
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 $70 AUD per night before taxes and fees

Verified guest reviews
Over 1,130 verified reviews to help you choose

Pet-friendly accommodation
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

Wi-Fi availability
50 of Castiglion Fiorentino holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 (small 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 located 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 a shower, all furnished with period-style furniture.
Indoor spacesKitchenBathroom
4.95 out of 5 average rating, 109 reviews
Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
Indoor spacesFamilyAccess
4.92 out of 5 average rating, 626 reviews
Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas
FamilyIndoor spacesValue
4.9 out of 5 average rating, 240 reviews
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.
Indoor spacesFamilyValue
4.99 out of 5 average rating, 532 reviews
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.
KitchenFamilyCheckout
4.97 out of 5 average rating, 251 reviews
Casa Dolce Toscana | Panoramic Suite with 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.
KitchenIndoor spacesTV
4.98 out of 5 average rating, 187 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.
FamilyKitchenGetting around
4.99 out of 5 average rating, 116 reviews
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
KitchenIndoor spacesDecor
4.8 out of 5 average rating, 110 reviews
Piazza Grande Boutique Apartment
Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.
KitchenFamilyBathroom
5.0 out of 5 average rating, 155 reviews
Tuscan farmhouse stay with restaurant and pool
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.
KitchenFamilyPets
4.94 out of 5 average rating, 108 reviews
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.
Indoor spacesKitchenCheck-in
4.93 out of 5 average rating, 109 reviews
Stone farmhouse in Val D'Orcia
19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.
Indoor spacesFamilyLong stay
4.98 out of 5 average rating, 160 reviewsPopular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

Amazing Tuscany Villa, FREE parking
FamilyKitchenComfort
4.92 out of 5 average rating, 337 reviews
Palazzo Monaci - Pool in the Crete Senesi
Indoor spacesFamilyLocation
4.96 out of 5 average rating, 142 reviews
Charming Tuscan Villa in Val d'Orcia with a view
KitchenFamilyBreakfast
4.97 out of 5 average rating, 130 reviews
Villa di Geggiano – Guesthouse
FamilyIndoor spacesLayout
4.99 out of 5 average rating, 155 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
KitchenIndoor spacesBreakfast
4.98 out of 5 average rating, 169 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Indoor spacesFamilyParking
4.91 out of 5 average rating, 100 reviews
Farmhouse in Chianti with Swimming Pool
KitchenFamilyBreakfast
4.99 out of 5 average rating, 516 reviewsWp Relais Villa Vignalunga
FamilyIndoor spacesBreakfast
4.93 out of 5 average rating, 117 reviewsFamily- and pet-friendly home rentals

Separate room, between Cortona and Montepulciano
KitchenFamilyComfort
4.95 out of 5 average rating, 229 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
KitchenFamilyTV
4.92 out of 5 average rating, 359 reviews
Beautiful medieval village!!!
FamilyKitchenOutdoor spaces
4.99 out of 5 average rating, 474 reviews
La Perla del Lago Holiday home on Lake Trasimeno
Indoor spacesFamilyComfort
4.98 out of 5 average rating, 207 reviews
Casa Rosmarino Eco-Wellness Country Home
Indoor spacesKitchenOutdoor spaces
4.99 out of 5 average rating, 274 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
KitchenFamilyBarbecue
5.0 out of 5 average rating, 116 reviews
Spedaletto Castle, Val d'Orcia, Pienza
FamilyKitchenOutdoor spaces
4.97 out of 5 average rating, 185 reviews
Breeder's Room - Triple room breakfast included
KitchenIndoor spacesAccuracy
5.0 out of 5 average rating, 108 reviewsFamily-friendly home rentals with a pool

La Vignaccia (Farmhouse) - villa w/private pool
KitchenFamilyHeating
4.96 out of 5 average rating, 102 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
KitchenIndoor spacesBiking
4.98 out of 5 average rating, 145 reviews
Conca d'Oro villa with private pool, sleeps 4
KitchenFamilyBiking
4.92 out of 5 average rating, 173 reviews
Beautiful and cozy country-house, sleeps 11
KitchenFamilyCleanliness
5.0 out of 5 average rating, 25 reviews
Villa Degli Olivi
Indoor spacesFamilySleep quality
4.97 out of 5 average rating, 32 reviews
Stunning Tuscan Villa & Panoramic Infinity Pool
FamilyKitchenAir conditioning
5.0 out of 5 average rating, 96 reviews
Charming Cottage with Pool
KitchenFamilyHeating
4.98 out of 5 average rating, 47 reviews
Ortaglia Di Sopra Farm
FamilyKitchenHospitality
4.87 out of 5 average rating, 23 reviewsWhen is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 AUD | $138 AUD | $382 AUD | $306 AUD | $261 AUD | $330 AUD | $344 AUD | $250 AUD | $230 AUD | $258 AUD | $284 AUD | $294 AUD |
| 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
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Medici Chapel





