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Family-friendly vacation rentals in Monticiano

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Monticiano

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 297 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Guest favorite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 107 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
Apartment in Caminino
4.91 out of 5 average rating, 183 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Guest favorite
A comfortable gray sofa with accent pillows is placed in a spacious living area. A coffee table sits in front, adorned with a small vase of flowers and decorative items. Natural light enters through a nearby window, highlighting the warm terracotta floor.
Apartment in Casciano
4.89 out of 5 average rating, 103 reviews

Casa Marino

Our cozy home is located closed to Siena, the Val d'Arbia and the Val d'Orcia, Unesco World Heritage site; you can easily reach the most beautiful town around Siena and Florence, like San Gimignano, Volterra, Montalcino. Rooms are wide and comfortable. The apartament is bright and you can enjoy a nice view on the Tuscan countryside from its windows. It is located in the old hamlet of Casciano. Suitable for couples and families with kids. Parking area about 50 metres from the apartment.

Guest favorite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.95 out of 5 average rating, 267 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top guest favorite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay in Seggiano
4.99 out of 5 average rating, 265 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Top guest favorite
An aerial view captures the expansive green landscape of the Tuscan hills. A cluster of rustic buildings is visible, surrounded by lush greenery, with a clear swimming pool nestled in the park. The rolling hills and a blue sky enhance the serene rural setting.
Farm stay in Provincia di Siena
4.98 out of 5 average rating, 196 reviews

La Villa Farmhouse - Chestnut, Pool & Garden

Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

Guest favorite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari
4.94 out of 5 average rating, 163 reviews

La Casa del Frantoiano - Pari -

We offer our guests an apartment in Pari, a pretty village in the heart of Tuscany, near the Terme di Petriolo and halfway between Siena and the sea, reachable in about halfanhour. Completely and recently renovated, it consists of a kitchen, a large bedroom, a bathroom, an outdoor relaxation space with a table. Equipped with air conditioning and all kinds of comforts, it is for 2/3 people, in the kitchen there is a single bed. Private pool shared with other guests.

Guest favorite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia
4.94 out of 5 average rating, 184 reviews

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Top guest favorite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 440 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favorite
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.
Condo in Asciano
4.97 out of 5 average rating, 320 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. in our laundry room to those who request it). We recommend a 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 Convenient location to visit Tuscany and Umbria.

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 236 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Popular amenities for Monticiano family-friendly rentals

When is the best time to visit Monticiano?

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Avg. priceﺩ.ﺇ452ﺩ.ﺇ455ﺩ.ﺇ386ﺩ.ﺇ562ﺩ.ﺇ529ﺩ.ﺇ544ﺩ.ﺇ558ﺩ.ﺇ529ﺩ.ﺇ463ﺩ.ﺇ580ﺩ.ﺇ525ﺩ.ﺇ573
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Quick stats about vacation rentals that are family-friendly in Monticiano

  • Total vacation rentals

    Explore 50 vacation rentals in Monticiano

  • Nightly prices starting at

    Monticiano vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 830 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Monticiano vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Monticiano rentals

  • 4.8 Average rating

    Monticiano stays are highly rated by guests—averaging 4.8 out of 5!

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