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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 $69 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, 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 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
4.95 out of 5 average rating, 107 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.

KitchenIndoor spacesCleanliness

Top Guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia
4.92 out of 5 average rating, 620 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!

KitchenFamilyCheckout

Guest favourite
A living area features a comfortable gray sofa accompanied by a bright decorative cushion. Light wood flooring complements the simple dining table and chairs. The walls are adorned with framed artwork and mirrors, providing a welcoming ambience.
Apartment in Castiglion Fiorentino
4.93 out of 5 average rating, 14 reviews

Casa Sonia

Casa Sonia is a delightful penthouse on the 4th floor, equipped with an elevator. It is located in a quiet area, a short walk from the historic center of Castiglion Fiorentino, 15 minutes from the Equestrian Centre and Arezzo, and 15 minutes from Cortona. Very close to the train station. Casa Sonia has a double bedroom, a small bedroom and a sofa bed. The kitchen is equipped with all comforts (washing machine, dishwasher, refrigerator, oven and espresso machine) The apartment is equipped with air conditioning.

Indoor spacesNearbyHeating

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
4.9 out of 5 average rating, 240 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

FamilyIndoor spacesCheck-in

Superhost
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
4.99 out of 5 average rating, 523 reviews

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 spacesFamilyBathroom

Top Guest favourite
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
4.99 out of 5 average rating, 88 reviews

Tuscany Villa Mammi

Large, renovated stone villa in the woods of Castiglion Fiorentino, close to Cortona, Arezzo and Siena. A haven of privacy featuring a swimming pool, a panoramic hot tub with breathtaking views of the valley, and table tennis. Enjoy magical evenings under the stars, thanks to the authentic stone barbecue and the wood-fired pizza oven. The ideal getaway for those seeking relaxation, nature and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable holiday.

KitchenIndoor spacesHospitality

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
4.99 out of 5 average rating, 113 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.

FamilyKitchenNearby

Top Guest favourite
Villa in Cortona
4.81 out of 5 average rating, 108 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

KitchenFamilyQuiet

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
4.94 out of 5 average rating, 107 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.

KitchenFamilyBreakfast

Superhost
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
4.92 out of 5 average rating, 104 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.

FamilyKitchenCleanliness

Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano
4.97 out of 5 average rating, 158 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.

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Top Guest favourite
Villa in Arezzo
4.99 out of 5 average rating, 121 reviews

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.

KitchenIndoor spacesCheckout

Popular amenities for Castiglion Fiorentino family-friendly rentals

Family- and pet-friendly home rentals

Top Guest favourite
The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.
Villa in Monte San Savino
4.99 out of 5 average rating, 105 reviews

Villa Tonacato - Charming Villa with private pool

FamilyIndoor spacesBarbecue

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
5.0 out of 5 average rating, 154 reviews

Piazza Grande Boutique Apartment

FamilyIndoor spacesDecor

Top Guest favourite
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
4.97 out of 5 average rating, 245 reviews

Tuscan cottage with an heavenly view

FamilyKitchenBarbecue

Guest favourite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 356 reviews

Apartment in Tuscan farm house.

KitchenFamilyHospitality

Top Guest favourite
The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.
Apartment in Cortona
4.96 out of 5 average rating, 419 reviews

Cortona Shabby Chic House - independent & balcony-

Indoor spacesFamilyCheckout

Top Guest favourite
A dog sits in a grassy area, observing the expansive vineyard landscape that unfolds beyond, featuring rolling hills and rows of grapevines under soft morning light.
Farm stay in Montepulciano
4.95 out of 5 average rating, 225 reviews

Separate room, between Cortona and Montepulciano

FamilyIndoor spacesHospitality

Guest favourite
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
4.96 out of 5 average rating, 25 reviews

Casa La Girandola – Journey through the medieval alleys

FamilyIndoor spacesOutdoor spaces

Top Guest favourite
Villa in Castiglion Fiorentino
5.0 out of 5 average rating, 23 reviews

Beautiful and cozy country-house, sleeps 11

Indoor spacesFamilyAir conditioning

When is the best time to visit Castiglion Fiorentino?

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Avg. price$150 AUD$136 AUD$378 AUD$303 AUD$259 AUD$327 AUD$340 AUD$247 AUD$228 AUD$256 AUD$281 AUD$290 AUD
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