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Family-friendly holiday rentals in Castiglion Fiorentino

Find and book unique family-friendly homes on Airbnb

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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Top guest favourite
An aerial view reveals a charming country house nestled among rolling hills. Olive trees and vineyards extend across the landscape, while a winding road leads to the property, which is framed by tall cypress trees and lush greenery.
Apartment in Asciano
4.99 out of 5 average rating, 223 reviews

Pink like the sunset sky

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

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
4.99 out of 5 average rating, 497 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.

Top guest favourite
A charming terrace features a small round table and two white chairs, offering expansive views of the surrounding hills and distant landscape. A walnut tree stands nearby, enhancing the tranquil outdoor space bathed in natural light from the setting sun.
Apartment in Montepulciano
5 out of 5 average rating, 110 reviews

The walnut tree view, Montepulciano

The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

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.
Guest house in Macciano
4.97 out of 5 average rating, 221 reviews

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.

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, 235 reviews

Tuscan charm of villa - countryside - Villa Senaia

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Top 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
4.99 out of 5 average rating, 159 reviews

Casa Dolce Toscana | Panoramic Suites & Views

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Top guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano
5 out of 5 average rating, 500 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in Simignano
4.92 out of 5 average rating, 227 reviews

Casa al Gianni - Oak

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Top guest favourite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Apartment in Cortona
4.99 out of 5 average rating, 209 reviews

Chicca: Cortona's historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Top guest favourite
Villa in Arezzo
4.99 out of 5 average rating, 112 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.

Top guest favourite
Holiday home in Arezzo
4.95 out of 5 average rating, 174 reviews

Chianti, elegant barn among vineyards and pool

Discover a unique sanctuary in Chianti, a historic barn where stone walls meet 80s vintage design. Fall in love with the canopy bedroom, cook in the modern kitchen, and enjoy vineyard views from the living area. Outside, private gazebos and an infinity pool await you in total silence. A perfect blend of Tuscan heritage, sophisticated style, and pure romance."

Top guest favourite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle in Barberino Tavarnelle
4.89 out of 5 average rating, 124 reviews

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Popular amenities for Castiglion Fiorentino family-friendly rentals

When is the best time to visit Castiglion Fiorentino?

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Avg. price$139 SGD$126 SGD$349 SGD$234 SGD$231 SGD$291 SGD$314 SGD$228 SGD$210 SGD$236 SGD$259 SGD$268 SGD
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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 $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,020 verified reviews to help you choose

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    50 of Castiglion Fiorentino holiday rentals include wifi 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!