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Family-friendly vacation rentals in Montalcino

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Montalcino

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

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Top guest favorite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia
4.91 out of 5 average rating, 550 reviews

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Guest favorite
Home in Asciano
4.96 out of 5 average rating, 116 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
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, 109 reviews

Da nonna Ornella - nest in Val d'Orcia

Vista spettacolare e relax assicurato in questo romantico monolocale nel cuore della Val d’Orcia, provincia di Siena, immerso nella splendida Toscana. Ideale per coppie. Dispone di zona living, cucina accessoriata, bagno, riscaldamento, resede, parcheggio privato e un grande e panoramico giardino con lettini e amaca. Vicino a mete iconiche: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d’Orcia, Radicofani, Castiglione d’Orcia e Monte Amiata. Indimenticabile

Top guest favorite
A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.
Home in Montalcino
5 out of 5 average rating, 141 reviews

Montalcino Townhouse with Private Garden & Spa

A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Top guest favorite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 103 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favorite
A cozy bedroom features a wrought-iron bed covered with floral bedding. Soft light is provided by bedside lamps on wooden nightstands. Two windows with wooden shutters offer views of the surrounding greenery, complementing the room’s tranquil atmosphere.
Farm stay in San Quirico d'Orcia
4.96 out of 5 average rating, 101 reviews

Cantagalli Farmhouse, Mugellese Apartment.

L' Agriturismo Cantagalli è una casa in perfetto stile locale di recente ristrutturazione. La stessa è stata realizzata in sostituzione a vecchi capanni agricoli, proprietà di famiglia. Si presenta con rifiniture interne ed esterne di pregio. The Cantagalli Farmhouse is a recently renovated house in perfect local style. The same was built to replace old farm huts, owned by the family, with the intention of creating a farmhouse. It comes with valuable internal and external finishes.

Top guest favorite
A spacious living area features a gray sofa adorned with patterned cushions. A rustic wooden table and bookshelves filled with books are visible in the background, illustrating an inviting open layout that connects the living space to the dining area.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 155 reviews

Apartment in a detached villa - Val d'Orcia

In a cozy independent villa in Tuscan style apartment recently and finely renovated and located in a land rich in history. A few kilometers from the city of art and on the Via Francigena, the apartment can be a base for nature or food and wine tours. From a beautiful terrace overlooking the view you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval Rocca From 03/22/18, the municipal accommodation tax is €2 per person. See additional notes.

Guest favorite
A rustic stone building is surrounded by lush greenery, featuring a staircase leading to a welcoming entrance. Outdoor seating areas are positioned under shaded trees, inviting relaxation. Flower pots add a touch of color to the serene courtyard setting.
Apartment in San Quirico d'Orcia
4.8 out of 5 average rating, 220 reviews

Studio (2+1) in Val d'Orcia - Tuscany

A few steps from the historic center of medieval San Quirico d'Orcia and just 100 meters from the supermarket, a stay made of silence and the quiet passage of time, of days with a relaxing and regenerating atmosphere characteristic of the lifestyle in Val d'Orcia. The Taste of Tranquility is guaranteed by a 5000 sqm park that offers lawns and shady trees suitable for reading or simple relaxation. Ideal for a stay with an "antique" flavor", combined with all modern comforts.

Top guest favorite
Farm stay in San Giovanni d'Asso
4.94 out of 5 average rating, 134 reviews

Flat, Agriturismo "Biofattoria l'Upupa"

The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.

Top guest favorite
A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.
Condo in Montalcino
4.98 out of 5 average rating, 130 reviews

"Landscape Notes" Suite

The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5 out of 5 average rating, 136 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Guest favorite
Home in Montalcino
4.98 out of 5 average rating, 154 reviews

Panoramic nest in Montalcino

A completely independent accommodation recently refurbished - from the design to the furnishings - directly by the host. It is composed of a living room with a fully equipped kitchen and a bedroom with bathroom. The peculiarity of the property is the extremely favorable location in the historic center, with a splendid terrace with panoramic garden on the Val d'Orcia, with barbecue, hammock, sink and outdoor shower.

Popular amenities for Montalcino family-friendly rentals

When is the best time to visit Montalcino?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$34,488 GYDG$34,697 GYDG$38,250 GYDG$41,803 GYDG$42,222 GYDG$45,357 GYDG$48,701 GYDG$51,000 GYDG$46,611 GYDG$43,894 GYDG$43,476 GYDG$45,775 GYD
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Quick stats about vacation rentals that are family-friendly in Montalcino

  • Total vacation rentals

    Explore 530 vacation rentals in Montalcino

  • Nightly prices starting at

    Montalcino vacation rentals start at G$8,361 GYD per night before taxes and fees

  • Verified guest reviews

    Over 14,240 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 310 rentals that welcome pets

  • Vacation rentals with a pool

    280 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    490 of Montalcino vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Montalcino rentals

  • 4.8 Average rating

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

Destinations to explore

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