
Family-friendly holiday rentals in Asciano
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Asciano
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Loggiato 3 apartment in Tuscany near Siena
The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

Ancient 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. The apartment is furnished in the perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and thoughtful furnishings and products from local artisans that will help you enjoy a pleasant stay . In the large outdoor courtyard you'll find a salt pool on a panoramic terrace with wonderful views of castle hills and vineyards with breathtaking sunsets.

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.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with all the families in this home. The farmhouse consists of two independent apartments with a living room, kitchen, bedroom and bathroom. You won't have to share anything with other guests, as we have arranged everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deckchairs. Nearby Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

San Giovanni in Poggio, villa Meriggio 95mq
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.

Celeste – The color of the summer sky in Tuscany
Apartment consisting of 2 bedrooms (possibility of single or double beds on request) bathroom, living room, kitchen equipped for cooking. (washing machine available from 9 to 20 in our laundry room) Free parking and WiFi Strategic location for visiting the tourist centers of Tuscany. I look forward to showing you the real Tuscany! We are in the countryside, in the heart of the Crete Senesi, a car is recommended to be independent and visit the magnificent Tuscan countryside

Terra Delle Sidhe, Seggiano, Tuscany, Italy
Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

"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)
Popular amenities for Asciano family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

Amazing Tuscany Villa, FREE parking

Beautiful renovated barn in Tuscany

Your Private Tuscan Retreat

Villa di Geggiano – Guesthouse

Nada Home

Fontarcella, H&R- mediterranean home with jacuzzi

La Casetta
Family- and pet-friendly home rentals

Casa del Giardino

Le Splandole Farm – Crete Senesi

I Tramonti di Eramo, Montepulciano city center.

Secret Garden Siena

Suite in Castello di Valle
La Piazzetta - Cozy open space in the historic center of Montepulciano

Stunning Tuscan apartment for 2

At Paola's in Chianti
Family-friendly home rentals with a pool

Affitti Brevi Siena - The heart of Tuscany

Panoramic Country Suite Montalcino

Family Forest - Pool in the Crete Senesi

Cercis - La Palmierina

Podere La Castellina - No. 1 COTTAGE

Charming home Crete Senesi

Podere Guidi

Siena Country Loft Hideway
Quick stats about holiday rentals that are family-friendly in Asciano
Total rentals
420 properties
Nightly prices starting at
$62 AUD before taxes and fees
Total number of reviews
6.7K reviews
Pet-friendly rentals
210 properties allow pets
Rentals with a pool
320 properties have a pool
Rentals with dedicated workspaces
120 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Lake Bolsena
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Uffizi Gallery
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Kite Beach Fiumara
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Stadio Artemio Franchi
- Cala Di Forno
- Medici Chapels
- Tenuta Le Velette
- Palazzo Vecchio