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Family-friendly holiday rentals in Asciano

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Asciano

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

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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
4.92 out of 5 average rating, 227 reviews

Casa al Gianni - Oak

Hello, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farmhouse 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 holiday; it’s a return to our roots. This peaceful haven will stay with you forever. We look forward to welcoming you!

Top guest favourite
An aerial view reveals a charming country house nestled among rolling hills. Olive trees and vineyards extend across the landscape, while a winding road leads to the property, which is framed by tall cypress trees and lush greenery.
Apartment
4.99 out of 5 average rating, 223 reviews

Pink like the sunset sky

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

Guest favourite
Home
4.96 out of 5 average rating, 131 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.

Guest favourite
Farm stay
4.92 out of 5 average rating, 337 reviews

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Top guest favourite
An aerial view captures the agriturismo surrounded by lush green fields and rows of tall cypress trees. A shared swimming pool is visible within the landscaped garden, offering a serene spot for relaxation amidst the natural beauty of the Crete Senesi.
Flat
4.95 out of 5 average rating, 100 reviews

Siena - apartment in the countryside near Siena

The Siena apartment for 5 people is located in the Santa Lucia farmhouse (DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is an apartment of about 100 square meters, located on the ground floor, consisting of three bedrooms (one double; one with two beds and one single), a large living room with fireplace, kitchen, two bathrooms with shower. Private outdoor gazebo with table and benches located in a private garden. AIR CONDITIONING in the rooms for a FEE according to consumption.

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house
4.97 out of 5 average rating, 221 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Superhost
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home
4.91 out of 5 average rating, 74 reviews

Family Forest - Pool in the Crete Senesi

Relax with the whole family in our hideaway in Palazzo Monaci in the heart of the Crete Senesi! Our apartment is located in a residence with a swimming pool and breathtaking views, ideal 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 local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft
5 out of 5 average rating, 501 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Top guest favourite
Farm stay
4.94 out of 5 average rating, 137 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 favourite
A yurt is shown at night, illuminated warmly from within. The starry sky features the Milky Way, providing a stunning backdrop. An outdoor seating area with a thatched roof is visible, showcasing a tranquil atmosphere amidst a natural landscape.
Yurt
4.98 out of 5 average rating, 193 reviews

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Romantic glamping for adults, in the heart of the Tuscan countryside. Silver Yurt, 35 m² + private en-suite bathroom, 7 m² + private outdoor wood-fired hot tub* (*EXTRA CHARGE), private relaxation veranda. Heated in winter and air-conditioned in summer. Dinners with delivery directly to the Yurt, available for an even tastier experience (*SURCHARGE*). - Private parking, WiFi - Kitchen with refrigerator, microwave, (NO STOVE) + private outdoor barbecue.

Guest favourite
The exterior of a two-story terraced apartment features warm, rustic brickwork, a private terrace adorned with potted plants, and a wooden dining table surrounded by seating. Lush greenery and scenic hills are visible in the background under a clear blue sky.
Holiday home
4.89 out of 5 average rating, 120 reviews

Charming home Crete Senesi

Less than 15 kilometers from Siena, the terratetto apartment is located in a characteristic Tuscan village on the hill that leads to the suggestive "Site Transitoire". The property is completed by a nice garden overlooking Siena and a comfortable pool.

Top guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay
4.96 out of 5 average rating, 105 reviews

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Popular amenities for Asciano family-friendly rentals

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Avg. priceÂŁ139ÂŁ142ÂŁ138ÂŁ145ÂŁ147ÂŁ155ÂŁ178ÂŁ180ÂŁ157ÂŁ137ÂŁ142ÂŁ156
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Quick stats about holiday rentals that are family-friendly in Asciano

  • Total holiday rentals

    Explore 450 holiday rentals in Asciano

  • Nightly prices starting at

    Asciano holiday rentals start at ÂŁ30 per night before taxes and fees

  • Verified guest reviews

    Over 7,720 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 240 rentals that welcome pets

  • Holiday rentals with a pool

    330 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wifi availability

    400 of Asciano holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Asciano rentals

  • 4.8 Average rating

    Asciano stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Asciano
  6. Family-friendly rentals