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Family-friendly holiday rentals in Montaione

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Montaione

  • Total holiday rentals

    Explore 20 holiday rentals in Montaione

  • Nightly prices starting at

    Montaione holiday rentals start at $121 NZD per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Montaione holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Montaione rentals

  • 4.8 Average rating

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

Top-rated family-friendly rentals in Montaione

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

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Guest favourite
The crystal-clear pool reflects the charming stone villa and surrounding olive trees. A wooden table and chairs are visible on a patio, inviting relaxation. Planters with vibrant flowers add color to the landscape, enhancing the serene ambiance of the countryside.
Villa in Gambassi Terme
4.94 out of 5 average rating, 146 reviews

Villa Il Vecchio Pozzo in Tuscany

Surrounded by nature where you can relax with a magnificent view. Gambassi Terme is located in the centre of Tuscany a few kilometres from the main cities of art (Florence, Siena, Pisa). You can also walk to the historic town center and various village festivals and shows are organized during the summer. The apartment consists of kitchen, living room, sofa, fireplace, bathroom, a double bedroom and a dressing room with two single beds. In the back there is a loggia with breathtaking views and the pool with loungers and parasols. The large garden and the proximity to the family garden with pets (chickens, pigeons and ducks) make it an ideal place for a family with children. Nestled in the countryside where you can relax in peace and quiet at the sight of a magnificent view ,but also easily reachable on foot to the center where there are supermarkets,bar. etc.

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
4.93 out of 5 average rating, 292 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Top Guest favourite
Condo in Gambassi Terme
4.99 out of 5 average rating, 130 reviews

Cosy Tuscan Home near Florence & San Gimignano

A WELCOMING NEST where tradition and modern comfort meet. Perfect for those who want to slow down, relax, and experience the most authentic Tuscany, far from the hustle and bustle. Imagine waking up in the heart of a Tuscan village, looking out onto the square, and starting the day with the tranquility and rhythms of the local life. The apartment, completely renovated and tastefully furnished, is located in the historic center of Gambassi Terme, a strategic point for exploring the wonders of Tuscany.

Guest favourite
A bright and welcoming main bedroom features a large bed with a layered blanket, complemented by a cozy sofa. An entrance with a large archway leads to the rustic living area. A mirrored wardrobe and windows provide ample natural light, enhancing the ambiance.
Place to stay in Gambassi Terme
4.83 out of 5 average rating, 144 reviews

Authentic among stones and bricks

Do you dream of spending a night in the heart of the Tuscan hills, in front of the warmth of an authentic wood-burning fireplace? 🔥🪵 This property is the ideal situation for you! You will stay in a serene area, away from the urban chaos, in the center of Tuscany about 1 hour by car from the main cities and the sea: • Florence 60km • Siena 52km • Pisa 65km • Volterra 27km • SanGimignano 18km Important note: Underfloor heating is always on from October to April. There is no full kitchen.

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
5.0 out of 5 average rating, 351 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Guest favourite
A private swimming pool is surrounded by lounge chairs, offering a relaxing space. Umbrellas provide shade, and lush greenery frames the area. The villa, with its rustic architecture, stands in the background against a clear blue sky, enhancing the serene outdoor setting.
Villa in Montaione
4.98 out of 5 average rating, 52 reviews

Exclusive villa Lionella with private pool

Villa Lionella is an exclusive residence within 2 hectares of private park with swimming pool and independent entrance and private parking. It consists of a large living room with fireplace, dining room, kitchen with second fireplace, library with sofa bed. Upstairs 5 bedrooms with 3 bathrooms. In the basement billiard room, poker table, fitness area with sauna. Equipped with air conditioning, WiFi, linen and private pool. The villa is for the exclusive use of those who book it only

Top Guest favourite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano
4.98 out of 5 average rating, 127 reviews

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

Top Guest favourite
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 138 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5.0 out of 5 average rating, 233 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top Guest favourite
The stone building features a rustic facade with a covered porch supported by wooden beams. A small dining table and chairs are visible on the porch among landscaped greenery. Shadowing from nearby trees enhances the tranquil surroundings of the property.
Apartment in Montaione
4.87 out of 5 average rating, 85 reviews

Tuscany cottage for 4 people with swimming pool

Situated on the top of a Tuscan hill, in the middle of the olive trees with a breathtaking panoramic 360 ° view. 60 hectares of entirely fenced land. Adjacent to a wonderful golf course (27 holes) and the village of Castelfalfi. Ideal for nature lovers and families with children. Strategic location in the middle of the triangle: Pisa, Florence and Sienna (all less than one hour driving). Close to medieval villages like San Gimignano, Certaldo alto, Volterra (20 min by car)

Superhost
Apartment in Montaione
4.79 out of 5 average rating, 101 reviews

Tenuta Collerucci | Poet's House

Tenuta Collerucci is a charming farmhouse located in the heart of the Tuscan countryside, just 4 km from the Etruscan town of Montaione in the Valdelsa area. Set on a beautiful hill, the estate is surrounded by vineyards and olive groves, offering stunning panoramic views of the Tuscan landscape. The farmhouse features four rustic-style apartments and a delightful swimming pool, making it an ideal retreat for relaxation and enjoying the region’s natural beauty.

Guest favourite
A rustic villa features large glass panels that offer views of the surrounding greenery. The spacious outdoor patio area is equipped with a dining set and lounge chairs. Towering trees and well-maintained grass frame the property under a bright blue sky, enhancing the serene countryside setting.
Home in San Miniato
4.93 out of 5 average rating, 123 reviews

Lovely house in a scenic and paiceful location

This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.

Popular amenities for Montaione family-friendly rentals