
Pet-friendly holiday rentals in Castiglion Fiorentino
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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 $68 NZD 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, Wifi 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.

The small tower
The proposed farmhouse is a typical terratetto made of characteristic Tuscan stone, ideal for those who want to spend relaxing holidays immersed in the green hills of Castiglione that surround the small valley of Chio. The turret-style building is arranged over three levels: the usable portion of the building is located on the first floor, with a living/dining room and an equipped kitchen, and on the second floor, with a double bedroom, a twin bedroom, and a bathroom with a shower, all furnished with period-style furniture.
PetsWalkabilityCondition

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
PetsOutdoor spacesCleanliness

Cortona’s Rooftop Nest
The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It accommodates 4 people. Fans in the bedrooms The apartment is located in the historic center right in front of the wonderful church of St. Francis and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can accommodate up to 4 people. Fans in the rooms.
Outdoor spacesWalkabilityDecor

Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
PetsOutdoor spacesHot tub

Charming Tuscan Villa with View forFamily&Friends
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!
Outdoor spacesWalkabilityBackyard

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 spacesSleep quality

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 spacesWalkabilityLong stay

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away
WalkabilityOutdoor spacesHiking

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
WalkabilityOutdoor spacesHot tub

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
WalkabilityOutdoor spacesLaundry

Piazza Grande Boutique Apartment
Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.
WalkabilityBreakfastFamily
La Piazzetta - Cozy open space in the historic center of Montepulciano
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. Then go outside and admire the magnificent view of the 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, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.
Outdoor spacesPetsBreakfast
Popular amenities for Castiglion Fiorentino pet-friendly home rentals
Pet-friendly house rentals

Tuscany House | View Breathtaking
Outdoor spacesWalkabilityHeating

La Perla del Lago Holiday home on Lake Trasimeno
PetsWalkabilityBreakfast

Jenny's Barn
WalkabilityOutdoor spacesQuiet

The Loggia
WalkabilityPetsCleanliness

Casa Rosmarino Eco-Wellness Country Home
PetsOutdoor spacesHospitality

Charming house in Cortona, Tuscany
WalkabilityOutdoor spacesIndoor spaces

Traditional stone house in Tuscany
PetsOutdoor spacesKitchen

Secret Garden Siena
WalkabilityPetsLaundry
Pet-friendly home rentals with a pool

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
WalkabilityOutdoor spacesKitchen

Rural Tuscany | Family farmstay with restaurant
Outdoor spacesPetsHeating

Villa Tonacato - Charming Villa with private pool
PetsWalkabilityBathroom

Le Rondini - where it all began
PetsOutdoor spacesCheckout

Romantic apartment in the Tuscan village
Outdoor spacesPetsHospitality
Wp Relais Villa Vignalunga
Outdoor spacesWalkabilityParks

Unique view 3 bdr villa with pool & A/C in Pienza
WalkabilityOutdoor spacesPool

Poggio dell'orso.Traditional Casale. Amazing views
WalkabilityPetsWi-Fi
Private, pet-friendly home rentals

In Tuscany Rooms
Outdoor spacesWalkabilityView

Fontarcella, H&R- mediterranean home with jacuzzi
WalkabilityPetsIndoor spaces

La Casetta di Brunello, very panoramic with terrace
WalkabilityOutdoor spacesSleep quality

Stuart Jasmine central, panoramic top location
Outdoor spacesPetsAmenities

Your Tuscan oak tree house, enchanting Val d'Orcia
WalkabilityOutdoor spacesGetting around

Luxurious Medieval Tower & Private Concierge
Outdoor spacesWalkabilityIndoor spaces

I Tramonti di Eramo, downtown Montepulciano.
WalkabilityParkingCheckout

La Dimora del Luca
Outdoor spacesWalkabilityHospitality
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $182 NZD | $170 NZD | $193 NZD | $187 NZD | $192 NZD | $197 NZD | $246 NZD | $200 NZD | $227 NZD | $292 NZD | $185 NZD | $185 NZD |
| 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
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Basilica of St Francis
- Pitti Palace
- Palazzo Vecchio
- Piazza della Signoria
- Boboli's Garden
- Centro Storico Orvieto
- Mount Amiata
- Medici Chapel
- Stadio Artemio Franchi
- La Scarzuola





