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

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. An Italian basic breakfast (coffee, tea, milk, cookies, etc.) is included, if you prefer a richer and served breakfast at the table, the cost is €15 per person (€10 from 5 to 15 years, free less than 5 years old). Wallbox EV 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

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.

Casa Dolce Toscana~Suite&View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation,with panoramic views,immersed in the hills of Tuscany. Anoasis of peace perfect for those who want to relax and live an authentic experience. Located a few kilometers from Siena and Florence,our accommodation combines rustic charm with all modern comforts. it is in the heart of the historic center of the famous village of Cetona,below the castle ,overlooking the valley and the scent of Tuscany.

Green – The meadows in Tuscany
Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 to 20 which is in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and Wi-Fi Strategic location for visiting Tuscany and Umbria.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

TOWER apartment in small castle near Florence
Romantic, Historically unique, Magical atmosphere, 360 degree views of the countryside and Florence. Great retreat for digital nomads, or simply to retreat from the hustle and bustle. Convenient for Chianti and Tuscany explorations. A/C in 2 rooms. Cooking class and wine tasting available. If you'd like to add more space and comfort, book the TOWER PENTHOUSE: double the space, a large kitchen, another bathroom. Perfect for families!

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

"Red Rose" apartment with view of Siena.

Amazing Tuscany Villa, FREE parking

Romantic and with a view. Swimming pool open : )

Villa di Geggiano – Guesthouse

Luxury Villa with a fantastic view

Poggio dell'orso.Traditional Casale. Amazing views

PoggiodoroLoft, Tuscan dream e relax

La Pieve - the house next to the church
Family- and pet-friendly home rentals

Casa Clara Cortona Cin IT051017c28a6h9glv

Resort Panoramic view - Free parking

Stuart White Tea Central Panoramic & Garden

I Tramonti di Eramo, Montepulciano city center.

Foscolo's Apartment

Romantic cosy flat - Toscana Italy

Stunning Tuscan apartment for 2

Charming house in Cortona, Tuscany
Family-friendly home rentals with a pool

Stunning Tuscan Villa & Panoramic Infinity Pool

Tuscany Villa Mammi

Cottage surrounded by nature

Italian Interior

Family Forest - Pool in the Crete Senesi

Ortaglia di Sotto Farm

La Foresteria | Granary House

Via della Stella Farmhouse | Casa le Rose
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 78 | € 73 | € 101 | € 156 | € 154 | € 194 | € 209 | € 152 | € 140 | € 192 | € 129 | € 107 |
| 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 |
Quick stats about holiday rentals that are family-friendly in Castiglion Fiorentino

Total holiday rentals
Explore 60 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 1,060 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

4.7 Average rating
Castiglion Fiorentino stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Villa rentals Castiglion Fiorentino
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- Family-friendly rentals Arezzo
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Palazzo Vecchio
- Tenuta Le Velette
- Basilica of St Francis
- Stadio Artemio Franchi
- Castiglion del Bosco Winery
- Basilica di Santa Croce
- Teatro Verdi




