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Family-friendly vacation 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 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
An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.
Apartment in Asciano
4.97 out of 5 average rating, 162 reviews

Loggia 1 in farmhouse with shared pool

Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

Guest favorite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 311 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.

Guest favorite
A heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia
4.98 out of 5 average rating, 114 reviews

San Giovanni in Poggio, Villa Meriggio 95 sqm

Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

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 charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 103 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Top guest favorite
A scenic view captures a rustic stone house set amid rolling hills and olive trees. The expansive landscape features golden fields and lush green foliage, with a winding path leading to the home. The sky is clear, enhancing the serene countryside atmosphere.
Condo in Asciano
4.96 out of 5 average rating, 394 reviews

Romantic Yellow apartment in Crete Senesi

Apartment consisting of 1 comfortable double bedroom (it is possible to make 2 single beds on request), fully equipped kitchen, living room, and bathroom. TV, BBQ, (if needed, we have a washing machine available from 9 a.m. to 8 p.m. in our laundry room). A car is recommended as we are in the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

Top guest favorite
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 in Asciano
4.98 out of 5 average rating, 190 reviews

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Romantic Glamping for adults, in the heart of the Tuscan countryside. 35 sqm Yurt Tent + 7 sqm private indoor bathroom + private outdoor wood-fired Jacuzzi* (*SURCHARGE), private relaxation veranda. Heated in winter and air-conditioned in summer. Dinners with delivery directly to the Yurt, available for an even tastier experience (*ADDITIONAL CHARGE* * *). - Private parking, WiFi - Kitchen with fridge, microwave, (NO STOVE) + private outdoor barbecue.

Top guest favorite
A serene sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light enters through an open window, showcasing views of the surrounding landscape. Two bedside tables hold lamps, and textured wall decor adds a touch of charm.
Apartment in Monteroni d'Arbia
4.98 out of 5 average rating, 217 reviews

"Sunflower" apartment with view of Siena

Caggiolo is a completely renovated farm consisting of several apartments, each with a private entrance and exclusive use of the garden, with a panoramic view of Siena. Located 1 km from Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc). From the farm, you can hike to the Grotti Castle (6 km) or to our pond (2.5 km)

Guest favorite
A rustic living area is showcased with exposed wooden beams and terracotta flooring. A floral sofa complements a wooden dining table surrounded by chairs. Natural light fills the space, highlighting a wall-mounted clock and framed artwork. An inviting atmosphere is created by the warm color palette.
Farm stay in Ville di Corsano
4.95 out of 5 average rating, 132 reviews

Archi, Rustic apartment in Tuscany

The Archi apartment preserves the original attic with exposed beams and bricks and a typical decor of Tuscan country houses. It overlooks the brick Aia and is located in front of a medieval tower. 4 UNESCO heritage sites can be reached in a short time: Historic Center of Siena, Historic Center of San Gimignano, Historic Center of Pienza, Val d'Orcia - Washing machine (not included in the price) - Barbecue (wood/charcoal not included)

Top guest favorite
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, 242 reviews

Casa al Gianni - Hut

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!

Guest favorite
An open living space features a cozy double sofa bed in the background, complemented by a small dining area with a white table and red chairs. Decorative shelves display kitchenware against a neutral wall. A door leads to an outdoor area with greenery visible beyond.
Apartment in Asciano
4.86 out of 5 average rating, 130 reviews

IL CANTUCCIO

Bright studio with very comfortable double sofa bed, fully equipped kitchen,bathroom with shower, small veranda and garden. Private entrance and private parking. Located 500 meters from the historic center of Asciano, very close to the train station and supermarket. Pets are allowed.

Popular amenities for Asciano family-friendly rentals

When is the best time to visit Asciano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,381 GYDG$34,728 GYDG$33,891 GYDG$40,586 GYDG$41,214 GYDG$43,515 GYDG$50,000 GYDG$50,419 GYDG$44,143 GYDG$38,494 GYDG$39,958 GYDG$43,724 GYD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Quick stats about vacation rentals that are family-friendly in Asciano

  • Total vacation rentals

    Explore 430 vacation rentals in Asciano

  • Nightly prices starting at

    Asciano vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,590 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 220 rentals that welcome pets

  • Vacation rentals with a pool

    310 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    390 of Asciano vacation rentals include wi-fi 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