
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 $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 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 Holiday Home overlooks the mirror of Lake Trasimeno. The highway is 8 minutes away, allowing you to visit towns such as Florence, Perugia, Gubbio, Spoleto, Norcia and many others. In the village, you will find cafés, restaurants, a supermarket, a pharmacy, an ATM and children's play areas; 3 km away, there is a beautiful swimming pool where you can relax in summer.
4.98 out of 5 average rating, 207 reviews
The small tower
The farmhouse on offer is a typical terratetto (small farmhouse) built from characteristic Tuscan stone, ideal for those looking to enjoy a relaxing holiday surrounded by the green hills of Castiglioncello that encircle the small valley of Chio. The tower-shaped building is arranged over three levels: the usable part of the property is located on the first floor, with a living/dining room and a fully 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.
4.95 out of 5 average rating, 108 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.
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
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.
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
4.93 out of 5 average rating, 334 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.
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.
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
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.
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.
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.
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
4.99 out of 5 average rating, 273 reviews
Casa del Passerino
4.94 out of 5 average rating, 225 reviews
Traditional stone house in Tuscany
4.97 out of 5 average rating, 102 reviews
La Lisa: country house surrounded by fields
4.94 out of 5 average rating, 135 reviews
Charming house in Cortona, Tuscany
4.95 out of 5 average rating, 203 reviews
Secret Garden Siena
4.98 out of 5 average rating, 221 reviews
The Chianti window
4.9 out of 5 average rating, 136 reviews
Il Vecchio Mulino
4.91 out of 5 average rating, 114 reviewsPet-friendly home rentals with a pool

Villa Capanna, Private Pool, Breathtaking Views
4.89 out of 5 average rating, 309 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
4.91 out of 5 average rating, 100 reviews
Explore nature in the heart of the Chianti vineyards
4.97 out of 5 average rating, 265 reviews
Poggio dell'orso.Traditional Casale. Amazing views
4.96 out of 5 average rating, 169 reviews
The twigs
5.0 out of 5 average rating, 100 reviews
Tuscan Barn Apartment for 6 with panoramic pool
4.89 out of 5 average rating, 100 reviews
Tuscany Villa Mammi
4.99 out of 5 average rating, 90 reviews
Beautiful and cozy country-house, sleeps 11
5.0 out of 5 average rating, 25 reviewsPrivate, pet-friendly home rentals

Poggio Bicchieri Holiday Farm - Poesia apartment
4.95 out of 5 average rating, 579 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
4.98 out of 5 average rating, 168 reviews
Luxury frescoed apartment in the historical center
4.97 out of 5 average rating, 116 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
5.0 out of 5 average rating, 116 reviews
In Tuscany Rooms
4.96 out of 5 average rating, 137 reviews
Mafuccio Farmhouse - "Casa di Rigo"
4.95 out of 5 average rating, 124 reviews
Pendici 15, small apartment
5.0 out of 5 average rating, 41 reviews
Casa La Girandola – Journey through the medieval alleys
4.96 out of 5 average rating, 25 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 | $154 AUD | $159 AUD | $163 AUD | $203 AUD | $166 AUD | $188 AUD | $241 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





