
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.

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
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!
4.92 out of 5 average rating, 625 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
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
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.
4.94 out of 5 average rating, 107 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 reviews
Casa del Passerino
Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!
4.94 out of 5 average rating, 225 reviewsPopular amenities for Castiglion Fiorentino pet-friendly home rentals
Pet-friendly house rentals

La Perla del Lago Holiday home on Lake Trasimeno
4.98 out of 5 average rating, 206 reviews
The Chianti window
4.9 out of 5 average rating, 135 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, 220 reviews
Il Vecchio Mulino
4.91 out of 5 average rating, 114 reviews
Farmhouse in Chianti, Siena Tuscany
4.83 out of 5 average rating, 168 reviewsPet-friendly home rentals with a pool

Tuscan cottage with an heavenly view
4.97 out of 5 average rating, 250 reviews
Villa Capanna, Private Pool, Breathtaking Views
4.89 out of 5 average rating, 309 reviews
Chianti, elegant barn among vineyards and pool
4.95 out of 5 average rating, 181 reviews
Romantic apartment in the Tuscan village
4.89 out of 5 average rating, 343 reviews
Poggio dell'orso.Traditional Casale. Amazing views
4.96 out of 5 average rating, 169 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
4.91 out of 5 average rating, 100 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
4.95 out of 5 average rating, 104 reviews
Separate room, between Cortona and Montepulciano
4.95 out of 5 average rating, 229 reviewsPrivate, pet-friendly home rentals

Stone farmhouse in Val D'Orcia
4.97 out of 5 average rating, 159 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
4.98 out of 5 average rating, 168 reviews
Mafuccio Farmhouse - "Casa di Rigo"
4.95 out of 5 average rating, 124 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
5.0 out of 5 average rating, 116 reviews
La Dimora del Luca
4.98 out of 5 average rating, 171 reviews
Breeder's Room - Triple room breakfast included
5.0 out of 5 average rating, 108 reviews
Tuscan rural house in Mascagni Farmhouse Pienza
5.0 out of 5 average rating, 162 reviews
In Tuscany Rooms
4.96 out of 5 average rating, 137 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 | $141 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





