
Family-friendly vacation rentals in Castiglion Fiorentino
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Castiglion Fiorentino

Total vacation rentals
Explore 50 vacation rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 1,130 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

4.8 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 proposed farmhouse is a typical terratetto made of characteristic Tuscan stone, ideal for those who want to spend relaxing holidays immersed in the green hills of Castiglione that surround the small valley of Chio. The turret-style building is arranged over three levels: the usable portion of the building is located on the first floor, with a living/dining room and an 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.
KitchenFamilyAir conditioning
4.95 out of 5 average rating, 108 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
Indoor spacesFamilyAccuracy
4.9 out of 5 average rating, 241 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.
FamilyKitchenPool
4.99 out of 5 average rating, 531 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
KitchenIndoor spacesComfort
4.95 out of 5 average rating, 146 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.
Indoor spacesKitchenGrill
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
KitchenFamilyCleanliness
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.
Indoor spacesFamilyGetting around
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.
FamilyIndoor spacesLayout
4.94 out of 5 average rating, 107 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 spacesKitchenCondition
4.93 out of 5 average rating, 109 reviews
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 spacesFamilyAir conditioning
4.99 out of 5 average rating, 123 reviews
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!
KitchenIndoor spacesLong stay
4.95 out of 5 average rating, 124 reviews
Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.
Indoor spacesFamilyBreakfast
4.99 out of 5 average rating, 273 reviewsPopular amenities for Castiglion Fiorentino family-friendly rentals
Family-friendly home rentals with a hot tub

Amazing Tuscany Villa, FREE parking
Indoor spacesKitchenBackyard
4.93 out of 5 average rating, 334 reviews
Wine Experience Villa in Montepulciano
FamilyKitchenWifi
4.97 out of 5 average rating, 126 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
FamilyKitchenCheck-in
4.91 out of 5 average rating, 100 reviews
Charming Tuscan Villa in Val d'Orcia with a view
FamilyKitchenComfort
4.97 out of 5 average rating, 130 reviews
Casa Dolce Toscana | Panoramic Suite with a View
FamilyKitchenComfort
4.98 out of 5 average rating, 184 reviews
Farmhouse in Chianti with Swimming Pool
FamilyIndoor spacesLaundry
4.99 out of 5 average rating, 516 reviews
Fontarcella, H&R- mediterranean home with jacuzzi
FamilyKitchenAccuracy
4.98 out of 5 average rating, 168 reviews
Palazzo Monaci - Pool in the Crete Senesi
FamilyKitchenLocation
4.96 out of 5 average rating, 142 reviewsFamily- and pet-friendly home rentals

Stone farmhouse in Val D'Orcia
Indoor spacesKitchenQuiet
4.97 out of 5 average rating, 159 reviews
Separate room, between Cortona and Montepulciano
KitchenIndoor spacesBiking
4.95 out of 5 average rating, 229 reviews
Beautiful medieval village!!!
FamilyIndoor spacesHeating
4.99 out of 5 average rating, 473 reviews
Tuscan cottage with an heavenly view
FamilyKitchenGrill
4.97 out of 5 average rating, 251 reviews
Traditional stone house in Tuscany
FamilyIndoor spacesAmenities
4.97 out of 5 average rating, 102 reviews
Pendici 15, small apartment
FamilyKitchenGetting around
5.0 out of 5 average rating, 41 reviews
Tuscany Villa Mammi
FamilyIndoor spacesCondition
4.99 out of 5 average rating, 90 reviews
Beautiful and cozy country-house, sleeps 11
Indoor spacesKitchenView
5.0 out of 5 average rating, 25 reviewsFamily-friendly home rentals with a pool

Conca d'Oro villa with private pool, sleeps 4
Indoor spacesKitchenLaundry
4.92 out of 5 average rating, 173 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Indoor spacesFamilySleep quality
4.96 out of 5 average rating, 102 reviews
Villa La Foce
FamilyKitchenBiking
4.95 out of 5 average rating, 21 reviews
Ortaglia di Sotto Farm
FamilyKitchenSleep quality
4.95 out of 5 average rating, 19 reviews
Villa il Laghetto with Infinity Pool in Tuscany
FamilyKitchenOutdoor spaces
4.96 out of 5 average rating, 56 reviews
Casa Napoleone - Tuscan Villa w/ pool near Cortona
KitchenFamilyAir conditioning
4.96 out of 5 average rating, 28 reviews
Casa Bianchini | Duplex 6-bedroom apartment (12 +1
FamilyKitchenLocation
4.93 out of 5 average rating, 58 reviews
Villa in Tuscany - infinity pool - 8 bdrm - 7 bth
KitchenIndoor spacesPool
5.0 out of 5 average rating, 64 reviewsWhen is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 397 | ﺩ.ﺇ 360 | ﺩ.ﺇ 999 | ﺩ.ﺇ 801 | ﺩ.ﺇ 683 | ﺩ.ﺇ 863 | ﺩ.ﺇ 900 | ﺩ.ﺇ 654 | ﺩ.ﺇ 602 | ﺩ.ﺇ 676 | ﺩ.ﺇ 742 | ﺩ.ﺇ 768 |
| 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
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Medici Chapel





