Some info has been automatically translated. Show original language

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.

1 of 1 pages1 / 1
Top guest favourite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Tavarnelle Val di Pesa
4.95 out of 5 average rating, 110 reviews

Casa Luigi Suite with exclusive pool

Come to this apartment: you will be welcomed by centuries of tranquility, and appreciate nature and relaxation. Carefully modernized (and with a swimming pool), this space embodies the roots of good Tuscan living – an equipped olive grove consisting of a pergola with a table and bathroom, a garden with a hammock and in the shade of pine and cypress trees, with chairs, deck chairs and a rocking chair, you can admire the rolling Chianti hills. Courtyard equipped with table and chairs. There is a beautiful elevated swimming pool with some games and a barbecue In addition to the farmhouse, the property includes an olive grove of about 1 hectare, in which equipped spaces have been created for complete relaxation. The Suite has a private entrance that leads directly to the upper floor of the farmhouse, allowing maximum privacy for guests. The farmhouse is part of a small old village inhabited by 4 very discreet and friendly family units. The suite's surface area is 90 square meters and consists of a dining room with kitchenette, large living room, double bedroom, bathroom with shower and a large attic (the door is 1.2 meters wide) with 3 single beds. A very bright environment and immersed in the complete tranquility of the countryside, it is equipped with air conditioning, satellite TV, and free 24-hour Wi-Fi. The owners provide the laundry area. Uncovered private parking. The owners are happy to welcome their guests and are available to resolve any issues. The small village is inhabited by three other very kind and discreet families, ready to help the guest. Tavarnelle is 25 km from Florence, 15 km from San Gimignano, 35 km from Siena. - Images of the exterior, swimming pool, garden and equipped olive grove will be visible soon. We kindly ask you to wait. The accommodation is about 5 km from the center of Tavarnelle. The historic center is equipped with all the services for the citizen and tourist: post office, police, municipality, emergency room, supermarket, trattorias, pizzerias, banks, etc. In addition, in the summer there are various musical events, small craft markets, and finally, every Thursday morning, the classic municipal market takes place. Places of interest (medieval villages) around Tavarnelle: San Donato in Poggio about 12 km. Barberino Val d'Elsa 6 km. Distances from art cities: Tavarnelle - Florence about 25 km Tavarnelle - San Gimignano/Monteriggioni about 20 km Tavarnelle - Siena about 35 km. In the organized outdoor spaces there is an ABOVE GROUND pool, the dimensions are: 10 meters X 5 meters, with a depth of 1.20 meters. A bathroom with shower completes the pool area. In the courtyard, guests have a nice table with barbecue. The entire olive grove area is at their disposal with maximum privacy. The owners, at the guest's request, can book hiking tours or wine-testing tours with the help of professionals. The price of any tour booking is not included in the price of the stay. The small village was once a military fortress, then a parish church or place of worship and from the beginning of the 20th century inhabited by farmers. Today it is inhabited by four very nice and discreet families ready to help the guest. Florence is 15.5 miles away and Siena is 21.7 miles away

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 in Asciano
4.99 out of 5 average rating, 222 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 in Asciano
4.96 out of 5 average rating, 130 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 in Castelnuovo Berardenga
4.92 out of 5 average rating, 336 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 in Asciano
4.95 out of 5 average rating, 99 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
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 151 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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 in Macciano
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.

Top guest favourite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino
4.99 out of 5 average rating, 104 reviews

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

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 Simignano
4.92 out of 5 average rating, 226 reviews

Casa al Gianni - Oak

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favourite
An aerial view captures the extensive grounds of the agriturismo, showcasing a swimming pool surrounded by tall cypress trees and lush green fields. The rustic buildings are nestled among the natural landscape, with rolling hills visible in the background.
Flat in Buonconvento
4.86 out of 5 average rating, 109 reviews

Appaloosa - Apartment for couples and families

Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.

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 in Asciano
4.89 out of 5 average rating, 119 reviews

Charming home Crete Senesi

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

Top guest favourite
The image showcases a serene swimming pool with crystal-clear water reflecting the blue sky. In the background, a rustic two-story house with brick exterior is framed by lush greenery and flowering plants, creating a tranquil setting.
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 199 reviews

Country House in the Crete Senesi

County house deep into the natural reserve that surrounds the village of Chiusure and the Abbey of Monte Oliveto Maggiore. Intimate oasis of relax with private garden and pool located in the heart of Siena's area between Val d'Orcia and Crete Senesi

Popular amenities for Asciano family-friendly rentals

When is the best time to visit Asciano?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$239 SGD$244 SGD$236 SGD$248 SGD$252 SGD$266 SGD$305 SGD$308 SGD$270 SGD$235 SGD$244 SGD$267 SGD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

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 $51 SGD 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