
Family-friendly holiday rentals in Castiglion Fiorentino
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Top-rated family-friendly rentals in Castiglion Fiorentino
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Farmhouse Fattoria La Parita
Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. A basic Italian breakfast (coffee, tea, milk, biscuits, etc.) is included, but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 for 5 to 15 year-olds, free for children under 5). EV wallbox available.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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.

Tuscan charm of villa - countryside
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

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Piazza Grande Boutique Apartment
Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.

Terra Delle Sidhe, Seggiano, Tuscany, Italy
Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Chicca: bright and panoramic in the 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.

Tofanello Turquoise Luxury with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Casa del Passerino
Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

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!
Popular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

"Sunflower" apartment with view of Siena

San Giovanni in Poggio, villa Meriggio 95mq

Villa di Geggiano – Guesthouse

Romantic and with a view. Swimming pool open : )

Luxury Villa with a fantastic view

Tuscan dream in the ancient Tobacco's villa, sauna

Tuscany View - Villa Arianna
Family- and pet-friendly home rentals

The Eagle and the Olive Tree

Cozy apartment in the heart of Tuscany

Villa Patrizia: Tuscany farmhouse apt 2

Cortona Shabby Chic | Halloween offer Oct 22-31

I Tramonti di Eramo, Montepulciano city center.

Piazzale Michelangelo among the olive trees

Your Tuscan oak tree house, enchanting Val d'Orcia
La Piazzetta - Cozy open space in the historic center of Montepulciano
Family-friendly home rentals with a pool

Ortaglia Di Sopra Farm

Stunning Tuscan Villa & Panoramic Infinity Pool

Tuscany Villa Mammi

Charming Apartment with Small Gardens, Pool Access

La Foresteria | Granary House

Via della Stella Farmhouse | Casa le Rose

Podere Il Belvedere Farmhouse - La Stalla

Tuscan countryside, peace and relaxation 10 minutes from Siena
Quick stats about holiday rentals that are family-friendly in Castiglion Fiorentino
Total rentals
60 properties
Nightly prices starting at
$87 NZD before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Rentals with a fireplace Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with a washing machine and dryer Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Villa rentals Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Family-friendly rentals Arezzo
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Uffizi Gallery
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Stadio Artemio Franchi
- Medici Chapels
- Tenuta Le Velette
- Palazzo Vecchio
- Basilica of St Francis
- Basilica di Santa Croce
- Castiglion del Bosco Winery