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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.

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Top guest favorite
A spacious exterior view reveals a charming stone house complemented by vibrant sunset lighting. The image showcases an inviting outdoor seating area with two chairs, set against a backdrop of lush hills and the distant glimmer of the lake.
Home in Perugia

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
Guest favorite
A cozy outdoor loggia features two wicker chairs and a round table, framed by rustic stone walls. Breathtaking views of rolling hills and olive trees are visible in the distance, enhancing the serene atmosphere of the space.
Home in Castiglion Fiorentino

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
Top guest favorite
A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.
Apartment in Cortona

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
Guest favorite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

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
Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

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
Top guest favorite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

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
Guest favorite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

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
Top guest favorite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino

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
Guest favorite
Villa in Cortona

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
Top guest favorite
A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.
Apartment in Arezzo

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
Guest favorite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano

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
Guest favorite
The living area features a spacious sectional sofa, a modern television on a low cabinet, and a round dining table surrounded by four chairs. A map artwork adorns the wall, complemented by shelf plants, enhancing the open feel of the apartment.
Apartment in Castiglion Fiorentino

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 reviews

Popular amenities for Castiglion Fiorentino pet-friendly home rentals

Pet-friendly home rentals with a pool

Guest favorite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

WalkabilityOutdoor spacesCleanliness

4.89 out of 5 average rating, 309 reviews
Guest favorite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Vacation home in Castelnuovo Berardenga

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Outdoor spacesPetsParking

4.91 out of 5 average rating, 100 reviews
Top guest favorite
Farm stay in Arezzo

Esplora la natura al centro di Vigneti Chianti

Outdoor spacesPetsValue

4.97 out of 5 average rating, 265 reviews
Top guest favorite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona

Poggio dell'orso.Traditional Casale. Amazing views

WalkabilityOutdoor spacesBathroom

4.96 out of 5 average rating, 169 reviews
Top guest favorite
A charming stone cottage is set among lush green hills, featuring large arched windows and a shaded patio area with outdoor seating. Olive trees surround the property, providing a connection to the natural landscape, while a gravel pathway leads to the entrance.
Villa in Sinalunga

Gli sterpi

Outdoor spacesPetsSleep quality

5.0 out of 5 average rating, 100 reviews
Top guest favorite
An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.
Cottage in Buonconvento

Tuscan Barn Apartment for 6 with panoramic pool

PetsWalkabilityHospitality

4.89 out of 5 average rating, 100 reviews
Top guest favorite
A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.
Villa in Castiglion Fiorentino

Tuscany Villa Mammi

Outdoor spacesWalkabilityGetting around

4.99 out of 5 average rating, 90 reviews
Top guest favorite
Villa in Castiglion Fiorentino

Beautiful and cozy country-house, sleeps 11

Outdoor spacesCheck-inKitchen

5.0 out of 5 average rating, 25 reviews

Private, pet-friendly home rentals

Top guest favorite
Farm stay in Campiglia D'orcia

Poggio Bicchieri Holiday Farm - Poesia Apartment

PetsOutdoor spacesBackyard

4.95 out of 5 average rating, 579 reviews
Top guest favorite
Vacation home in Petrignano

Fontarcella, H&R- mediterranean home with jacuzzi

Outdoor spacesWalkabilityView

4.98 out of 5 average rating, 168 reviews
Top guest favorite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena

Luxury frescoed apartment in the historical center

Outdoor spacesWalkabilityHeating

4.97 out of 5 average rating, 116 reviews
Top guest favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

PetsOutdoor spacesCheckout

5.0 out of 5 average rating, 116 reviews
Top guest favorite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Vacation home in Monticchiello

In Toscana Camere

Outdoor spacesPetsAccess

4.96 out of 5 average rating, 137 reviews
Guest favorite
A charming rural building is set against a backdrop of lush greenery at dusk. Soft lighting highlights the stone exterior and terracotta roof, while the surrounding trees and landscaped grounds enhance the tranquil environment.
Farm stay in Anghiari

Mafuccio Farmhouse - "Casa di Rigo"

Outdoor spacesWalkabilityGetting around

4.95 out of 5 average rating, 124 reviews
Top guest favorite
An aerial view of a stone farmhouse is presented, surrounded by lush greenery. A private garden features various seating arrangements, including loungers and a dining area under a sunshade. A pathway leads to the entrance, emphasizing the rustic charm of the setting.
Apartment in Castiglion Fiorentino

Pendici 15, small apartment

Outdoor spacesPetsComfort

5.0 out of 5 average rating, 41 reviews
Guest favorite
A spacious bedroom features a warm terracotta ceiling with herringbone patterns. Natural light streams in through a window, illuminating the wooden furniture, including a wardrobe and a small table. Air conditioning is also visible, ensuring a comfortable environment.
Apartment in Castiglion Fiorentino

Casa La Girandola – Journey through the medieval alleys

WalkabilityOutdoor spacesLocation

4.96 out of 5 average rating, 25 reviews

When is the best time to visit Castiglion Fiorentino?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$22,396 GYDG$20,931 GYDG$23,862 GYDG$23,024 GYDG$23,652 GYDG$24,280 GYDG$30,350 GYDG$24,699 GYDG$28,048 GYDG$36,002 GYDG$22,815 GYDG$22,815 GYD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C