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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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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.

Top guest favorite
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.

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, 266 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, 263 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.

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 scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Apartment in Montemassi
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

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, 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. 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 serene sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light enters through an open window, showcasing views of the surrounding landscape. Two bedside tables hold lamps, and textured wall decor adds a touch of charm.
Apartment in Monteroni d'Arbia
4.98 out of 5 average rating, 215 reviews

"Sunflower" apartment with view of Siena

Caggiolo is a completely renovated farm consisting of several apartments, each with a private entrance and exclusive use of the garden, with a panoramic view of Siena. Located 1 km from Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc). From the farm, you can hike to the Grotti Castle (6 km) or to our pond (2.5 km)

Guest favorite
A serene outdoor area features a swimming pool surrounded by landscaped gardens. A wooden deck with seating overlooks the pool, while a large umbrella provides shade. The two-story villa is positioned above, framed by vibrant greenery and a clear blue sky.
Apartment in Carpineto
4.94 out of 5 average rating, 183 reviews

Tuscan countryside, peace and relaxation 10 minutes from Siena

Our accommodation is close to Siena, therefore to nightlife, the city center but also to the small airport of Ampugnano, parks, and public transport. You'll love our place for its light, the comfort of the bed, the kitchen, the intimacy, and the high ceilings. Our apartment is suitable for couples, solo adventurers, business travelers, families (with children) and furry friends (pets).

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, 235 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!

Top guest favorite
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 471 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Popular amenities for Monticiano family-friendly rentals

When is the best time to visit Monticiano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,661 GYDG$25,869 GYDG$21,906 GYDG$31,919 GYDG$30,042 GYDG$30,876 GYDG$31,711 GYDG$30,042 GYDG$26,287 GYDG$32,963 GYDG$29,833 GYDG$32,545 GYD
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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 G$10,431 GYD 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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