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Family-friendly holiday rentals in Castiglion Fiorentino

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Castiglion Fiorentino

  • Total holiday rentals

    Explore 50 holiday rentals in Castiglion Fiorentino

  • Nightly prices starting at

    Castiglion Fiorentino holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,130 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • 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 family-friendly rentals in Castiglion Fiorentino

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
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 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.

KitchenFamilyLong stay

4.95 out of 5 average rating, 108 reviews
Guest favourite
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

Indoor spacesKitchenTV

4.9 out of 5 average rating, 241 reviews
Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Indoor spacesKitchenParking

4.99 out of 5 average rating, 531 reviews
Guest favourite
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.

FamilyKitchenCleanliness

4.95 out of 5 average rating, 146 reviews
Top Guest favourite
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.

KitchenFamilyQuiet

4.99 out of 5 average rating, 116 reviews
Guest favourite
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

Indoor spacesFamilyAccess

4.8 out of 5 average rating, 110 reviews
Top Guest favourite
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.

KitchenFamilyHospitality

5.0 out of 5 average rating, 155 reviews
Top Guest favourite
Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.
Farm stay in Montepulciano

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.

FamilyIndoor spacesBarbecue

4.94 out of 5 average rating, 107 reviews
Guest favourite
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.

KitchenFamilyAccuracy

4.93 out of 5 average rating, 109 reviews
Top Guest favourite
Villa in Arezzo

Tuscany View - Villa Arianna

This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience.  While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.

FamilyKitchenParking

4.99 out of 5 average rating, 123 reviews
Guest favourite
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"

Casa di Rigo is the smallest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Rognosi Mountains nature reserve and nestled at the foot of Monte Castello. A quiet and peaceful place like the streams that cross the valley, where you can find peace, and fully experience nature... in the company of the Valley Kids!

FamilyIndoor spacesBiking

4.95 out of 5 average rating, 124 reviews
Top Guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari

Casa Rosmarino Eco-Wellness Country Home

Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

FamilyKitchenSleep quality

4.99 out of 5 average rating, 273 reviews

Popular amenities for Castiglion Fiorentino family-friendly rentals

Family-friendly home rentals with a hot tub

Top Guest favourite
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

Indoor spacesKitchenView

4.93 out of 5 average rating, 334 reviews
Top Guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

FamilyKitchenAmenities

4.97 out of 5 average rating, 126 reviews
Guest favourite
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.
Holiday home in Castelnuovo Berardenga

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

KitchenIndoor spacesCheck-in

4.91 out of 5 average rating, 100 reviews
Top Guest favourite
Villa in Chianciano Terme

Charming Tuscan Villa in Val d'Orcia with a view

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 130 reviews
Guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona

Casa Dolce Toscana | Panoramic Suite with View

FamilyIndoor spacesNearby

4.98 out of 5 average rating, 184 reviews
Top Guest favourite
Farm stay in Greve in Chianti

Farmhouse in Chianti with Swimming Pool

Indoor spacesFamilyLaundry

4.99 out of 5 average rating, 516 reviews
Top Guest favourite
Holiday home in Petrignano

Fontarcella, H&R- mediterranean home with jacuzzi

FamilyKitchenValue

4.98 out of 5 average rating, 168 reviews
Guest favourite
Home in Asciano

Palazzo Monaci - Pool in the Crete Senesi

Indoor spacesKitchenNearby

4.96 out of 5 average rating, 142 reviews

Family-friendly home rentals with a pool

Guest favourite
A charming stone house with a terracotta roof features a welcoming entryway, shaded by umbrellas and surrounded by colorful flowers. In the background, a serene saltwater infinity pool is framed by landscaped greenery, complementing the tranquil rural setting.
Home in Foiano della Chiana

Conca d'Oro villa with private pool, sleeps 4

Indoor spacesFamilyLong stay

4.92 out of 5 average rating, 173 reviews
Top Guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

La Vignaccia (Farmhouse) - villa w/private pool

KitchenIndoor spacesLayout

4.96 out of 5 average rating, 102 reviews
Guest favourite
The outdoor area features a large swimming pool surrounded by wooden decking and lounge chairs. A spacious villa is visible in the background, nestled among greenery. A covered outdoor kitchen area is also present, ideal for dining and gatherings.
Villa in Castiglion Fiorentino

Villa La Foce

FamilyKitchenAmenities

4.95 out of 5 average rating, 21 reviews
Guest favourite
The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.
Villa in Castiglion Fiorentino

Ortaglia di Sotto Farm

Indoor spacesKitchenPets

4.95 out of 5 average rating, 19 reviews
Guest favourite
The property features a charming rustic stone house and a secondary building set against a backdrop of bright blue skies and scattered clouds. Lush green grass surrounds the structures, enhancing the natural beauty of this tranquil countryside setting.
Villa in Castiglion Fiorentino

Villa il Laghetto with Infinity Pool in Tuscany

FamilyIndoor spacesBathroom

4.96 out of 5 average rating, 56 reviews
Top Guest favourite
Villa in Arezzo

Casa Napoleone - Tuscan Villa w/ pool near Cortona

KitchenFamilyComfort

4.96 out of 5 average rating, 28 reviews
Guest favourite
Aerial view of the estate displaying lush vineyards surrounding an inviting shared pool. The landscaped garden features numerous trees and red sun loungers. Two rustic buildings, one with a tiled roof, are visible, enhancing the serene rural atmosphere.
Condo in Monte San Savino

Casa Bianchini | Duplex 6-bedroom apartment (12 +1

Indoor spacesKitchenPets

4.93 out of 5 average rating, 58 reviews
Top Guest favourite
An expansive outdoor area features a crystal-clear infinity pool surrounded by lush olive trees. Comfortable sun loungers are positioned near the water, while red umbrellas provide shade. The backdrop includes a charming farmhouse and an array of greenery under a bright blue sky.
Farm stay in Arezzo

Villa in Tuscany - infinity pool - 8 bdrm - 7 bth

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 64 reviews

When is the best time to visit Castiglion Fiorentino?

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Avg. price$152 AUD$138 AUD$382 AUD$306 AUD$261 AUD$330 AUD$344 AUD$250 AUD$230 AUD$259 AUD$284 AUD$294 AUD
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