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Family-friendly holiday rentals in Monteriggioni

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Monteriggioni

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Top Guest favourite
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, 293 reviews

Podere Vergianoni nestled in Chianti with a pool

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.

Top Guest favourite
A quaint terrace is presented with a small round table and two chairs. Potted flowers add natural color, while a beautiful view of rolling hills and vineyards is visible in the background under a clear blue sky.
Home in Panzano
4.98 out of 5 average rating, 473 reviews

Old Farmhouse near Panzano Castle Abbacìo

The Abbacio apartment is part of an old farmhouse that has been restored respecting the original structure and style. Its location is just on the top of the hill, facing the valley. Surronded by vineyards and olive trees, but also attached to the village. From the house you can easily reach by feet wineries, farms and restaurants. Panzano is halfway between Florence and Siena, easily reached with car. By bus there is a good service from and to Florence, not from and to Siena. A very quiet spot!

Top Guest favourite
A decorative wall shelf is embedded in a stone wall, featuring a small potted plant and a light fixture above. Below the plant, a set of wine glasses is arranged on a glass surface, adding a touch of elegance to the rustic backdrop.
Home in Colle di Val d'Elsa
4.96 out of 5 average rating, 266 reviews

House for the Coast

In the center, a completely renovated, cozy and quiet historic house from the 1300s, equipped with every comfort. Independent entrance, kitchen, living room and bathroom and upstairs double bedroom and bathroom. Located 100 meters from Piazza Arnolfo and 200 meters from the historic center, for those traveling by bus the stop is just 200 meters away. Convenient location for visiting Siena, Florence, San Gimignano, Volterra, Chianti and for walking the Via Francigena or taking the Elsa Trail.

Guest favourite
The stone farmhouse, characterized by a rustic façade, features arched doorways and shuttered windows. Lush greenery surrounds the entrance, offering a serene landscape. A gravel driveway leads to the main entrance, highlighting the spaciousness of the property.
Farm stay in Monteriggioni
4.9 out of 5 average rating, 107 reviews

Podere Casalino - Il Gatto

Nestled near the enchanting Monteriggioni Castle, "Il Casalino" embodies our passion and dedication to restoring a historic farmhouse. My husband and I have poured our hearts into crafting two apartments for rent: Il Gatto and La Pergola. If you have any questions, please reach out to me. Your inquiries are of the utmost importance, and I am committed to promptly responding to your messages. We eagerly anticipate the opportunity to welcome you to "Il Casalino" soon! Best regards, Laura

Guest favourite
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 favourite
A living area is seen with a light-colored sofa facing a flat-screen TV on a wooden unit. A glass coffee table is positioned in front of the sofa, and natural light filters through sheer curtains. A black chair and decorative items are present on shelves.
Condo in Castellina Scalo
4.97 out of 5 average rating, 108 reviews

Above the Post Office

Apartment located in a village in the municipality of Monteriggioni, on the borders of Chianti. The village is located along the ancient Via Francigena. It is about 10 minutes from Siena, Poggibonsi, and Colle di val d'Elsa. It is about 20 minutes from San Gimignano, 40 minutes from Florence, 60 from Pisa and Arezzo. It is possible to move from the village by bus, train, car, bicycle. It is also possible to reach Monteriggioni via a cycle path (20 minutes on foot).

Top Guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Apartment in Poggibonsi
4.99 out of 5 average rating, 304 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

Top Guest favourite
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, 434 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.

Guest favourite
A serene garden setting features a well-maintained lawn with loungers under shaded umbrellas. In the background, a rustic building is partially visible among tall trees, contributing to a tranquil atmosphere. A sign indicates the availability of complimentary wine tasting experiences.
Condo in Monteriggioni
4.86 out of 5 average rating, 135 reviews

Lornano Winery Farm - ''Trebbiano'' villa

4 villas with private garden, private parking, large swimming pool (OPEN FROM 1ST MAY TO 15TH OCTOBER) and park, located within the historic complex of the Fattoria Lornano, immersed in the Chianti hills. Trebbiano is an apartment for two within one of the houses, accessed either from the main piazza or its private garden patio. It is a lovely retreat for a couple wishing to enjoy the wine estate with a touch more privacy.

Top Guest favourite
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 favourite
A rustic rural complex is depicted, featuring a stone building with a terracotta roof. Surrounding greenery enhances the setting, and a gravel path leads to the entrance. The scene is accentuated by a large tree and the clear sky above.
Condo in Monteriggioni
4.93 out of 5 average rating, 136 reviews

Il Vecchio Noce

In the ancient rural complex of Caggio, “Il vecchio noce” offers a fully renovated apartment that can accommodate 2 to 4 people. The complex is located in the heart of the Tuscan countryside, on the Sienese Montagnola, near the medieval village of Monteriggioni and the Via Francigena route.

Guest favourite
A spacious living room is presented with terracotta flooring and wooden beams overhead. A comfortable sofa arrangement surrounds a wooden coffee table, with a flat-screen TV positioned nearby. Natural light filters through the windows, enhancing the inviting ambiance.
Home in Monteriggioni
4.9 out of 5 average rating, 208 reviews

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

Popular amenities for Monteriggioni family-friendly rentals

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