Some info has been automatically translated. Show original language

Family-friendly holiday 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.

%{current} / %{total}1 / 1
Guest favourite
A living area features a dark blue sofa adorned with decorative pillows. Natural light fills the space through a large window covered with sheer curtains. A dining table is positioned near the window, accompanied by chairs, while a side table and wall units are included in the room.
Home in Montagnano
4.87 out of 5 average rating, 132 reviews

Cozy apartment in the heart of Tuscany

Nestled in the fantastic colors of the Tuscan countryside a few kilometers from the most beautiful medieval villages in Valdichiana such as Arezzo, Cortona, Lucignano and Monte S.Savino, Casa Sossi is only an hour from Florence, Perugia and Siena. Nearby you will find places and activities of interest such as the equestrian center "Arezzo Equestrian Centre", the evocative "Tenuta di Frassineto" and the delicious "Bici Grill Frassineto", ideal for a vacation full of nature. You will feel at home.

Top guest favourite
A dog sits in a grassy area, observing the expansive vineyard landscape that unfolds beyond, featuring rolling hills and rows of grapevines under soft morning light.
Farm stay in Montepulciano
4.95 out of 5 average rating, 202 reviews

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.

Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.91 out of 5 average rating, 223 reviews

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

Top guest favourite
A vibrant garden features an array of colorful flowers, with delicate white blooms prominently displayed. In the background, rolling hills are seen under a dramatic sky, creating a serene landscape filled with natural beauty.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 108 reviews

Da nonna Ornella - nest in Val d'Orcia

Spectacular views and relaxation guaranteed in this romantic studio in the heart of Val d 'Orcia, province of Siena, immersed in beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, private parking and a large and panoramic garden with sun loungers and hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d 'Orcia, Radicofani, Castiglione d 'Orcia, and Monte Amiata. Unforgettable!

Superhost
The image features a serene outdoor space with a swimming pool surrounded by lush olive trees. Comfortable lounge chairs are positioned near the water, and a scenic view of hills and a lake extends in the background under a clear sky.
Place to stay in Terontola Alta
4.81 out of 5 average rating, 149 reviews

Villa Patrizia: Tuscany farmhouse apt 2

Villa Patrizia is the perfect place for a relaxing holiday with your family and for his unique position for someone who wants to enjoy art and historical cities like Cortona, Firenze, Perugia, is a typical Tuscan olive groves, with an amazing view of Trasimeno lake. The apartment offers you every kind of comfort you need. It has a portico, a great outdoors garden and even a big swimming pool where you and your children can spend time relaxing and having fun.The staff is always helpful.

Top guest favourite
A rustic farmhouse is nestled in the Chianti hills, surrounded by lush, well-maintained greenery. The gentle slope of the landscaped garden leads towards the distant rolling hills, creating a serene rural landscape under a clear blue sky.
Farm stay in Greve in Chianti
4.98 out of 5 average rating, 399 reviews

Farmhouse with pool in Chianti

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

Top guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 108 reviews

Casa Dolce Toscana~Suite&View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation,with panoramic views,immersed in the hills of Tuscany. Anoasis of peace perfect for those who want to relax and live 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.

Top guest favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Apartment in Asciano
4.97 out of 5 average rating, 319 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

Top guest favourite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Apartment in Cortona
4.98 out of 5 average rating, 190 reviews

Chicca: bright and panoramic in the historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Top guest favourite
A wooden table is set with two cream-colored cups and a small vase filled with dried wheat and decorative grasses. The white brick wall creates a warm backdrop, enhancing the inviting atmosphere of the dining area.
Flat in Montepulciano
4.99 out of 5 average rating, 271 reviews

Montepulciano Centro Storico

Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. The apartment consists of: entrance, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

Top guest favourite
The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.
Home in Cortona
4.94 out of 5 average rating, 209 reviews

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!

Guest favourite
A charming rural building is set against a backdrop of lush greenery at dusk. Soft lighting highlights the stone exterior and terracotta roof, while the surrounding trees and landscaped grounds enhance the tranquil environment.
Farm stay in Anghiari
4.96 out of 5 average rating, 112 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!

Popular amenities for Castiglion Fiorentino family-friendly rentals

When is the best time to visit Castiglion Fiorentino?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$118 SGD$111 SGD$154 SGD$237 SGD$234 SGD$296 SGD$319 SGD$232 SGD$214 SGD$293 SGD$197 SGD$163 SGD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Quick stats about holiday rentals that are family-friendly in Castiglion Fiorentino

  • Total holiday rentals

    Explore 60 holiday rentals in Castiglion Fiorentino

  • Nightly prices starting at

    Castiglion Fiorentino holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,060 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

  • 4.7 Average rating

    Castiglion Fiorentino stays receive an average rating of 4.7 out of 5 from guests