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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 $118 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, Wifi 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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Top Guest favourite
Villa in Montaione
4.98 out of 5 average rating, 50 reviews

Private Villa with semi-Olympic pool and Tennis

On the ground floor there is a large eat-in kitchen which is very well and functionally equipped with dishwasher, oven, microwave, toaster, kettle, etc. , annexed pantry. The window of the kitchen over the sinks opens into a marvelous Tuscan panorama. Next to the kitchen there is the laundry, with the 2 washing machines and iron equipment. The laundry is shared with the property during your stay. On the other side, still next to the kitchen, there is a dining room with a 10 seats wooden table. Then, there is a large living room with 3 comfortable sofas and there is a sit in fireplace. Due to security reasons the fireplace cannot be used. Totally there are 4 bedrooms: 3 with kings size beds on the first floor and 1 with twin beds on the ground floor. 2 rooms have air conditioning , the remaining 2 have a portable fan. 2 rooms are with en-suite bathrooms with WC, bidet and shower, 1 bathroom with WC, bidet and shower and 1 bathroom with WC. Fresh linen, towels and pool towels are provided weekly. Change of linen and towels for any extra week at € 100. The villa is furnished as a home and the dining and sitting room of the villa are furnished with beautiful antiques and paintings and have old terracotta tiles. So you will not get the feeling of staying in a rented accommodation. Upon prior request we can arrange for 2 extra beds for babies. Outside the villa there is a nice garden with hedges and roses and a beautiful old lime tree under which guests will love to eat their breakfast or dine. In front of the garden there is an ancient and renovated chapel where, once a year, a Mess in memory of the owner's parents is celebrated. Cleaning services are available upon request, also we will bring you the hot dinner (or lunch) when you prefer (even on the day of your arrival) proposing delicious typical Tuscan dishes. Car is needed. We live nearby and are willing to offer you any help you may need. On the top of the nearby hill, 5 minutes walk from the villa, there is the private semi-Olympic pool 25x12.5 m, a pool house with bathroom, changing room, shower, kitchen, dining room, panoramic veranda for relaxing or alfresco dining and a built-in barbecue. Here you can spend most of the time of your vacation as it is a breathless location where you would admire a 360° idyllic typical Tuscan landscape! Just near the private pool, there is a green tennis court for the sole use of guests and a wide lawn where guests can exercise or relax. The pool will be the greatest attraction for all the guests; it will be open June, July, August, September, please ask for May. There is no fence and no surveillance, so children must be supervised at all times as it is up to 4 meter deep in the part of the springboards. In any case guests ' use of the swimming pool is at their own risk. The guests will enjoy their days with long stays at the pool since the pool house provides all comforts of a home. Here you can lean, rest, swim, run, cook, eat, read and appreciate the marvelous surrounding panorama. There are sun loungers, couches, armchairs and tables and a ping pong table. The main attraction of this place is its exclusivity and the possibility to practice sport, i.e. swimming, tennis, ping pong, gym in open lawns or in the large space between the pool and the pool house, soccer. The tennis court can be used anytime. Portable wifi hotspot available at the villa and at the pool and pool house. Notes on prices: Prices for the property (9 sleeps) are meant per day/Euro. They include: villa, private pool and pool house, private tennis, electricity, gas, water, use of the washing machine, firewood, linen, towels, parking Not included: Stay tax € 1.00 per person per day (per max 6 days) for persons over 14 years of age is to be paid directly at arrival. Change of linen and towels for any extra week at € 100, is to be paid directly at arrival. We accept small dogs upon prior agreement and for their stay we ask a contribution of € 10 per day. Check in is from 16.00 to 19.00; late arrivals are possible but we need to be informed in time and they may be charged. Notes: You will be responsible for any damage to the rental property that is caused by you or your party during your stay.

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, 145 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.

Superhost
An outdoor patio area is featured, furnished with a round table and four foldable chairs. A large umbrella provides shade, while a small table made of woven material sits nearby. The garden area is visible, with greenery and flowerpots lining the space.
Home in Montaione
4.76 out of 5 average rating, 399 reviews

La Cantina - Lovely flat in Tuscany

La Cantina is a ground floor apartment in an old restored farmhouse where is living our whole family. It consists of living area with kitchen equipped with refrigerator, stove and oven, TV, WiFi and sofà bed, large double bedroom, bathroom and small utility room with washing machine. The apartment overlooks the private outdoor courtyard with umbrella and chairs. It is located a short walk from the historic center of Montaione and a few kilometers from San Gimignano and Volterra! Also from here you can easily visit the main cities of Tuscany such as Florence, Pisa, Siena and Lucca all an hour away from Montaione. Nearby there is a beautiful golf course, riding stables and you can go hiking in the nature walk and cycling. La Cantina is a small piece of countryside in the village!

Top Guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in loc. Simignano
4.93 out of 5 average rating, 241 reviews

Casa al Gianni - Oak

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
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5.0 out of 5 average rating, 218 reviews

Historic 17th-century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. 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 with a wonderful view of the castle, hills, and vineyards with breathtaking sunsets.

Top Guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 111 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Top Guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 137 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, 229 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.

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, 83 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)

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Superhost
Apartment in Montaione
4.79 out of 5 average rating, 98 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.

Top Guest favourite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property 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 This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Popular amenities for Montaione family-friendly rentals