
Family-friendly holiday rentals in Montalcino
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Montalcino
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm 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 taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

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.

Villa with View for Family & Friends, in Tuscany
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Bruna's House
LA CASA DI BRUNA A finely renovated apartment, furnished with love and attention to detail, is located inside a historic building The entrance opens onto a living room with a very comfortable sofa connected to a large and comfortable kitchen From the living room, we access the terrace overlooking the fortress where you can enjoy wonderful sunsets On the same floor, there is a bathroom and a bright double bedroom Upstairs is the second bathroom and another comfortable bedroom
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.

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.

"Landscape Notes" Suite
The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Podere Pereti Nuovi – Modern Tuscan Villa
Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Panoramic nest in Montalcino
A completely independent accommodation recently refurbished - from the design to the furnishings - directly by the host. It is composed of a living room with a fully equipped kitchen and a bedroom with bathroom. The peculiarity of the property is the extremely favorable location in the historic center, with a splendid terrace with panoramic garden on the Val d'Orcia, with barbecue, hammock, sink and outdoor shower.

Elegant farmhouse Siena
The apartment of 200 square meters is part of a farmhouse of the 1600, it easily accommodates 6 people, it has 3 large bedrooms, a large living room, a kitchen with fireplace, two bathrooms and a breathtaking view, overlooking the Tuscan countryside up to Montalcino .
Popular amenities for Montalcino family-friendly rentals
Family-friendly home rentals with a hot tub

Villa in Montepulciano with a Pool

Villa di Geggiano – Guesthouse

Casa al Gianni - The Simignano Barn

Villa unesco heritage, Jacuzzi & garden. BB Daria

EcoLodge – modern design in a peaceful panoramic location

Exclusive 10 Acre Estate w/ Pool & Olive Grove!

Casa Dolce Toscana | Panoramic Suite with a View

La Casetta di Nise, Private Spa in the Hamlet
Family- and pet-friendly home rentals

agriturismo il poderuccio "sweet apartment"

Celeste – The color of the summer sky in Tuscany

Authentic Tuscan Country House WITH A/C

Magnificent 2 BR with Terrace and Air Conditioning

In Tuscany Rooms

Secret Garden Siena

Luxurious Medieval Tower & Private Concierge

Rural Tuscany | Family farmstay with restaurant
Family-friendly home rentals with a pool

Tuscan cottage with an heavenly view

The Eagle and the Olive Tree

Luxury Hilltop Villa | Infinity Pool, Sauna, View

TUSCANY farm house SWIMMING POOL

Unique view 3 bdr villa with pool & A/C in Pienza

la Balza

Tenuta La Fuga – Cottage with private pool

Classic two-room apartment
Destinations to explore
- Flat rentals Montalcino
- Rentals with an EV charger Montalcino
- Rentals with a fireplace Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with outdoor seating Montalcino
- Luxury rentals Montalcino
- Rentals with a hot tub Montalcino
- Hotel rooms Montalcino
- Bed and breakfasts Montalcino
- Fitness-friendly rentals Montalcino
- Cottage rentals Montalcino
- House rentals Montalcino
- Farm stay rentals Montalcino
- Rentals with a sauna Montalcino
- Apartment rentals Montalcino
- Rentals with pools Montalcino
- Rentals with a patio Montalcino
- Smoking-friendly rentals Montalcino
- Holiday home rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with a washing machine and dryer Montalcino
- Rentals with a firepit Montalcino
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Feniglia
- Parco Regionale Della Maremma
- Del Chianti
- Gulf of Baratti
- Centro Storico Orvieto
- Cascate del Mulino
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Palazzo Pubblico
- Siena Cathedral
- Antinori nel Chianti Classico
- CavallinoMatto
- Ugolino Golf Club
- Mount Amiata
- Terme San Filippo
- Vulci
- Val di Chiana
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Casa Barthel
- Abbey of Monte Oliveto Maggiore
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Food and drink Siena
- Sightseeing Siena
- Tours Siena
- Sports activities Siena
- Art and culture Siena
- Entertainment Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Tours Italy
- Entertainment Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy







