
Family-friendly vacation 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.

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 years, free for children under 5 years). EV wallbox available.

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.

Separate room, between Cortona and Montepulciano
We are a small farm with a family-run farm on the border between Tuscany and Umbria. The old farmhouse in which we live with our children are surrounded by vineyards and olive groves with a splendid view of Montepulciano. We can sleep in 2 apartments and / or 1 independent room furnished with poor art and originality. In the large garden, available to all, there are two pools (one for children), games, organic vegetable garden. We have a restaurant Pierpaolo cooking the typical Tuscan dishes.

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

Casa Dolce Tuscany ~ Suite & View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A peaceful oasis perfect for those who want to relax and have 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.

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!

Explore nature in the center of Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.
Popular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

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

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

Panoramic Country House in Cortona

Lakehouse in unique position on Lake Trasimeno

La Perla del Lago Holiday home on Lake Trasimeno

Villa Patrizia: Tuscany farmhouse apt 2

Foscolo's Apartment

Casa Bonari - a paradise for the eyes

Secret Garden Siena

Romantic cosy flat - Toscana Italy
Family-friendly home rentals with a pool

Stunning Tuscan Villa & Panoramic Infinity Pool

Tuscany Villa Mammi

Cottage surrounded by nature

Italian Interior

La Foresteria | Granary House

Via della Stella Farmhouse | Casa le Rose

The twigs

Stone farmhouse, exclusive private pool
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$19,035 GYD | G$17,780 GYD | G$24,683 GYD | G$38,071 GYD | G$37,653 GYD | G$47,484 GYD | G$51,249 GYD | G$37,234 GYD | G$34,306 GYD | G$47,066 GYD | G$31,586 GYD | G$26,148 GYD |
| 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 vacation rentals that are family-friendly in Castiglion Fiorentino

Total vacation rentals
Explore 60 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at G$10,459 GYD per night before taxes and fees

Verified guest reviews
Over 1,060 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation 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 vacation rentals include wi-fi 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
- Rentals with a washer and dryer Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Family-friendly rentals Arezzo
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Boboli's Garden
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel
- Palazzo Vecchio
- Stadio Artemio Franchi
- Tenuta Le Velette
- Basilica of St Francis
- Castiglion del Bosco Winery
- Basilica of Santa Croce
- Teatro Tuscanyhall




