
Pet-friendly vacation rentals in Castiglion Fiorentino
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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$8,369 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.

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.
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
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
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
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 reviews
Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
4.97 out of 5 average rating, 159 reviews
Cortona Shabby Chic House - independent & balcony-
This is an apartment cared for by a Superhost who lives in Cortona every day. My place is located in the heart of the historic center just a few steps from the main squares and streets This cute apartment is recently renovated and sleeps up to 3 people. Independent apartment with single entrance all on one floor, with balcony. Thoughtfully furnished, equipped with all the comforts for total relaxation
4.96 out of 5 average rating, 423 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
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
The Chianti window
4.9 out of 5 average rating, 135 reviews
Secret Garden Siena
4.98 out of 5 average rating, 221 reviews
Il Vecchio Mulino
4.91 out of 5 average rating, 114 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
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
4.91 out of 5 average rating, 100 reviews
Romantic apartment in the Tuscan village
4.89 out of 5 average rating, 343 reviews
Chianti, elegant barn among vineyards and pool
4.95 out of 5 average rating, 181 reviews
Poggio dell'orso.Traditional Casale. Amazing views
4.96 out of 5 average rating, 169 reviews
Tuscan Barn Apartment for 6 with panoramic pool
4.89 out of 5 average rating, 100 reviews
Separate room, between Cortona and Montepulciano
4.95 out of 5 average rating, 229 reviewsPrivate, pet-friendly home rentals

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
Luxury frescoed apartment in the historical center
4.97 out of 5 average rating, 116 reviews
In Toscana Camere
4.96 out of 5 average rating, 137 reviews
La Dimora del Luca
4.98 out of 5 average rating, 171 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 | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$22,387 GYD | G$20,922 GYD | G$23,851 GYD | G$23,014 GYD | G$23,642 GYD | G$24,270 GYD | G$30,337 GYD | G$24,688 GYD | G$28,036 GYD | G$35,986 GYD | G$22,805 GYD | G$22,805 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





