SGD | $197 SGD | $193 SGD |
| 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
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- Rentals with a patio Castellina in Chianti
- Family-friendly rentals Castellina in Chianti
- Chalet rentals Castellina in Chianti
- Rentals with outdoor seating Castellina in Chianti
- Cottage rentals Castellina in Chianti
- Rentals with a washing machine and dryer Castellina in Chianti
- Villa rentals Castellina in Chianti
- Rentals with pools Castellina in Chianti
- Rentals with a fireplace Castellina in Chianti
- Pet-friendly rentals Tuscany
- Pet-friendly rentals Italy
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Cala Violina
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Spiagge Bianche
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria





