
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 £37 per night before taxes and fees

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Over 1,130 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 small tower
The farmhouse on offer is a typical terratetto (two-storey farmhouse) built from characteristic Tuscan stone, ideal for those looking to enjoy a relaxing holiday surrounded by the green hills of Castiglioncello that encircle the small valley of Chio. The tower-shaped building is arranged over three levels: the usable part of the property is on the first floor, with a living/dining room and a fully equipped kitchen, and on the second floor, with a double bedroom, a twin bedroom and a bathroom with shower, all furnished with period-style furniture.

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.

Cortona’s Rooftop Nest
L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

Charming Tuscan Villa with View forFamily&Friends
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Apartment in Tuscan farm house.
Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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 - 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

Casa Dolce Toscana | Panoramic Suite with a View
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.

Tuscan Villa Luigina with Pool & Panoramic View
If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Modern apartment in the heart of Tuscany
A few steps from Castiglion Fiorentino train station. Ideal for exploring not only this charming medieval city but also other beautiful Tuscan cities, such as Arezzo, Cortona and Siena. The apartment has 1 bathroom and 5 beds, ideal for families or groups of friends. There is also an additional sofa bed for extra guests. It also has a small loggia for relaxing. Its central location allows you to easily find services such as shops, restaurants and bars nearby.
Popular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Amazing Tuscany Villa, FREE parking

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Le Rondini - where it all began

Luxury Villa with a fantastic view

Villa unesco heritage, Jacuzzi & garden. BB Daria

PoggiodoroLoft, Tuscan dream e relax
Wp Relais Villa Vignalunga
Family- and pet-friendly home rentals

Tuscany Villa Mammi

The Eagle and the Olive Tree

Explore nature in the center of Vigneti Chianti

Pendici 15, small apartment

Cortona Shabby Chic House - independent & balcony-

Traditional stone house in Tuscany

Mafuccio Farmhouse - "Casa di Rigo"

Poggio Bicchieri Holiday Farm - Memoria apartment
Family-friendly home rentals with a pool

Ortaglia Di Sopra Farm

Charming Cottage with Pool

Stunning Tuscan Villa & Panoramic Infinity Pool

Private Chianti Cottage, Garden & Vineyard Views

Cottage surrounded by nature

Casale Il Trecento

Casa Bianchini | Duplex 6-bedroom apartment (12 +1

Luxury Hilltop Villa | Infinity Pool, Sauna, View
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £81 | £73 | £203 | £136 | £135 | £170 | £183 | £133 | £123 | £138 | £151 | £156 |
| 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
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- Pet-friendly rentals Castiglion Fiorentino
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- Rentals with a fireplace Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
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- Family-friendly rentals Arezzo
- Family-friendly rentals Tuscany
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- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mercato Centrale
- Stazione Santa Maria Novella
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Centro Storico Orvieto
- Medici Chapel
- Basilica of Santa Croce
- Stadio Artemio Franchi





