
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 $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!
Top-rated family-friendly rentals in Castiglion Fiorentino
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

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.

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.

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

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

House at Gianni - Olmo
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!

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.

La Casetta di Brunello, very panoramic with terrace
STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

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!

Apartment Ramerino
Mezzomonte farmhouse is located in one of the most beautiful areas in Chianti, only 33 Km from Firenze and 30 from Siena.We are on the top of the hill ,2km of unmade road from the main street SS222 The farmhouse is immersed in a forest of chestnut and pine trees, surrounded by a completely fenced 6000m2 garden. Our apartments are completaly independent including the private space in the garden.

Charming cottage in Tuscany
Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available

Tuscany House | View Breathtaking
Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.
Popular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

House of Delights - The Medici private leisure house

Villa di Geggiano – Guesthouse

Fontarcella, H&R- mediterranean home with jacuzzi

Villa unesco heritage, Jacuzzi & garden. BB Daria
Wp Relais Villa Vignalunga

Tuscany View - Villa Arianna

Barrel Suite Tuscany • Hot Tub • Vineyard View
Family- and pet-friendly home rentals

Love in Chianti

Tuscan cottage with an heavenly view

Beautiful medieval village!!!

Celeste – The color of the summer sky in Tuscany

Cortona Shabby Chic House - independent & balcony-

In Tuscany Rooms

Poggio Bicchieri Holiday Farm - Memoria apartment
La Piazzetta - Cozy open space in the historic center of Montepulciano
Family-friendly home rentals with a pool

Panoramic Country Suite Montalcino

Tuscany Villa Mammi

Cottage surrounded by nature

Casale Il Trecento

Charming apartment with small gardens, pool access

Relaxing-unspoiled country place Il Monte...

Beautiful medieval tower in Chianti

"L'Assolata" Cottage in Tuscany
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 SGD | $126 SGD | $350 SGD | $234 SGD | $232 SGD | $292 SGD | $316 SGD | $229 SGD | $211 SGD | $237 SGD | $260 SGD | $269 SGD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Villa rentals Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- Rentals with a washing machine and dryer Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Flat rentals Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Family-friendly rentals Arezzo
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mercato Centrale
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Centro Storico Orvieto
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Parco delle Cascine
- Basilica of St Francis
- Medici Chapel
- Basilica of Santa Croce
- Piazza della Signoria
- Del Chianti
- Stadio Artemio Franchi





