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

Total vacation rentals
Explore 60 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at G$8,372 GYD per night before taxes and fees

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

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Vacation 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 vacation 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.

La Perla del Lago Holiday home on Lake Trasimeno
La Perla del Lago: your refuge at Trasimeno Rediscover your harmony in this oasis of absolute peace. Let yourself be enchanted by our magical view and the sunsets that the lake offers every evening. The La Perla del Lago Vacation Home overlooks the mirror of Lake Trasimeno. 8 minutes away you will find the highway to visit towns such as Florence, Perugia, Gubbio, Spoleto, Norcia and many others. In the village, you will find cafés, restaurants, a market, a pharmacy, ATMs, and children's play areas; 3 km away, there is a beautiful swimming pool for summer relaxation.
WalkabilityPetsNearby
4.98 out of 5 average rating, 207 reviews
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.
WalkabilityPetsLocation
4.95 out of 5 average rating, 109 reviews
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.
WalkabilityOutdoor spacesNearby
4.99 out of 5 average rating, 189 reviews
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
Outdoor spacesPetsCheckout
4.9 out of 5 average rating, 241 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.
WalkabilityOutdoor spacesTV
4.97 out of 5 average rating, 251 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
WalkabilityOutdoor spacesCleanliness
4.93 out of 5 average rating, 335 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
WalkabilityOutdoor spacesView
4.95 out of 5 average rating, 146 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.
Outdoor spacesWalkabilityAccuracy
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
WalkabilityPetsWifi
4.8 out of 5 average rating, 110 reviews
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.
WalkabilityKitchenAir conditioning
5.0 out of 5 average rating, 155 reviews
Rural Tuscany | Family farmstay with restaurant
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.
PetsOutdoor spacesLong stay
4.96 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.
WalkabilityTVKitchen
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
Outdoor spacesPetsFamily
4.99 out of 5 average rating, 273 reviews
Casa del Passerino
WalkabilityCleanlinessValue
4.94 out of 5 average rating, 225 reviews
Traditional stone house in Tuscany
PetsOutdoor spacesIndoor spaces
4.97 out of 5 average rating, 102 reviews
La Lisa: country house surrounded by fields
Outdoor spacesPetsHeating
4.94 out of 5 average rating, 135 reviews
Charming house in Cortona, Tuscany
WalkabilityPetsHospitality
4.95 out of 5 average rating, 203 reviews
Secret Garden Siena
PetsWalkabilityCheckout
4.98 out of 5 average rating, 221 reviews
The Chianti window
PetsOutdoor spacesAccess
4.9 out of 5 average rating, 136 reviews
Il Vecchio Mulino
WalkabilityOutdoor spacesParking
4.91 out of 5 average rating, 114 reviewsPet-friendly home rentals with a pool

Villa Capanna, Private Pool, Breathtaking Views
WalkabilityOutdoor spacesCleanliness
4.89 out of 5 average rating, 309 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Outdoor spacesPetsParking
4.91 out of 5 average rating, 100 reviews
Esplora la natura al centro di Vigneti Chianti
Outdoor spacesPetsValue
4.97 out of 5 average rating, 265 reviews
Poggio dell'orso.Traditional Casale. Amazing views
WalkabilityOutdoor spacesBathroom
4.96 out of 5 average rating, 169 reviews
Gli sterpi
Outdoor spacesPetsSleep quality
5.0 out of 5 average rating, 100 reviews
Tuscan Barn Apartment for 6 with panoramic pool
PetsWalkabilityHospitality
4.89 out of 5 average rating, 100 reviews
Tuscany Villa Mammi
Outdoor spacesWalkabilityGetting around
4.99 out of 5 average rating, 90 reviews
Beautiful and cozy country-house, sleeps 11
Outdoor spacesCheck-inKitchen
5.0 out of 5 average rating, 25 reviewsPrivate, pet-friendly home rentals

Poggio Bicchieri Holiday Farm - Poesia Apartment
PetsOutdoor spacesBackyard
4.95 out of 5 average rating, 579 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
Outdoor spacesWalkabilityView
4.98 out of 5 average rating, 168 reviews
Luxury frescoed apartment in the historical center
Outdoor spacesWalkabilityHeating
4.97 out of 5 average rating, 116 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
PetsOutdoor spacesCheckout
5.0 out of 5 average rating, 116 reviews
In Toscana Camere
Outdoor spacesPetsAccess
4.96 out of 5 average rating, 137 reviews
Mafuccio Farmhouse - "Casa di Rigo"
Outdoor spacesWalkabilityGetting around
4.95 out of 5 average rating, 124 reviews
Pendici 15, small apartment
Outdoor spacesPetsComfort
5.0 out of 5 average rating, 41 reviews
Casa La Girandola – Journey through the medieval alleys
WalkabilityOutdoor spacesLocation
4.96 out of 5 average rating, 25 reviewsWhen is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,396 GYD | G$20,931 GYD | G$23,862 GYD | G$23,024 GYD | G$23,652 GYD | G$24,280 GYD | G$30,350 GYD | G$24,699 GYD | G$28,048 GYD | G$36,002 GYD | G$22,815 GYD | G$22,815 GYD |
| 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





