
Family-friendly holiday rentals in Castiglion Fiorentino
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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

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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, 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 (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 spacesFamilyView

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!
KitchenIndoor spacesPets

Casa Sonia
Casa Sonia is a delightful penthouse on the 4th floor, equipped with an elevator. It is located in a quiet area, a short walk from the historic center of Castiglion Fiorentino, 15 minutes from the Equestrian Centre and Arezzo, and 15 minutes from Cortona. Very close to the train station. Casa Sonia has a double bedroom, a small bedroom and a sofa bed. The kitchen is equipped with all comforts (washing machine, dishwasher, refrigerator, oven and espresso machine) The apartment is equipped with air conditioning.
Indoor spacesAmenitiesCleanliness

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
KitchenFamilyComfort

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.
FamilyKitchenNearby

Tuscany Villa Mammi
Large, renovated stone villa in the woods of Castiglion Fiorentino, close to Cortona, Arezzo and Siena. A haven of privacy featuring a swimming pool, a panoramic hot tub with breathtaking views of the valley, and table tennis. Enjoy magical evenings under the stars, thanks to the authentic stone barbecue and the wood-fired pizza oven. The ideal getaway for those seeking relaxation, nature and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable holiday.
KitchenIndoor spacesQuiet

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.
Indoor spacesKitchenWalkability

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
Indoor spacesKitchenPets

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.
FamilyKitchenComfort

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.
KitchenIndoor spacesAir conditioning

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.
KitchenIndoor spacesBarbecue

Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.
Indoor spacesFamilyDecor
Popular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

Amazing Tuscany Villa, FREE parking
Indoor spacesFamilyValue

Typical Tuscan country house
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Casa Dolce Toscana | Panoramic Suite with View
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Wine Experience Villa in Montepulciano
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Palazzo Monaci - Pool in the Crete Senesi
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Villa di Geggiano – Guesthouse
FamilyKitchenCheck-in

La Pieve - the house next to the church
KitchenFamilyTV
Wp Relais Villa Vignalunga
Indoor spacesFamilyPets
Family- and pet-friendly home rentals

Villa Tonacato - Charming Villa with private pool
KitchenIndoor spacesQuiet

Piazza Grande Boutique Apartment
Indoor spacesFamilySleep quality

Tuscan cottage with an heavenly view
KitchenIndoor spacesSleep quality

Apartment in Tuscan farm house.
FamilyKitchenComfort

Cortona Shabby Chic House - independent & balcony-
FamilyKitchenView

Separate room, between Cortona and Montepulciano
KitchenIndoor spacesParking

Casa La Girandola – Journey through the medieval alleys
FamilyKitchenBathroom

Beautiful and cozy country-house, sleeps 11
Indoor spacesKitchenGetting around
Family-friendly home rentals with a pool

Conca d'Oro villa with private pool, sleeps 4
FamilyKitchenCleanliness

Stunning Tuscan Villa & Panoramic Infinity Pool
KitchenFamilyTV

Villa La Foce
KitchenFamilyQuiet

Villa Degli Olivi
KitchenIndoor spacesCleanliness

Casa Napoleone - Tuscan Villa w/ pool near Cortona
Indoor spacesKitchenBarbecue

Casa Granaio | Ground floor 1-bedroom apartment (2
Indoor spacesKitchenWi-Fi

Ulivi House
LocationPoolView

Luxury Hilltop Villa | Infinity Pool, Sauna, View
FamilyIndoor spacesValue
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $151 AUD | $137 AUD | $380 AUD | $304 AUD | $260 AUD | $328 AUD | $342 AUD | $248 AUD | $229 AUD | $257 AUD | $282 AUD | $292 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
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Basilica of St Francis
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Centro Storico Orvieto
- Mount Amiata
- Medici Chapel
- Basilica of Santa Croce





