
Pet-friendly holiday rentals in Castiglion Fiorentino
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Castiglion Fiorentino

Total holiday rentals
Explore 60 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at $56 AUD per night before taxes and fees

Verified guest reviews
Over 1,250 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Castiglion Fiorentino holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Castiglion Fiorentino rentals

4.8 Average rating
Castiglion Fiorentino stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated pet-friendly home rentals in Castiglion Fiorentino
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

La Perla del Lago Casa vacanze al Lago Trasimeno
La Perla del Lago:il tuo rifugio al Trasimeno Ritrova la tua armonia in questa oasi di pace assoluta. Lasciati incantare dalla nostra vista magica e dai tramonti che il Lago regala ogni sera. La Casa Vacanze La Perla del Lago domina lo specchio del Trasimeno. A 8 minuti trovi la superstrada per visitare borghi come Firenze, Perugia, Gubbio, Spoleto, Norcia e molti altri. Nel borgo avrai bar,ristoranti,market, farmacia, bancomat e aree bimbi;a 3 km sorge un'azzurra piscina per il relax estivo.
WalkabilityOutdoor spacesCheck-in
4.98 out of 5 average rating, 207 reviews
Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.
Outdoor spacesPetsSleep quality
4.97 out of 5 average rating, 251 reviews
Agriturismo Poggio Bicchieri ap. Memoria
Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!
WalkabilityPetsHeating
4.92 out of 5 average rating, 626 reviews
Tuscan charm of villa - countryside - Villa Senaia
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale
Outdoor spacesPetsFamily
4.9 out of 5 average rating, 240 reviews
La piccola torretta
Il casale proposto è un tipico terratetto realizzato in caratteristica pietra toscana, ideale per chi vuole trascorrere vacanze rilassanti immersi nel verde delle colline castiglionesi che cingono la piccola valle di Chio. Lo stabile, a torretta, è disposto su tre livelli: la porzione di fabbricato utilizzabile è posta al piano primo con soggiorno/pranzo e cucina attrezzata ed al piano secondo con camera matrimoniale, camera doppia e bagno con doccia, il tutto arredato con mobili in stile.
WalkabilityPetsHiking
4.95 out of 5 average rating, 109 reviews
Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
WalkabilityPetsHeating
4.92 out of 5 average rating, 337 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.
WalkabilityOutdoor spacesBreakfast
4.99 out of 5 average rating, 116 reviews
Tuscan Villa Luigina with Pool & Panoramic View
If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX
Outdoor spacesWalkabilityLong stay
4.8 out of 5 average rating, 110 reviews
Tuscan farmhouse stay with restaurant and pool
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
Outdoor spacesWalkabilityGetting around
4.94 out of 5 average rating, 108 reviews
Piazza Grande Boutique Apartment
Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.
WalkabilityAccessAccuracy
5.0 out of 5 average rating, 155 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.
Outdoor spacesPetsGetting around
5.0 out of 5 average rating, 116 reviews
Modern apartment in the heart of Tuscany
A few steps from Castiglion Fiorentino train station. Ideal for exploring not only this charming medieval city but also other beautiful Tuscan cities, such as Arezzo, Cortona and Siena. The apartment has 1 bathroom and 5 beds, ideal for families or groups of friends. There is also an additional sofa bed for extra guests. It also has a small loggia for relaxing. Its central location allows you to easily find services such as shops, restaurants and bars nearby.
WalkabilityParkingLocation
4.93 out of 5 average rating, 109 reviewsPopular amenities for Castiglion Fiorentino pet-friendly home rentals
Pet-friendly house rentals

Casa Rosmarino Eco-Wellness Country Home
PetsOutdoor spacesLaundry
4.99 out of 5 average rating, 274 reviews
La finestra del Chianti
PetsOutdoor spacesCheckout
4.9 out of 5 average rating, 136 reviews
Charming house in Cortona, Tuscany
WalkabilityOutdoor spacesNearby
4.95 out of 5 average rating, 203 reviews
Jenny's Barn
WalkabilityPetsEV charging
4.96 out of 5 average rating, 187 reviews
Traditional stone house in Tuscany
Outdoor spacesPetsBathroom
4.97 out of 5 average rating, 102 reviews
La Lisa: country house surrounded by fields
WalkabilityPetsAccuracy
4.94 out of 5 average rating, 135 reviews
Secret Garden Siena
PetsOutdoor spacesCleanliness
4.98 out of 5 average rating, 221 reviews
Infinity view
WalkabilityOutdoor spacesDecor
4.88 out of 5 average rating, 204 reviewsPet-friendly home rentals with a pool

Gli sterpi
WalkabilityOutdoor spacesView
5.0 out of 5 average rating, 100 reviews
Romantico appartamento nel borgo Toscano
PetsWalkabilityPool
4.89 out of 5 average rating, 343 reviewsWp Relais Villa Vignalunga
Outdoor spacesPetsFamily
4.93 out of 5 average rating, 117 reviews
Castello di Spedaletto, Val d'Orcia, Pienza
PetsOutdoor spacesAccuracy
4.97 out of 5 average rating, 185 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
WalkabilityOutdoor spacesComfort
4.95 out of 5 average rating, 104 reviews
Esplora la natura al centro di Vigneti Chianti
PetsOutdoor spacesHeating
4.97 out of 5 average rating, 265 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
PetsOutdoor spacesHeating
4.91 out of 5 average rating, 100 reviews
Poggio dell'orso.Traditional Casale. Amazing views
Outdoor spacesWalkabilityLong stay
4.96 out of 5 average rating, 170 reviewsPrivate, pet-friendly home rentals

Casale in pietra in Val D’Orcia
WalkabilityPetsIndoor spaces
4.98 out of 5 average rating, 160 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
Outdoor spacesPetsIndoor spaces
4.98 out of 5 average rating, 169 reviews
Villa di Geggiano - Guesthouse
Outdoor spacesPetsComfort
4.99 out of 5 average rating, 155 reviews
Under the sunset, Montepulciano
Outdoor spacesWalkabilityBathroom
4.98 out of 5 average rating, 165 reviews
Agriturismo Mafuccio - "Casa di Rigo"
WalkabilityOutdoor spacesGetting around
4.94 out of 5 average rating, 125 reviews
Luxury frescoed apartment in the historical center
Outdoor spacesWalkabilityHeating
4.97 out of 5 average rating, 116 reviews
La Dimora del Luca
WalkabilityPetsIndoor spaces
4.98 out of 5 average rating, 171 reviews
I Tramonti di Eramo, Montepulciano centro.
WalkabilityAir conditioningCheck-in
4.91 out of 5 average rating, 310 reviewsWhen is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $150 AUD | $140 AUD | $160 AUD | $155 AUD | $159 AUD | $163 AUD | $204 AUD | $166 AUD | $188 AUD | $242 AUD | $153 AUD | $153 AUD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations 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
- 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
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Medici Chapel





